The Tragically Unhip

I’ll probably be branded a traitor for doing this. The tag “hipster rap” is anathema to most of the artists who have been branded with it. These people would like you to know that what they make is simply hip hop, not hipster rap or nerdo rap or any such pigeonholing label. However, the useful thing about tags is that they allow you to promote a bunch of stuff you like that sort of shares a similar sensibility.

So here’s a hipster rap primer: a guide to a bunch of artists who wear funky clothes, like geeky, old-school things, and make music that may be rap but is definitely not from the 50 Cent/mainstream radio school of rap. I’ll admit to stretching it a little in this piece, because I’d rather include boundary-stretching rap that is a tiny bit hipster over really hipster-y stuff I can’t stand. For instance, Asher Roth is most definitely a hipster rapper, but I can’t think of one of his songs that I like, so you’ll get Wale (who’s harder to put in the genre) instead. Download the playlist here, and enjoy.

10. Keep Moving (ft. Fresh Daily)

Artist: Mickey Factz

Album: The Leak Vol. 2

Mickey Factz reps hard for hipster nation. From the thick, plastic frames and shiny gold sneakers, to his penchant for rapping over instrumentals from hipster favorites like Fall Out Boy, Zoot Woman, Telepopmusic, and Portishead, he’s pretty much established himself as a kid from the Bronx who really knows what’s going on downtown. Here he is with Fresh Daily over a really jazzy sample that I ought to know but don’t.

9. Roxxanne

Artist: The Knux

Album: Remind Me in 3 Days

Like their friends in Williamsburg, the Plateau, and hipster ‘hoods worldwide, hipster rappers know about dressing to stand out from the mainstream. The Knux are so colorful and preppy, they’d make both Carlton Banks and the Fresh Prince stand down. Luckily, their music also has enough dirty rock riffs and joie de vivre to get the approval of said Bel Air residents.

8. Generation Lost

Artist: B.o.B

Album: Leaders of the New Cool

B.o.B. probably shares your grandma’s opinion of most of today’s rap. He calls it crap and stands apart from it with a really weird flow and by being even more salacious than Amy Winehouse on her own tracks. He is kind of hard to peg as a hipster rapper because he isn’t working with the same aesthetic as most of this list, but he’s so left field that he’d probably go down with them in a drive-by. I like B.o.B.

7. Driving Down the Block (Low End Theory)

Artist: Kidz in the Hall

Album: The In Crowd

The Kidz in the Hall rep for those hipsters who really wish their time in Ivy League universities had never ended. UPenn graduates Double-O and Naledge reference marching bands, perform in varsity jackets (or sometimes smoking jackets) and quite obviously had a hell of a time in college. This song is pretty much the hottest thing they’ve ever put out.

6. Windows Media Player

Artist: Charles Hamilton

Album: N/A

Charles Hamilton is an intense young rapper who loves Sonic The Hedgehog and makes laid back but serious-minded rap tracks. We will not discuss his hipster credentials or lack thereof, but note that this track is built entirely off sampling the Windows OS boot-up sound and shouting out the name of his blog and various other websites. It’s a woozy, weird experience.

5. Is There Any Love (ft. Wale)

Artist: Kid Cudi

Album: A Kid Named Cudi

Kanye’s latest signee Kid Cudi just put a totally smoked out wonder of a mixtape titled A Kid Named Cudi. Blowing through your speakers from the home of the original harmonizing rappers themselves (Bone Thugz n Harmony), Cudi is all about lazy singing, lazy rapping and introspective but playful lyrics. Check out this track, then check out the mixtape.

4. C.O.L.O.U.R.S

Artist: Fonzworth Bentley

Album: Can’t Tell Me Nothing (The Official Mixtape)

I don’t think anyone has put Fonzworth Bentley under the hipster rap umbrella previously, but if the parasol fits, then you know Bentley will be under it in a sweater vest and two-tone spectators. Diddy’s former butler seemed mighty unlikely to become a serious artist, but he’s been hanging with—and presumably receiving tutelage from—Andre 3000 (the Great), putting out some low-key but promising tracks, singing and rapping about girls and all that weird shit he likes to wear. On this minimalist wonder of a track, he describes himself as being “the type of brother got a castle with a cognac river for a moat.” Awesome.

3. Ho’ is short for Honey (ft. Kid Cudi)

Artist: 88 Keys

Album: The Death of Adam

88 Keys isn’t a hipster rapper, he’s a hipster rap producer. He maintains his hipster cred by only stepping out of the house in loafers and one of 700 Polo Ralph Lauren pieces. His hysterical album, The Death of Adam, deals with the tough nature of modern love, exploring in detail such well-known elements as morning wood, restraining orders, staying up (Viagra), getting burned (STDs) and of course, MILFs. Classy.

2. The Chicago Falcon Remix (ft. the Budos Band)

Artist: Wale

Album: The Mixtape About Nothing

Wale is probably the most prime time ready of the hipster rap brigade. He’s been featured on the Roots album, made a song and video in association with Nike (the surprisingly hot “Nike Boots”), and makes conventional street bangers à la Jay-Z/T.I./whoever. If this makes you doubt his hipster cred, do note that he made an entire mixtape centered around Seinfield (The Mixtape About Nothing), is in love with Lindsay Lohan, and gives his tracks painfully self-aware titles like “The Cliché Lil’ Wayne Feature (It’s the remix baby!).”

1. Beeper (Cool Kids Remix)

Artist: The Cool Kids

Album: WEDOITRIGHT – The Cool Kids Collected & Compiled

If the Cool Kids have anything to do with it, Chicago will be remembered not only as the home of the first black president but as the place where the fresh reemerged. Emerging the most fully-formed of the new crew, Chuck English and Mikey Rocks pretty much have their sound down: a blend of spare and hollow, Neptunes-weird beats with menacing bass lines, complemented by onomatopoeic nonsense lyrics about the cool misadventures of the kids. Picking one track from these guys is really hard, as there’s a ridiculous wealth of amazing material to choose from. Check out the Bake Sale EP, the Totally Flossin’ mixtape, and the WEDOITRIGHT compilation for more.

Honourable Mention: Getting Up

Artist: Q-Tip

Album: The Renaissance

Bonus Cut: I think what the aesthetic, most of what’s considered hipster rap, leans closest to in antecedent is the native tongues collective, De La Soul, Tribe Called Quest, etc. By extension then, Q-Tip is the original hipster rapper. His latest album, The Renaissance, is one of the best of the year and totally worth listening to with some square frames on.