As those leaves fall and more time is spent indoors, we acquaint ourselves with that character called the sadboi. Evil twin two the more nefarious fuckboi, he has also been called the softboy, the passive ghoster and an all-about pile of feelings that needs to talk to you about them right now. While normally, you'd take that as your cue to GTFO, it's like 30 degrees outside. This is his time, to roast the fire and feast on our feelings. These are his man-tears jams.


Drake: King Sadboi

Drake is King Sadboi like Pusha T is king of pushing cocaine. And like dealings with Mr. Thornton, when the Drake rolls by, you better come correct. With feelings.

He's been loudly holding his feelings in since promising to "give you my all and the next morning you'll forget who" back in 2009. Four albums and a mixtape later, he still "need a girl who gon' love me" and who won't "fight with me at Cheesecake." But six years later, it's still his ominous commitment to "be your friend if you let me/don't wanna come on strong" that retains him that crown on the heart-are-his-sleeve "I Get Lonely Too.":

Kanye: 808s & We Need To Talk

Circa-2008 Kanye could have also very easily had a career as sadboi king, but moved on pretty quickly to be a god and whatnot. But 808s & Heartbreak, however is one near-hour of wintery feelings of the heart. There's much talk now on how 808s essentially invented The Weeknd, Frank Ocean and whatever but that eludes the real frosty work of I'm-really-sad-that-my-then-fiancé-is-on-my-nerve genius that the record is.

Begin talking about feelings with your significant other or two-night stand and be immediately comforted by the logic of Kanye's "Baby, don't worry about it/You worry bout the wrong things..."

Justin Bieber: Faux-Sadboi

Mr. Bieber may be real sadboi, after all those people were mean to him about his inability to meaningfully be a Metallica fan, but last year's Purpose was an impeccablly crafted shot at the sadboi jugular. Full of everything from whine-heavy acoustic jams ("Love Yourself") to psudo-introspective house jams ("What Do You Mean?"), the record was a revelation of the sadboi as pop consumer, an investment into sadboi narratology to translate it into an expansion of personal brand, Bieber's love interests acting "as a stand-in for a public that has turned on him," per Carrie Battan at the New Yorker. Either way, nothing quite says I'm sorry you're angry at my legitimate and real hurt than "You gotta go and get angry at all of my honesty...


Shawn Mendes: In Case You Thought You Were Making Right Decisions

Turns out Canada is just one bundle of tears processed daily into candy corn pop. Relative newcomer Mr. Mendes has his heart set on that crown that Drake's been holding pretty tightly. Already having made something of a career knowing how you betrayed him last summer and not being invited to your party, Mendes made his biggest splash by insinuating that you just really don't know how to pick out gentlemen. You know who can, tho, right?


Death Cab for Cutie: I Will Follow You Into My Feelings

Unlike most trends and styles, sadboi is really something that transcends genre, style or time. It's a theatrical melancholy that entire careers can be latched on, national tours embarked upon, and you could even marry the woman of your fans' dreams, for a little while. This is, of course, Ben Gibbard's happy-go-lucky crew from the pristine American Northwest. You know, Nirvana-country. While "I Will Follow You Into the Dark" is the obvious choice for the acoustic ho-down that feelings require, it's "Cath...," from 2008's forgotten blockbuster Narrow Stairs that layers a nice cake of emotions that can be funneled into your unassuming face. Is your heart (or that of someone you know) dying fast?


Fall Out Boy: Do You Remember Your Feelings Before They Got Big?

Continuing the trip down collective high school-memory lane (Gym Class Heroes! They had a hit!) we run into the somewhat recently-reunited Fall Out Boy. They weren't very good after Infinity on High, weren't they? Patrick Stump even did a whole solo thing that involved Lupe Fiasco. Do you know what was before all that? "Sugar, We're Goin Down." Am I more than you bargained for, just yet? Oh, yeah. I am.

My Chemical Romance: When The Sadboi Was All In the Hair

And while we're going back to high school (gotta put the boi in sadboi), why not just go back to those days where command of makeup and hair dye would convey everything you needed to know about respective levels of chill? And why not mix some weird zombie shit in there too? Just like the hearse you die to get in again! Are things really better if I stay? Really?

Neil Young: Frumpy Sadman Sayith

When Neil left his wife and musical collaborator of thirty-six years for an actress a solid ten years or so younger, I would like to imagine that their talk touched on Neil playing his 90s cult-ish jam, "Harvest Moon" before walking mournfully out the door. Covered by bearded generations of sadmen from Eddie Vedder to Bon Iver, it'll make the eyes water and manboi feelings flow.

Bobby D: Further Into the Classics of Sadboi Tears

Can you win a Nobel Prize for a career of sadboi troubadour-ing?. Yes, yes you can. While arguments have been made that he is poet and a voice of his generation or whatever, longtime fans will know that he's certainly the poet of women who've done you wrong and committed the hardcore moral failure of elevating your needs above them. See also: Leonard Cohen. For now, just know that you're the reason I'm a-traveling on:

Jens Lekman: The Long Suffering, Will Always Suffer

A personal favorite, occasional indie darling Mr. Lekman has a made his career playing the sadboi trapped in the body of a man, all while playing a dour indie pop that splits all the differences imaginable between The Smiths and Belle and Sebastian (hella legit sadboi gangs in their own right) and plays them over mid-2000s electro-indie samples. Brilliant! Like Drake, Lekman can write his feeling on his sleeve with sharpie markers, i.e. 2007's album-opening "And I Remember Every Kiss." His masterpiece in sadboi dramatics, however, is early single "Maple Leaves" --a song where he riffs on mishearing a girlfriend tell him their relationship is "make believe" as the titular "maple leaves." Sad!


Check Out These Sadboi tunes n' more on Spotify: