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The 147/147 Experience: Every Justin Timberlake Song Ranked From Worst to First

Justin Timberlake has so few solo albums—incredibly, The 20/20 Experience, out today, is just his third full-length LP—and waits so long in between the releases of each, that sometimes it seems like his discography should be comparable with a group like the Sex Pistols or Nirvana, an artist whose musical output was relatively small, but whose impact was so great that their catalog still stands alongside that of any of their more-prolific peers.

Well, we've done the research, and believe us when we say that that's not exactly the case. Despite only having the three solo LP's, JT's musical output over the last two decades—and yes, he's been around for nearly 20 years now, despite still being only 32 years—has, when you factor in his three-plus albums as a member of 'N Sync and his dozens of guest appearances on other artists' records over the years, been rather tremendous both in quality and quantity.

In fact, we counted a staggering 147 commercially released songs that Justin has been on over the years, and as we did with fellow pop legends Taylor Swift and Rihanna on the release dates of their new LPs last year, we're counting down every single one of them, from worst to first. (Because JT's discography is so sizeable, though, we're gonna breeze through the lowest 47, and gradually get a little more in depth from there as we get closer to the top.)

Join us as we look back through the entirety of Justin Timberlake's Hall-of-Fame-worthy discography, and see where all your favorite 'N Sync and JT solo jams (including the ten cuts off 20/20 Experience—12 with bonus tracks!) rank. And as always, let us know where we badly screwed up.

147. "On the Line" ('N Sync, On the Line Soundtrack)

146. "The Lion Sleeps Tonight" ('N Sync, "For the Girl Who Has Everything" B-Side)

145. "If I'm Not the One" ('N Sync, No Strings Attached (Europe Edition))

144. "In Love on Christmas" ('N Sync, Home for Christmas)

143. "You Got It" ('N Sync, 'N Sync)

142. "The First Noel" ('N Sync, Home for Christmas)

141. "Could It Be You" ('N Sync, No Strings Attached (Europe Release))

140. "Somewhere Someday" ('N Sync, Pokemon: The First Movie OST)

139. "Space Cowboy (Yippie-Yi-Ya)" ('N Sync, No Strings Attached)

138. "The Christmas Song (Chestnuts Roasting On an Open Fire)" ('N Sync, Home for Christmas)

137. "This Is Where the Party's At" ('N Sync, No Strings Attached (Europe Edition))

136. "The Only Gift" ('N Sync, Home for Christmas)

Not a ton of songs of interest in our first dozen—all 'N Sync numbers, including a number of Christmas songs and a several Europe-only bonus tracks. The more intriguing songs here would probably be the group's cover of "The Lion Sleeps Tonight," featuring a rare Chris Kirkpatrick lead falsetto vocal, the unsettling "In Love on Christmas" (which attempts to turn "Jingle Bells" into a Jodeci-type sex jam) and the supremely dated "Space Cowboy," which includes the bizarre couplet "Here it comes, millennium / And everybody's talkin' bout Jerusalem."

135. "Giddy Up" ('N Sync, 'N Sync)

134. "Best of My Life" ('N Sync, 'N Sync (German Edition))

133. "U Drive Me Crazy" ('N Sync, 'N Sync (British Edition))

132. "Losing My Way" (Solo, FutureSex/LoveSounds)

131. "Love's in Our Hearts on Christmas Day" ('N Sync, Home for Christmas)

130. "Some Dreams" ('N Sync, 'N Sync (Singapore Edition))

129. "Under My Tree" ('N Sync, Home for Christmas)

128. "You Don't Have to Be Alone (On Christmas)" ('N Sync, How the Grinch Stole Christmas OST)

127. "I Guess It's Christmas Time" ('N Sync, Home for Christmas)

126. "I Need Love" ('N Sync, 'N Sync)

We hit our first JT solo song, with the exceedingly overwrought attempt at social awwreness "Losing My Way," the sole misstep on FutureSex/LoveSounds and arguably Justin's worst number of the last ten years. Aside from that, just a lot more Christmas and bonus fare, though "I Need Love" and "Some Dreams" are both interesting in how much they sound like pop music from an era well before JT's prime, the former a Real McCoy-esque Eurodance jam and the latter a light reggae flirtation that sounds like it could have been on the Free Willy soundtrack. (And no, "U Drive Me Crazy" isn't the same as the Britney song, though it probably could and should have been.)

125. "It's Christmas" ('N Sync, Home for Christmas)

124. "Crazy For You" ('N Sync, 'N Sync)

123. "I'll Be Good For You" ('N Sync, No Strings Attached)

122. "Role Model" (FreeSol, Single)

121. "If Only Through Heaven's Eyes" ('N Sync, Light It Up OST)

120. "Fascinated" (FreeSol, Single)

119. "Everything I Own" ('N Sync, 'N Sync)

118. "Forever Young" ('N Sync, 'N Sync (German Edition))

117. "Here We Go" ('N Sync, 'N Sync)

116. "Home for Christmas" ('N Sync, Home for Christmas)

The first guest appearances show up here, courtesy of rap/rock outfit FreeSol, demonstrative of JT's surprisingly poor taste when it comes to selecting and grooming proteges. (At least he gets to do some super-Auto-Tuned rapping on "Role Model," though his verse won't exactly have you clamoring for an entire Justin mixtape.) Aside from that, there's also the Babyface-penned Fallen Homies ode "If Only Through Heaven's Eyes," and the Bread cover "Everything I Own," one of a handful of soft-rock standards the group would cover in their early days, though not one of the best.

115. "I'll Never Stop" ('N Sync, 'N Sync (Japanese Edition))

114. "Money" (Matt Morris, When Everything Breaks Open)

113. "Nite-Runner" (Duran Duran, The Red Carpet Massacre)

112. "Riddle" ('N Sync, 'N Sync (German Edition))

111. "Spaceship Coupe" (Solo, The 20/20 Experience)

110. "That Girl (Will Never Be Mine)" ('N Sync, On the Line OST)

109. "Bringin' Da Noise"('N Sync, No Strings Attached)

108. "Falling" ('N Sync, On the Line OST)

107. "Where Is the Love?" (Black Eyed Peas, Elephunk)

106. "The Nature" (Talib Kweli, Eardrum)

A lot more guest appearances, including another lame protege (Matt Morris, the manifestation of JT's coffee-house singer/songwriter career fantasies), a valiant-but-ill-fated comeback attempt (Duran Duran's Timbaland-and-Danja-produced Red Carpet Massacre, a disaster for all involved) and another blugh stab at social awareness (The Black Eyed Peas' "Where Is the Love?," somehow a worldwide smash hit). Also the first song from 20/20 (the over-cooked "Spaceship Coupe") and two highest-ranked of the three songs 'N Sync contributed to On the Line, the super-forgettable star vehicle for Sync members Lance Bass and Joey Fatone, which showed why Justin was the only member of the group destined for that particular type of multi-platform mainstream success.

105. "I Never Knew the Meaning of Christmas" ('N Sync, Home for Christmas)

104. "I Believe in You" (Joe, My Name Is Joe)

103. "That's When I'll Stop Loving You" ('N Sync, No Strings Attached)

102. "Celebrity" ('N Sync, Celebrity)

101. "Hole In My Head" (Rihanna, Single)

Our last five before getting into the Top 100 give us the first appearance of 'N Sync's best album—the title track off Celebrity—as well as the first song to appear on two of our every-song-ranked lists (though for what it's worth, it was only #109 from Rihanna's catalogue).

And now, onto the Top 100. For songs #100-91, click NEXT.

Other Pages: 90-81, 80-71, 70-61, 60-51, 50-41, 40-31, 30-21, 20-11, 10-1

100. "3-WAY (THE GOLDEN RULE)"

Found On: The Lonely Island, Non-Album Single

The least funny of JT's three Lonely Island collaborations with comedian Andy Samberg, though it's hard to deny "Your mom says hi, JINX!" or the "HELICOPTER DICK!" bridge, and Lady Gaga is a welcome presence, as always.

99. "WINNER"

Found On: Jamie Foxx, Non-Album Single

There might never be a song more custom-designed to be used in NBA on TNT commercials than Foxx's "Winner," which was decently rousing, but still fell well short of the gold standard set by Fort Minor's "Remember the Name."

98. "WORK IT"

Found On: Nelly's Nellyville

A lesser single from Nelly's smash 2002 album, "Work It" is enjoyable enough Nelly by-the-numbers, with a fun video set at the Playboy Mansion (including a cameo from Hugh Hefner, natch).

97. "MY STYLE"

Found On: The Black Eyed Peas' Monkey Business

A much funkier and less overbearing JT/Peas collab than the far-more-popular "Where Is the Love," though if he wasn't repeatedly shouted out by producer Timbaland, you might never be able to spot that Justin is the one singing the song's hook.

96. "ALL I WANT IS YOU (THIS CHRISTMAS)"

Found On: 'N Sync's Home for Christmas

Another all-too-rare Kirkpatrick lead vocal, with some seriously sweet sax work making the song stand out from the rest of the bland Home for Christmas originals. Co-written by Martin Briley, '80s one-hit wonder for the underrated "Salt in My Tears."

95. "FOR THE GIRL WHO HAS EVERYTHING"

Found On 'N Sync's 'N Sync

A Babyface-style "Money can't buy you love" ballad from the group's first album. Good, but not as good as Backstreet Boys' "All I Have to Give."

94. "THE ONLY PROMISE THAT REMAINS"

Found On: Reba McEntire's Reba Duets

One of the few country dalliances of the Memphis-born Timberlake's career came on this Reba duet, a stark, beautiful ballad that actually could've used a whole lot more JT than the spare backing vocals that he provides.

93. "O HOLY NIGHT"

Found On: 'N Sync's Home for Christmas

Few R&B groups of their era did a capella as well as 'N Sync, and their accompaniment-less rendition of the Christmas standard (featuring the group trading off on lead vocal, climaxing with Kirkpatrick's falsetto) one of the most fun tracks on Home for Christmas.

92. "DANCE 2NIGHT"

Found On: Madonna's Hard Candy

One of two three-way collabs between Madonna, JT and Timbaland on Madge's Hard Candy, and though both were quite funky, it's not surprising that the fairly unmemorable "2night" wasn't the one pulled as a single.

91. "KISS ME AT MIDNIGHT"

Found On: 'N Sync's Home for Christmas

Thoughtful of 'N Sync to take a break from all the Christmas celebrating to give a shoutout to New Year's as well—especially with the "5! 4! 3!..." countdown that begins the track. One of the more useful songs from Home for Christmas, certainly.

For songs #90-81, click NEXT.

Other Pages: 147-101, 80-71, 70-61, 60-51, 50-41, 40-31, 30-21, 20-11, 10-1

90. "JUST GOT PAID"

Found On: No Strings Attached

Some pop songs will be forever cool in whatever niche is currently popular, and Johnny Kemp's New Jack Swing anthem "Just Got Paid" is certainly one of them, a worthy inclusion of cover on 'N Sync's second album. And considering how many copies No Strings Attached sold, Kemp is probably very grateful for the inclusion.

89. "SELIFSH"

Found On: 'N Sync's Celebrity

Pretty lite-sounding for where 'N Sync were elsewhere on their third album, but a very pretty ballad just the same, with a big key change at song's climax—an unfortunately neglected art in 21st-century pop music.

88. "STRAWBERRY BUBBLEGUM"

Found On: The 20/20 Experience

An impressively lush number, and one that unfolds rather beautifully over its first couple minutes—but it just doesn't need to be two movements and eight minutes long when the song's only real lyrical idea is about equating love and sensuality (and possibly oral sex) to chewing gum.

87. "BOUNCE"

Found On: Timbaland's Shock Value

The beat is an absolute monster, and the JT-sung chorus hook of "Bounce / Like yo' ass had the hicuuuuuups..." is obviously awesome. Unfortunately, the song couldn't leave well enough alone, and the second half of the chorus, with JT listing every possible menage-a-trois combination ("It's you on me and me on you / Then you on me and me on you and you on her...") gets very quickly exhausting.

86. "THE TWO OF US"

Found On: 'N Sync's Celebrity

Nice "Strawberry Fields"-like intro, and a cute double-time switch-up when the song gets to the chorus, though there's ultimately not a ton to grab onto here songwise outside of the lithe, bouncy production.

85. "TOGETHER AGAIN"

Found On: 'N Sync's 'N Sync (German Edition)

The production on this one makes it sound more like it's from 1987 than 1997, but the backing harmonies on the chorus are so gorgeous and the pace is so hypnotic that the datedness of it all isn't nearly as much of a problem as you'd imagine from the first few seconds.

84. "I JUST WANNA BE WITH YOU"

Found On: 'N Sync's 'N Sync

One of JT's earliest attempts at the sophisticated loverman thing, with impressively un-embarrassing results considering that Timberlake was still only 16 at the time of recording. Cool syncopated rhythmic backing (and approximation of the classic "Don't Look Any Further" bass line) here too.

83. "ROCKAWAY LIFE"

Found On: Kenna's Make Sure They See My Face

Kenna's career never quite took off the way JT and The Neptunes (producing here) hoped it would, but the dude still wrote some decent indie rock jams, and this one, with Justin pitching in on backing vocals, was about as catchy and head-bopping as any released in 2007.

82. "MERRY CHRISTMAS, HAPPY HOLIDAYS"

Found On: 'N Sync's Home for Christmas

The most enjoyable of the Home for Christmas originals, "Merry Christmas" was a fine choice for the album's lead single, and remains a worthwhile inclusion on contemporary-pop-themed holiday playlists.

81. "MUSIC OF MY HEART"

Found On: Music of the Heart OST

A duet with '80s pop megastar Gloria Estefan, 'N Sync's highest-charting single of the '90s—and a much-bigger hit than the forgettable Meryl Streep movie it soundtracked—is hardly the first song anyone will think of when remembering the group's salad days. But it is nonetheless a perfectly respectable "One Sweet Day"-type pop power ballad (penned by songwriting legend Diane Warren), with a key change that puts "Selfish" to shame.

