The Best Bad Boy Songs From the '90s

The trendsetting label's most "Notorious" bangers

The Notorious B.I.G. "Juicy"

The Notorious B.I.G. - Juicy (Official Music Video)

From his debut album, Ready to Die, "Juicy" by The Notorious B.I.G. embodied the rags-to-riches story that is synonymous with Hip-Hop. Sampling Mtume's "Juicy Fruit," Biggie recalls his struggles from trying to make ends meet on the streets of Bedstuy, Brooklyn to living in the lap of luxury. "Juicy" is not only one of the most infamous songs released from the label but one of the defining moments in the genre's history.

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Craig Mack "Flava in Ya Ear (Remix)"

Craig Mack - Flava In Ya Ear (Remix) (Official Music Video)

While the Notorious B.I.G. is the first name that comes to mind when you think of Bad Boy Records, it was Craig Mack who had the distinct honor of being the first artist to release music on the label. The original version of "Flava in Ya Ear" would appear on his album Project: Funk da World, but the star-studded remix featuring The Notorious B.I.G., LL Cool J, Busta Rhymes, and Rampage would become more memorable than its predecessor.

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Faith Evans "You Used to Love Me"

Faith Evans - You Used To Love Me (Official Music Video)

Before the release of her self-titled debut album, Faith, Faith Evans would act as a backing vocalist and songwriter for the likes of Mary J. Blige and Usher. Her single "You Used to Love Me" was indicative of the Bad Boy sound that was starting to become a fixture on urban radio at the time. Faith signed to Bad Bad Records in 1994 and would eventually start dating and then marry The Notorious B.I.G.

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112 "Cupid"

112 - Cupid (Official Music Video)

The Atlanta R&B quartet signed to Bad Boy in 1996 and found success with their self-titled debut album. Their first single, "Only You," was the R&B with a Hip-Hop chaser that had become the label's trademark sound. But it was the slow tempo groove of "Cupid" that showed the group's ability to churn out traditional R&B tunes when needed.

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Total " Can't You See?"

Total [feat. The Notorious B.I.G.] - Can't You See (Official Music Video)

Total's first appearance was on the chorus of Biggie's "Juicy" in 1994. The following year Biggie would return the favor by dropping a verse on their debut single, "Can't You See?" The song would go on to peak at #3 on the Billboard Hot R&B/Hip Hop Songs Chart. Over the span of two decades, "Can't You See?" would find life on social media in the form of the "Can't You See?" Challenge.

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The Notorious B.I.G. "Hypnotize"

The Notorious B.I.G. - Hypnotize (feat. Pam Long) (Official Music Video)

Biggie's sophomore album, Life After Death, had a more polished presentation than his debut. The Brooklyn Bravado was still everpresent, but much of Life After Death contained songs more suitable for radio than a robbery. "Hypnotize" catchy repetitive chorus and big-budget video saw Biggie go from a New York MC to an international superstar.

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Mase "24 Hrs to Live"

Mase Feat. Diddy, The Lox, Black Rob & DMX - 24 Hrs. To Live (Official Music Video)

The lead single from Mase's Harlem World, "Feel So Good," stuck true to the Bad Boy Formula of uptempo party tracks with an old school sample. But it was the gritty "24 Hrs to Live" that stands out. The song is a hypothetical look at what Mase and the track's featured artists (The Lox, Black Rob, and DMX) would do if they only had a day left on earth.

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Puff Daddy "I'll Be Missing You"

Puff Daddy [feat. Faith Evans & 112] - I'll Be Missing You (Official Music Video)

Bad Boy would suffer a devastating loss as a label and a family in March of 1997. The Notorious B.I.G. was gunned down after an industry party in Los Angeles. With the loss of their biggest act, Many wondered how Puff's powerhouse would progress. To commemorate his passing, Puff would release "I'll Be Missing You." The song would borrow its bassline and hook from The Police's "Every Breath You Take" and featured 112 and Biggie's wife, Faith.

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The Notorious B.I.G. "Mo Money Mo Problems"

The Notorious B.I.G. - Mo Money Mo Problems (Official Music Video)

Biggie's death sent shockwaves through Hip-Hop. Now burdened with the responsibility of being his own label's lead act, it was also up to Puff to keep Biggie's legacy alive in music. "Mo Money Mo Problems,"' featuring Puff Daddy and Mase, was the second single to be released from Life After Death. Though the party vibe and the extravagant video was a celebration of Biggie's life, the song's title is also a reminder of circumstances in which the world lost him..

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