For songs #80-71, click NEXT.

Other Pages: 147-101, 100-91, 70-61, 60-51, 50-41, 40-31, 30-21, 20-11, 10-1

80. "NOTHIN' ELSE"

Found On: Justified

Stevie Wonder-influenced almost to the point of pastiche, the electric-piano-led "Nothin' Else" is hardly a highlight on Justified, but is still smooth and mysterious enough that it would've blended in just fine on side three or four of Songs in the Key of Life.

79. "MORE THAN A FEELING"

Found On: 'N Sync's 'N Sync (Singapore Edition)

Yes, that "More Than a Feeling." 'N Sync's largely a capella cover of Boston's classic rock standard really shouldn't work as anything except parody, but damn if it doesn't actually come off as a joyful, creative rendition of the brilliant (and possibly indestructible) 1976 anthem.

78. "TAKE IT FROM HERE"

Found On: Justified

A lovely strings-and-acoustic mid-tempo ballad, the kind of song that Justin Bieber just can't wait until his voice is adult enough to carry. Filled with cute little sonic detail—like the sound of JT inhaling deeply after the "I wanna be your air" lyric in the first verse—courtesy of The Neptunes, the primary architects of Timberlake's solo debut.

77. "SEE RIGHT THROUGH YOU"

Found On: 'N Sync's Celebrity

'N Sync's third album was chock full of these incredibly frustrated-sounding kiss-off-type songs, with tense, buzzing, lean production to match. "See Right Through You" probably isn't the best of the bunch, but it does have JC demanding "DOES HE FFFFREAK THE WAY THAT I DO? / 'Coz you know that I know how to!," which is pretty fun.

76. "TUNNEL VISION"

Found On: The 20/20 Experience

Another 20/20 track that starts intriguing, but whose impact is dulled by its unnecessarily long running time. Damn, is it good to hear those classic Timbaland "uh-huh"s on the pre-chorus, though—we had no idea just how much we had missed him.

75. "HALLELUJAH"

Found On: Hope for Haiti Now

A JT duet with singer/songwriter protege Matt Morris on one of the most over-covered songs in history for charity sounds like an even bigger recipe for disaster than an 'N Sync cover of Boston, but the arrangement is a lovely one and Morris and Timberlake (the latter's voice virtually unrecognizable) really blend quite seamlessly together, stately and not too showy. An impressive line item for Justin's vocal resume.

74. "HISTORY OF RAP"

Found On: Jimmy Fallon's Blow Your Pants Off

JT and long-time showbiz bud Jimmy Fallon do a pretty respectable job blowing through three decades or so of hip-hop history, with Timberlake matching Fallon voice-for-voice with his spot-on renditions of Mike D (on the Beastie Boys' "Paul Revere") and Snoop Dogg (on Dr. Dre's "Nuthin' But a 'G' Thang"). The two would repeat the gimmick on Fallon's show three more times, with diminishing but still-fun returns.

73. "LOOSE ENDS"

Found On: Sergio Mendes' Timeless

Legendary pianist Sergio Mendes attempted a Santana-like comeback with Timeless, an album of collaborations with modern-day artists, including JT singing the hook on "Loose Ends," one of the few Justin attempts at showing a social conscience that actually doesn't come off as cringe-worthy—even despite the disappointing-but-unsurprising presence of will.i.am. Nice interpolation of "What's Goin' On," too.

72. "DIGITAL GET DOWN"

Found On: 'N Sync's No Strings Attached

Slightly eye-roll-worthy in its self-conscious 21st-centuriness, but a necessary step in the evolution of 'N Sync (and JT) into pop futurists, and a very ahead-of-its-time deployment of Auto-Tune. Nobody else but Cher, Daft Punk and (for some reason) Kid Rock was using Auto-Tune like that at the turn of the century.

71. "DRESS ON"

Found On: The 20/20 Experience (Deluxe Edition)

A Timbaland guest verse! We're amazed it took until the bonus tracks on 20/20 Experience to get one, but the slinky shuffle of "Dress On" is as good a place as any for it. And the song still clocks in at under five minutes! Legendary restraint for JT here—though even at that blink-and-you'll-miss-it length, Timbo still finds time for another human-beatbox-type hook at the end. Not every song needs one of those, Timothy.

For songs #70-61, click NEXT.

Other Pages: 147-101, 100-91, 90-81, 60-51, 50-41, 40-31, 30-21, 20-11, 10-1

70. "MOTHERLOVER"

Found On: The Lonely Island's Turtleneck & Chain

A lustful mother swap that comes just short of falling into overbearing ughness, and just catchy enough as a mid/late-'00s R&B pastiche to avoid being a one-note bad joke. Plus, "My dad can't satisfy her in the bedroom ever since in he passed away" and "Every Mothers' Day needs a Mothers' Night" are pretty goddamn funny.

69. "CASANOVA"

Found On: Esmée Denters' Outta Here

Of Timberlake's many handpicked younger artists to become commercial disappointments, Denters probably produced the most actually above-average pop music, including the unfaithful-lover lament "Casanova." The song is helped tremendously by a super-cold Danja beat, but Timberlake also gives the song a jolt on the chorus: "I'm trying to tell you sister / He's running around on ya!"

68. "LET'S TAKE A RIDE"

A light Neptunes breeze soundtracking another Justin vocal in which he plays superhero to a wounded PYT—although in this one, there's at least the lyrical switch-up of the girl having been laid off at her job, and not bruised emotionally by an unappreciative ex. Regardless, when the Neptunes are playing it this smooth, the lyrics are fine as long as they don't get too far in the way.

67. "CARRY OUT"

Found On: Timbaland's Shock Value 2

Proof that the hot-girl-as-fast-food extended lyrical metaphor has very limited appeal over an entire song. Still, Justin's hook is supremely catchy, and the clanging beat was one of the last great productions of Timbaland's second golden period, like the world's funkiest signal for a wedding toast.

66. "4 MINUTES"

Found On: Madonna's Hard Candy

Madonna's last enormous radio hit to date, and proof that she could still trend-hop musically with the best of them. Still, "4 Minutes" demonstrated that JT and Timbo were starting to run aground a little creatively, as the song's groaning hook and shuffling beat both reminded of previous, superior collaborations between the two.

65. "STILL ON MY BRAIN"

Found On: Justified

A rare sort of understated nu-soul number from Timberlake, without a big attention-grabbing hook or big vocal swell or anything. Not the most memorable song he's ever done, but sweet and unassuming in a way that few ballads he's done recently are. Where did the Stevie Wonder influence go in your music, JT?

64. "GOOD FOOT"

Found On: Shark Tale OST

A Timbaland/Timberlake collab from in between JT's first two albums, demonstrating the easy, obvious chemistry between the two. Neither appears to be trying all that hard on this one, but that's kind of the charm, as cool seems so effortless for the two—just listen to Timbo's repeated, matter-of-fact protestation "I ain't tryin'a be rude, dude, but we tryin'a tear up the place." Thankfully, the Shark Taleness is contained to a couple off-hand "fish in the sea"-type references.

63. "UP AGAINST THE WALL"

Found On: 'N Sync's Celebrity

A skittering, bouncy sex jam that sounds, like a handful of 'N Sync songs from this period, like it was recorded inside an overactive pinball machine. Interestingly, this was the only song on an 'N Sync album with both JC and JT credited as co-writers, showing the arguable potential of a Lennon/McCartney-type partnership between the group's two most dominant members.

62. "BODY COUNT"

Found On: The 20/20 Experience (Deluxe Edition)

The hook kinda sounds like "Like I Love You" playing in reverse, which is pretty damn cool, and by the time the horns kick in on the chorus, you're wondering why the hell this song was left off the album's proper tracklist. It sort of makes sense by the song's end, though, as "Body Count" doesn't have a lot going lyrically, and the "Make my body count" hook becomes a little grating. Still, a highly worthy addition to the 20/20 Experience.

61. "LAST NIGHT"

Found On: Justified

Again, hardly one of JT's most memorable lyrics, and the song goes about a minute longer than it needs to, but the Neptunes were in such a zone around the Justified era that "Last Night" is borderline essential just for its hypnotic layers of synth-strings and shimmering electric piano. Plus, no song called "Last Night" has ever been less than awesome.

For songs #60-51, click NEXT.

Other Pages: 147-101, 100-91, 90-81, 80-71, 50-41, 40-31, 30-21, 20-11, 10-1

60. "CAN'T BELIEVE IT" (REMIX)

Found On: T-Pain, non-album single

T-Pain's original was one of the more likeable pop songs of the late '00s, a twinkling, minimal ballad with some endearingly quirky lyrics ("I can put you in a mansion / Somewhere in Wiscansin"). Timberlake is very game for the song's fine remix, even playing along with the song's bizarre off-rhyme scheme ("I can see you breathless / Staring out across the bay in Massachusetts") and adopting T-Pain-level Auto-Tune for the first time since "Digital Get Down." Fun stuff.

59. "DEAD AND GONE"

Found On: T.I.'s Paper Trail

"Dead and Gone" quickly became one of the most-overplayed rap hits of the late '00s, but if you didn't get sick of it, then Justin's chorus hook and memorable bridge ("I turn my head to the East...") were probably the reasons why. Why did every song released around then make such a point of neeedless "OH!" and "AY!" shouting, though?

58. "SAILING"

Found On: 'N Sync's 'N Sync

Hey, don't knock it till you try it. "Sailing," originally a soft-rock classic for Christopher Cross in the early '80s, turns out to be a super-fine fit for the gorgeous harmonies and hazy production of early 'N Sync, turning the song into a very worthy late-'90s successor to PM Dawn's "Set Adrift on Memory Bliss." We'd pay ten bucks for an entire 'N Sync-does-Yacht-Rock compilation, for sure.

57. "(GOD MUST HAVE SPENT) A LITTLE MORE TIME ON YOU"

Found On: 'N Sync's 'N Sync

If you can get past the craw-sticking "Your love is like a river, peaceful and deep" lyric, one of the sweeter, better-crafted ballads of Justin's early career, for sure. Also led to one of 'N Sync's earliest cross-genre collaborations, as the group would later back up the legendary country group Alabama on a rendition of the song.

56. "FLOATIN'"

Found On: Charlie Wilson's Charlie, Last Name Wilson

Some smooth soul from Uncle Charlie, with Timberlake doing an impressive job of holding his own on the second verse. Feel-good stuff, though of course will.i.am shows up spitting on the third verse to remind us all that this world is forever imperfect.

55. "(OH NO) WHAT YOU GOT"

Found On: Justified

Timbaland always had a fascination with Eastern music, which popped up occasionally in his work with Justin Timberlake, probably most notably on the flute-heavy "(Oh No) What You Got," a worthwhile interruption of the run of megahits that constitutes the first side of Justin's debut album Justified. You'll be shouting "Oh no! GIRRRRRRLLLL..." along with JT and Tim by song's end, guaranteed.

56. "RELEASE"

Found On: Timbaland's Shock Value

A fun Timbo/Justin jam that just sounds like the two of them kinda getting loose before a serious day's work in the studio. There's not much actual song to speak of here, but as far as warm-up tunes go, it's a blast, with Tim's cartoonishly over-dramatic "I THINK I'M GETTING A CHAARRRGE!!!" exhortations being particularly smile-inducing.

52. "I'M LOVIN' IT"

Found On: Justified (Deluxe Edition)

A decade's worth of over-use of the song's chorus in crappy McDonald's commercials has probably conditioned JT fans to lunge for the "skip" button whenever they hear the "ba-da-ba-baaaa-baaaaa" hook in this one, but the full song is a lost JT gem, wrapped around a classic Neptunes beat, with choppy guitars and slamming drums that demand a physical response of some sort. Even the "ba-da-ba-baaaa-baaaaa" hook is great, if you can listen to it without visualizing the discomfort and pain associated with taking the second-to-last bite of a Big Mac you never really wanted in the first place.

51. "THAT GIRL"

Found On: The 20/20 Experience

The fake "JT and the Tennessee Kids" introduction at the beginning is unnecessary and a little grating, but the song itself is one of 20/20's most enjoyable, a gentle, soothing soul groove with an excellent chorus ("I'm in love with that girl / So don't be mad at me"). And not to belabor the point here, but actually cutting things off before the five-minute mark helps this one out a lot.

For songs #50-41, click NEXT.

Other Pages: 147-101, 100-91, 90-81, 80-71, 70-61, 40-31, 30-21, 20-11, 10-1

50. "I DRIVE MYSELF CRAZY"

Found On: The best ballad from the first 'N Sync album, with an instantly memorable chorus and a literal-minded-but-TRL-beloved video (starring Amber from Clueless!) setting the group in straitjackets in an insane asylum. The key change at the end is obviously a highlight, but the bridge that leads up to it—with the group just going big on harmonized "oooh-ooooh"s and "la la"s—is arguably even better, as is JC's climactic "Crazy!!!" shouting at the end.

49. "LOVE DEALER"

Found On: Esemée Denters' Outta Here

The love-as-drugs extended metaphor is a tired one—though not so tired that JT didn't spend eight minutes with it on a song still to come on this list—but at least Denters casts herself as the villain in this one, dispensing her love like a peddler trying to get customers desperately and self-destructively hooked. It's a cute lyrical twist, and a fantastic JT/Stargate co-produced beat, making Denters kind of sound like an evil Teena Marie. If this song wasn't a hit, it probably just wasn't ever gonna happen for Esmée.

48. "NO STRINGS ATTACHED"

Found On: 'N Sync's No Strings Attached

Another 'N Sync jam from inside a pinball machine—you can hear the group jumping from bumper to bumper in the chorus, for sure—and one of their stronger non-singles from this time period, compact and catchy, showing what a clear zone the group (and their expert team of writers and producers) was in around the turn of the century. They probably would have had a bangin' music video for this one, too.

48. "LET THE GROOVE GET IN"

Found On: The 20/20 Experience

Over a decade after JT's one and only collaboration with Gloria Estefan, he finally puts out a jam that sounds like an audition for the Miami Sound Machine. The latino-influenced funk of "Let the Groove In"—with a little "Wanna Be Startin' Somethin'" for flavor—is a clear highlight of 20/20 for its first three minutes, but again, like much of the album, things become redundant over seven-plus minutes. The groove's gotten in already, Justin, no need to keep forcing it.

47. "(AND SHE SAID) TAKE ME NOW"

Found On: Justified

Another production tour-de-force, courtesy of Timbaland and forgotten co-producer Scott Storch (who Timbo would later call out on another song still to come on this list), with squelchy electric piano and subtle strings and electric guitar combining into one of the most seductive grooves on Justified—needless to say, no small accomplishment. The call-and-response between Timbo and JT on the chorus was further demonstrative of the undeniable chemistry between the two—chemistry Justin never even really shared with his 'N Sync partners.

46. "THIS I PROMISE YOU"

Found On: 'N Sync's No Strings Attached

The ballad third single off No Strings Attached, written by one-time MOR pop/rock great Richard Marx. "Promise" is a ballad worthy of his "Right Here Waiting" in terms of undeniable mainstream competence, adopting a sort of "Truly Madly Deeply"-inspired formula of a light drum shuffle with gently plucked guitar and airy, spacious production. Not forward thinking as some other stuff the group was doing around this time was, but deeply satisfying, nonetheless.

45. "HOOTNANNY"

Found On: Bubba Sparxxx's Deliverance

Man, whatever happened to Bubba Sparxxx? That dude was awesome.

44. "WHY WHEN HOW"

Found On: Justin & Christina

A totally forgotten gem from a totally forgotten split EP that Justin did with Christina Aguilera after Justified, which each artist contributing one new song and a couple remixes to promote their co-billed Justified & Stripped tour. "Why When How" shows an alternate career Justin could've had as an intimate lounge singer of short, sweet love songs if he and Timbaland hadn't decided to conquer the charts and reinvent popular music instead. We're probably better off that he went with the latter, but the former might've been cool too.

43. "DON'T HOLD THE WALL"

Found On: The 20/20 Experience

Of the many long songs on 20/20 Experience, "Wall" maybe comes the closest to justifying its seven-minute running time, perhaps because its groove is so weird and mysterious and hypnotic from the beginning, and probably partly because its B section actually goes to some interesting (but not totally illogical) places. And personally speaking, I could listen to Timbaland commanding "DANCE!...DON'T HOLLLL' DA WALL!!" for hours.

42. "PUSHER LOVE GIRL"

Found On: The 20/20 Experience

The best of the inexcusably long 20/20 songs, because the Prince-inspired falsetto-funk ballad is so perfect for its first five minutes. If it cut off there, "Pusher" might be 10-20 spots higher on this list, but unfortunately we still have to put up with three minutes of bad drug/love-pun rapping and "J-J-J-J-JUNKIE FOR YOUR LOVE!!" exhortations after that. Why, JT, oh why?

41. "SUMMER LOVE"

Found On: FutureSex/LoveSounds

Easily the least memorable of the FS/LS singles, but that's more a compliment to the rest of the album's hits than a knock on "Summer Love," still a very fine futuristic R&B Jam—just one that doesn't contain many mysteries beyond its squelchy synth hook and inspired vocal rhythms on the verse. It shows how ahead of the game JT and Timbaland were on this album that "Summer Love" sounds pedestrian by their standards, though.

For songs #40-31, click NEXT.

Other Pages: 147-101, 100-91, 90-81, 80-71, 70-61, 60-51, 30-21, 20-11, 10-1

40. "SOMETHING LIKE YOU"

Found On: 'N Sync's Celebrity

Rather than just displaying an obvious Stevie Wonder influence, the group actually got Stevie to do a little harmonica-blowing on this ballad off their third album, and Stevie's unmistakable presence, along with a very solid chorus, make this probably the group's best ballad not to be released as a single.

39. "TELL ME, TELL ME...BABY"

Found On: 'N Sync's Celebrity

"Tell Me" is like a more muscular, even harder-hitting version of one of those Darkchild-produced Destiny's Child breakup jams, with the same kind of stop-start rhythms, slamming beats and nervy, pissed-off-sounding vocals. Even though the song is ostensibly a love song, it sounds so testosterone-fueled and aggressive that it's almost a little bit intimidating. Very interesting stuff from the group that was doing "Tearin' Up My Heart" just two albums earlier.

38. "AYO TECHNOLOGY"

Found On: 50 Cent's Curtis

With a lead rapper who felt like giving more of a shit than 50 Cent clearly felt like giving at the late-'00s stage of his career, "Ayo" could've been a stone classic, since it got one of Timbo's finest, most fascinating beats (even if it does crib rather liberally from Crystal Castles' "Courtship Dating"), and a classic JT chorus to boot (even if I've never bothered to consider the full implications of "I'm tired of using technology / Why don't you sit down on top of me?"). Oh well, still quite a jam regardless.

37. "AIN'T NO DOUBT ABOUT IT"

Found On: The Game, non-album single

Even in 2010, The Neptunes and Justin hadn't lost their Justified-era chemistry. The Game got a classic Neptunes beat and a classic JT hook for the lead single to his R.E.D. Album, but for whatever reason—possibly because it was 2010, and the public's once-insatiable appetite for such jams had long since dissipated—it ended up not even making the album. Still, if this was released in 2003, it could've been The Game's "Beautiful." (The Snoop Dogg one, not the Christina one).

36. "JUST DON'T TELL ME THAT"

Found On: 'N Sync's Celebrity

Another pissed-off Celebrity jam, like an unofficial sequel to Strings' "Bye Bye Bye." Not quite as in-your-face as "Tell Me, Tell Me...Baby," but arguably the better, more coherent song, with an excellent chorus hook and production that doesn't distract from the song's message quite so much. (At just three minutes, one of the group's more efficient cuts, as well.)

35. "LOVE SEX MAGIC"

Found On: Ciara's Fantasy Ride

Almost too easy, with Timberlake and Ciara—two of the biggest stars of the '00s—celebrating their own sexiness and general irresistible-ness with this slinky pop tango. It's not much better than it has to be, but that's still pretty damn good, especially on the song's awesome "This is the part where we fall in love..." breakdown section. Quality video too, of course.

34. "SEXY LADIES"

Found On: FutureSex/LoveSounds

The kind of effortlessly flawless electro-funk that JT and Timbo were tossing off with disturbing ease on FutureSex/LoveSounds—technically, "Sexy Ladies" isn't much more than filler on the album, but it's still utterly captivating, as Timbaland's screeching synth hook matches JT's perfectly Prince-ian "I've got sexy laaaadies / Alloverthefloor..." chorus note-for-note, with the popping bass line providing able support underneath. Again, just too easy.

33. "POP"

Found On: 'N Sync's Celebrity

With its wikky-wikky scratching and minorly corny vocal effects, "Pop" hasn't aged as well as some of the other up-tempo cuts on Celebrity, but there's no denying that it was an eye-opener at the time, with 'N Sync's adventurousness with production and song structure—not to mention the opening callout response to the group's haters—showing that maybe there was something a little more to them (and JT in particular) than some of their less ambitious peers.

32. "SHADES"

Found On: Diddy - Dirty Money's Last Train to Paris

One of the most bonkers songs that JT ever appeared on, a six-minute grinder that oscillates between Lil Wayne's stream-of-conscience rambling, Bilal's plaintive romantic pleading and Justin's hit-or-miss attempt at hashtag rapping ("I can read your mind / Professor X / We can press rewind / VHS"). Of course, this is all over a lurching, pulsating, almost frightening-sounding beat, and all while Diddy sporadically pops up to echo sentiments like "Never made love on marmalade." It is like nothing else you will ever hear, and while that might be for the best, it's still an extremely fascinating piece of music.

31. "DAMN GIRL"

Found On: FutureSex/LoveSounds

One of only two non-Timbaland-produced songs on FutureSex, JT doesn't miss a beat with "Damn Girl," the most traditionally funky and soulful number on the album, with one of the best drum tracks he's ever falsetto'd over. (Nice organ work, too.) Co-producer will.i.am can't resist showing up as a guest rapper late in the song—when will America learn?—but his positive contributions behind the decks outweigh his negative contributions on the mic.

For songs #30-21, click NEXT.

Other Pages: 147-101, 100-91, 90-81, 80-71, 70-61, 60-51, 50-41, 20-11, 10-1

30. "I THOUGHT SHE KNEW"

Found On: 'N Sync's No Strings Attached

The stunning a capella closer to the group's second album, with a fantastic and moving lyrical conceit and some of the loveliest harmonies the group ever committed to record. By the way, Chris Kirkpatrick must've gotten so excited whenever he heard the group was gearing up for an a capella number, knowing he'd probably get a shot at splitting the lead for one of the only times on the album. It's a treat for us too, Chris.

29. "SIGNS"

Found On: Snoop Dogg's R&G: Rhythm & Gangsta

JT curses! OK, that's not really the most notable thing about "Signs," one of the Neptunes' best horn-led grooves with an awesome JT falsetto hook (and Charlie Wilson coming in off the bench with an inspired Gap Band lift), but it was kind of a big deal at the time to hear Justin singing "I'm not sure of what I see / Cupid, don't fuck with me." It proved there was no going back to Orlando, at least.

28. "DO YOUR THING"

Found On: 'N Sync's Celebrity

Easily the weirdest song that 'N Sync ever recorded, the closer to the group's third album (and thus technically the last song the group released), without its vocal, "Do Your Thing" could have fit on any number of albums from IDM producers like Aphex Twin and Squarepusher, a minimal, skittering, almost alien-sounding beat that even a pop visionary like Timbaland probably would've blanched at a little. The group rides the beat well, too, making it in an inscrutable and supremely odd but somehow still satisfying closer to their final album. Where you at, producer James Moss? You're kinda awesome, dude.

27. "IT MAKES ME ILL"

The first (and one of the best) of 'N Sync's angry post-breakup songs, with the group really putting it out there with the song's title and lyrics like "I'm glad that I met him, heh / 'Cause now I know the competition's very slim to none." The song's hyper, over-active beat would point the way to the sound of the group's third album, and show that the saccharine hooks and nice-guy sentiments of the group's debut was already well in the rearview.

26. "GIVE IT TO ME"

Found On: Timbaland's Shock Value

The victory lap for Timbaland, JT and Nelly Furtado, and considering that they were the trio most responsible for the sound of popular music in 2006, it was a well-deserved one. None of the three sound like they're trying particularly hard as they deflect shots from haters and even throw a couple back (particularly in Timbo's Scott Storch-busting verse: "I'm a real producer / You just a piano man"), but that's because none of them needed to try all that hard back then, so effortless was their dominance over the pop world. A number-one hit that not that many people really remember, but one well worth revisiting.

25. "TEARIN' UP MY HEART"

Found On: 'N Sync's 'N Sync

The song that cemented 'N Sync as being on the Backstreet Boys' level of popularity, and one of the enduring classics of the whole TRL era. Some of the lyrics are kinda clunky, especially on the chorus, but it's not like it really matters—you know all the words, and you'll sing them at the top of your lungs at a moment's notice whenever and wherever you hear it for the rest of your life.

24. "NEVER AGAIN"

Found On: Justified

JT's no stranger to emotive breakup ballads, but nowhere else in his discography does he sound as emotionally vulnerable as he does on the Justified closer "Never Again"—Justin really sounds like he's fighting back tears as he sings "You didn't say you're sorry / I don't understand..." on the chorus. It's some pretty affecting shit, its sparse arrangement and lack of rhythmic backing track standing in stark contrast to the 12 songs that preceded it on the album, making the song even more of a stunner. Too bad Timberlake never worked with writer/producer Brian McKnight again—there really might've been something there.

23. "UNTIL THE END OF TIME"

Found On: FutureSex/LoveSounds

Prince was a frequent reference point for JT and Timbaland over the course of FutureSex/LoveSounds, but nothing on the album sounds like it was ripped directly from Purple Rain like "Until the End of Time," down to the filtered, echoing drums and the ripping guitar solo on the climax in live performances. Of course, if you know Purple Rain at all, you know what a huge compliment that is, and "End of Time" is positively "Beautiful Ones"-worthy in its approximation of the Purple One's sound. We went with the duet with Beyoncé here, because how often are you going to get Bey and JT on the same song in this life? Both versions are great, though.

22. "CHOP ME UP"

Found On: FutureSex/LoveSounds

From that brief period when Three 6 Mafia were popular enough—Oscar winners!—that it wasn't weird to see them as one of just a handful of guests on a Justin Timberlake album. They're great of course, DJ Paul screaming about "crying rivers like Timbaland and Timberlake," but the song's real star is Timbo, with those Houston-friendly, down-modulated "SCREWWWWED up" and "CHAWP me up" samples that prove the irresistible hook on the chorus. A classic of its time period for so many reasons.

21. "SENORITA"

Found On: Justified

An ideal opener to Justin's first solo album, and one of the best fourth singles ever released off any pop album ever, "Senorita" is absolutely bursting at the seams with perfect pop hooks. You think you've gotten the general idea, and then JT comes up with the male/female call-and-response section, and you realize you're just getting started. Catchy, exapnsive, inclusive and impossibly fun, the fact that "Senorita" doesn't make JT's top twenty should really tell you something about how much great music this guy has been involved in over the years.

For #20-11, click NEXT.

Other Pages: 147-101, 100-91, 90-81, 80-71, 70-61, 60-51, 50-41, 40-31, 10-1

#20. "RIGHT FOR ME"

Found On: Justified

The lost classic off Justified, and one of the Neptunes' all-time most-underrated efforts—a lithe, sashaying beat that proves how great the duo was at doing more with less, using minimal drums, one repeated zooming synth note and the slightest hint of flute to create one of their most immaculate, irresistible beats ever. The fact that they could afford to bury this song on the second half of Justified shows what a historic zone both artist and producer were around this time period.

#19. "FUTURESEX/LOVESOUND"

Found On: FutureSex/LoveSounds

The stomp of the opening title track to JT's second album is a subtle but undeniable one—Justin and Timothy don't demand that you get out of their way, they just know that you're not gonna have a choice. Justin had never sounded this adult before, this confident, this...weirdly patient. With the understated chug of the verses bursting into the smothering synths of the chorus, there was simply no denying it—Timbaland and Timberlake would soon be here, and we would have no choice but to welcome our new pop overlords.

#18. "SUIT & TIE"

Found On: The 20/20 Experience

No, it didn't stun with the new in quite the same way that previous JT lead singles had, but it did prove that when it came to pop singles you heard once that echoed in your head until you heard it a second time, there was still nobody quite like Justin. Months later, we've yet to hear "Suit & Tie" once without having it stuck in our head for at least an hour after—and glad to have it there—and if that's not good enough for us for a lead single, we should probably re-adjust our expectations a little.

#17. "I WANT YOU BACK"

Found On: 'N Sync's 'N Sync

The first we ever heard of Justin, and still one of the more immaculate pop singles he's ever been involved with. Everything about "I Want You Back" is just right, from the subtle harmonies on the second verse to the "You're the one I want / You're the one I need" lead into the climactic chorus, to that booming piano hook that splits up the chorus and the verse. "Tearin" was the bigger MTV hit at the time, but "Back" was always the better song, and remains the finest jam from 'N Sync's diamond-selling first album.

#16. "(ANOTHER SONG) ALL OVER AGAIN"

Found On: FutureSex/LoveSounds

As with "Never Again" on Justified, JT switches it up on the closer to FutureSex/LoveSounds—after spending 11 songs pushing pop music relentlessly forward, he recruits Rick Rubin to go old-school soul on the 12th track, a pitch-perfect take-me-back ballad that again proves Justin's musical and emotional versatility. He's closer to Lady Gaga in his pop instincts, but he could have been Adele too had he wanted to.

15. "WHAT GOES AROUND / COMES AROUND"

Found On: FutureSex/LoveSounds

An epic kiss-off song, and one whose length and multi-part nature (and how little the song suffered for its relative progginess) proved just how far Justin had burst through his ceiling as a pop artist and megastar. The song is a mite too close musically to JT's prior "Cry Me a River" and has a bit too condescending a self-righteous edge to its lyrics for it to be considered as one of his all-time classics, but if this is your album's third single, chances are you're doing pretty OK.

14. "BLUE OCEAN FLOOR"

Found On: The 20/20 Experience

Completing the trilogy of JT album closers that completely flip the script on the albums that preceded them, the gorgeous "Blue Ocean Floor" follows nine tracks of crowd-pleasing, floor-filling funk with a stark, atmospheric, and lyrically obscure ballad in which Justin discretely invites his beloved to meet him at the bottom of the ocean, as guitar plays in reverse and seagulls and cassette-tape sound-effects float above him. It's stunning proof of yet another direction that Timberlake could've gone in his career—that of the more esoteric, sonically adventurous balladeer, like Thom Yorke or Frank Ocean—and the fact that he nails it this beautifully is probably the most impressive thing about the album.

13. "IT'S GONNA BE ME"

Found On: 'N Sync's No Strings Attached

JT's first number one, and (incredibly) the only chart-topper 'N Sync ever had. "It's Gonna Be Me" is an obvious winner from the first time you hear its trademark cascading riff on the intro, following with the robo-croaking voice exhorting "IT'S GONNA BE MEEEEEE..." Remarkably, the song only gets better from there, with a show-stopping and instantly memorable chorus, and a stunning bridge that keeps the song's impressive momentum going all the way to its final chorus. A deserved classic of turn-of-the-century pop.

12. "MIRRORS"

Found On: The 20/20 Experience

Unlike the rest of the eight-minute tracks on 20/20, "Mirrors" actually gets stronger as it goes, not revealing all of its tricks at first, as its guitar-led beat takes hold and multi-tracked chorus worms its way into your heart. The lyrics, while not quite "Blue Ocean Floor"-level obscure, are still impressively thoughtful and poetic for a singer as direct as Justin usually is, and make up a worthy ode to Justin's new bride–even if that bride happens to have starred in an unfortunately high percentage of the worst movies of the 21st century.

11. "DICK IN A BOX"

Found On: The Lonely Island's Incredibad

Several dozen Lonely Island parodies later, most representing diminishing returns, it's hard to remember just how fresh and hilarious Justin and Andy Samberg's original early-'90s R&B sendup was upon its debut back in 2006, back when it was still novel to have Aaron Hall-sounding ballads about giving your dick as a holiday present. Years later, it's still incredibly impressive, though that shock of the new the first time you heard Justin crooning "Kwanza / Dick in a Box!" or "BACKSTAGE AT THE CMA'S A DICK IN A BOOOOOOOXXXXX!!!" might be borderline impossible to impart to future generations.

For the top ten songs, click NEXT.

Other Pages: 147-101, 100-91, 90-81, 80-71, 70-61, 60-51, 50-41, 40-31, 30-21

#10. "GIRLFRIEND"

Found On: 'N Sync's Celebrity

The song that most represented the turning point in Justin Timberlake's career. It was still ostensibly an 'N Sync him, but his is the only vocal you'll specifically recall from the song—even the harmonies just sound like him blending with himself—and the song's angular, addictive Neptunes groove clearly points the way to the sound he'd soon adapt on his own. Given how good and successful "Girlfriend" was, it's no surprise that was the direction Timberlake would take—and no surprise that another Justin would harken back to it ten years later with an adult breakthrough of his own.

#9. "MY LOVE"

Found On: FutureSex/LoveSounds

Proving that comeback single "SexyBack" was no fluke, "My Love" made it two-for-two with the pop mini-masterpieces for JT and Timbo, the song absolutely pulsing with sonic and musical creativity, hypnotic from its opening chopped-up synth riff. Justin had used the falsetto plenty of times before, but never quite this remorselessly, floating above the song's gorgeous beat like a higher pop power, listeners hanging on his every word. T.I.'s verse isn't perfect ("They call me 'candle guy' / Simply 'coz I am on fire"), but he was the obvious guy to get at the time, and the rest of the song can certainly take the hit anyway.

#8. "THE GAME IS OVER"

Found On: 'N Sync's Celebrity

Rather than sounding trapped in a pinball machine like so many of 'N Sync's turn-of-the-century jams, "The Game Is Over" sounds firmly stuck in an '80s video game arcade, with Pac-Man and Donkey Kong-type sound effects popping off irresistibly at virtually every second, feeding brilliantly into the song's general breakup lyrical conceit ("You played yourself," "Try again, 'coz the game is over"), before exploding into a furious Chemical Brothers-type bridge and then the song's climactic final chorus. The result is one of the most creative songs of the boy band era, and one of the greatest 8-bit-inspired pop songs ever released.

#7. "CRY ME A RIVER"

Found On: Justified

The song that established Justin as a solo star every bit on the level he had left with 'N Sync, "Cry Me a River" stands as maybe the most beloved pop kiss-off song of the 21st century not released by someone named Taylor or Adele, an absolutely flawless pop ballad. Every detail of the production and songwriting—from the writing sound effects, to Justin's self-echoing "DON'T ACT LIKE YOU DON'T KNOW IT!" to the way the music momentarily cuts out on the chorus's "HIIIIIMMMM!!!"—is scientifically designed for maximum pop impact, proving for the first time that there's no substitute in pop for when Timbaland and Timberlake get in the lab together.

#6. "LOVESTONED"/"I THINK SHE KNOWS"

Found On: FutureSex/LoveSounds

"Lovestoned" would be a good, possibly great single all on its own, the song's almost entirely beatboxed beat proving more infectious than irritating (unlike most of its type), and Timberlake's perfectly tailored chorus proving a main event worth waiting a couple verses for. But it's the combination with the "I Think She Knows" outro, and the two minutes or so of transition time that connects the two, that really makes the song a special one—there are few moments in '00s pop as transcendent as when the guitar hits for the first time to introduce the "She Knows" section, the Top 40 equivalent of the angelic guitar breakdown section in indie rocker Interpol's "PDA." It just seemed unfair that JT should be able to go this next-level on his friggin' singles.

#5. "ROCK YOUR BODY"

Found On: Justified

Every male pop star born after the year 1970 has some level of Michael Jackson infatuation, and JT was certainly no exception. "Rock Your Body" was probably Justin's best crack at classic MJ, a disco-tinged club banger that the Neptunes' custom-designed to sound like pure Off the Wall good times, complete with a slow-walking bass line, male/female call-and-response vocals, and some absolutely expert-timed handclaps. MJ might not have had a human-beatbox breakdown in any of his classic singles, but somehow it worked for JT. Justified might not have sold 500 billion copies like Thriller, but if you want to compare the albums single-for-single, songs like "Rock Your Body" make it an argument worth having.

#4. "GONE"

Found On: 'N Sync's Celebrity

JT's all-time greatest ballad, and rightfully viewed in retorspect as his solo debut (like "Careless Whipser" was George Michael's solo debut, even though it was technically a Wham! song). There's just nothing in pop history quite like "Gone," the ghostly way the title phrase echoes throughout the chorus, the way the verse subtly shifts key in transitioning to the devestating chorus, the way the beat just dissolves into a sea of eerie harmonies on the bridge...and that's not even getting to the million clever little production tricks, like the tick-ticking of the clock on the second verse, or the silent-film music that inexplicably introduces the track.

Everything about it is just right and totally heartbreaking, and it shows better than any other 'N Sync song why JT—also a co-writer on the song—had too much talent to stay a member in a boy band, even one as good as 'N Sync, for much longer.

#3. "BYE BYE BYE"

Found On: 'N Sync's No Strings Attached

Chances are, if you remember Justin's pre-solo career for only one song, it's "Bye Bye Bye," 'N Sync's best-remembered hit, and the song that, along with Backstreet's "I Want It That Way," defined the turn-of-the-century boy band era. Although "I Want It That Way" is probably the more enduring song, "Bye Bye Bye" was the one that proved there might be a real legacy to the entire era, a far more lyrically and musically complex song than anything that came before it, but with a chorus and lyrical conceit that still screamed CLASSIC POP SONG CLASSIC POP SONG. After this song, every other boy band (including Backstreet) sounded at least one step behind the times, and it was no surprise that it helped propel 'N Sync (and, eventually, their fearless leader) to a sales level that none of the other groups would again manage.

#2. "LIKE I LOVE YOU"

Found On: Justified

Easy to forget now, but there was a time when the success of Justin's solo venture was very far from a sure thing. Official solo debut "Like I Love You" might not have totally and instantaneously dissuaded all doubts—it only peaked at #11 on the charts, and was premiered in a VMAs performance that suggested Timberlake hadn't completely worked out his solo identity yet—but it proved that his music talent was absolutely undeniable, and that his solo success would eventually catch up.

The sheer amount of ideas contained in the under-five-minutes of "Like I Love You" is greater than that of 95% of pop albums—you can hear the song 25 times and still be like "oh right, I forgot about this part of the song" upon 26th listen. Working with an all-time great Neptunes beat and a top-flight guest contribution from rap duo The Clipse, everything Timberlake does here—the falsetto, the spoken-word, the musical call-and-response—works beautifully, proving an innate grasp of the concept and workings of mainstream pop music that nobody else in the 21st century—with the possible exception of Beyoncé—has matched.

#1. "SEXYBACK"

Found On: FutureSex/LoveSounds

Even amidst a back catalog as successful and diverse as JT's, "SexyBack" still stands apart as a signature, singular moment. When the song came out, there were still some lingering doubts about JT's long-term viability—he had disappeared almost completely for the three years following the end of Justified's run, and nobody knew if he'd be able to live up to that album's success upon his eventual return. Well, "SexyBack" put a stop to those concerns, and unlike with "Like I Love You," this time it was instantaneous and total.

From the first time through "SexyBack"—hell, by the end of the first verse—you knew you were listening to a classic, a song that would still be played, referenced and revered decades down the line. The declaration "I'm bringing sexy back," while obviously ridiculous in nature, nonetheless instantly made complete sense coming from Justin, with Timbaland's backing "Yup!" providing all the reinforcement he would need. By the time JT got to crooning "Dirtyyyy baaaaaaabe..." on the pre-chorus (or bridge, if you believe Timbaland's internal road map), you were as in on the first JT comeback as you could possibly be.

And of course, Timbaland had a lot more to do with the song's success than merely introducing the various parts of the song. You forget now, but in 2006, Timbaland had as much to prove as anyone, spending a couple years fading in popularity before hitching his star to Nelly Furtado's return and enjoying the biggest crossover hit of either artist's career with "Promiscuous." But even that couldn't compare to the jolt of "SexyBack," a juggernaut consisting just of a simple two-note synth riff, a bubbling, unstable-sounding beat, and some tension-creating guitar picking. You had no idea what you were listening to with "SexyBack," but it certainly sounded like the future.

Ultimately, "SexyBack" is the reason why we care about Justin Timberlake's second comeback—this time after a six-year absence—as much as we do. Even though all the odds were stacked against him, we were so badly burned the last time we doubted him, we couldn't possibly dare do it again.

Other Pages: 147-101, 100-91, 90-81, 80-71, 70-61, 60-51, 50-41, 40-31, 30-21, 20-11

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