12 Tracks, Two And A Half Hours: Sound Of The City's Mixtape Of Long Rap Songs

Last week, the new Gorillaz track "DoYaThing" dropped. It's long—a full 13-minutes and some seconds of music, a lot of which involves Andre 3000 getting frenzied and inspired with that rapping thing he does so well. With "DoYaThing" and persistent talk about Outkast reunion rumors bedazzling up the Internet, it seems like an apt prompt to get all expansive and cobble together the world's longest rap mixtape.

But first some rules! We're imposing a ten-minute minimum threshold. In the interests of listenability, we're also nixing any freestyles (sorry Game and your "300 Bars," and Weezy and your alleged "10,000 Bars"), and we're abiding by the rule of keeping it moving so the playlist spans hip-hop's growth and doesn't just dwell in a pool of lengthy old-school rap tracks (not that doing so wouldn't result in a very fine mixtape). We're also being curmudgeonly and overlooking anything that drifts into the realm of the ridiculous, like Canibus's 45-minute "Poet Laurette Infinity"—after all, if you're making your way through an artisanal 12-course tasting menu, the last thing you want is Canibus's rancid, oversized pulled-pork sandwich tampering with the delicate balance of your seared scallops with morels in a balsamic reduction sauce. In the interests of playlist culture maximization (and further clogging up your iPod), here's the world's greatest longest 12-track rap mixtape.

(Note: Thanks to YouTube's uploading rules, some of the clips might cut off at the 10-minute mark.)

1. The Sugarhill Gang, "Rapper's Delight" (15:00)

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The Sugarhill Gang's Chic-sampling bow is also ambitious in length, clocking in at a good quarter of an hour. A fitting start to the playlist, then, although it's best to gloss over the disingenuous bits about Big Bank Hank nicking Grandmaster Caz's lyrics and the rampant rumors about the Sugarhill label's industry tactics in favor of enjoying the elongated groove. (Alt Starter: Jimmy Spicer's "Adventures Of Super Rhymes (Rap)," which runs for just as long.) Total running time: 15:00

2. K-Rob vs. Rammellzee, "Beat Bop" (10:10)

Future funk ahoy! Here William S. Burroughs's favorite Far Rockaway representer, Rammellzee, hooks up with K-Rob for an entertainingly warped ten-minute workout. Ensuring that the first pressing of the record was far too expensive for mere mortals to buy, the cover art was provided by Jean-Michel Basquiat—who was rumored to at one point have been invited to spit on the song. Total running time: 25:10

3. Too $hort, "Freaky Tales: The Saga Continues Part II" (10:24)

Too $hort is the west coast's finest practitioner of the protracted rap song. His early, cassette-only catalogue regularly boasted tracks that tailed off around the eight- or nine-minute mark, and the fan of the derogatory b-word topped the ten-minute threshold with his sequel to "Freaky Tales" (which itself was just shy of the dime mark). Dropping in 1988, the song has the Oakland vet in archetypal pimp mode and at one point boasting about how he "hit it one night in a phone booth." Kids with smart phones just can't relate. Total running time: 35:34

4. Beastie Boys, "B-Boy Bouillabaisse" (12:34)

This plate of hip-hop gumbo is the ne plus ultra of sample-based, ADHD hip-hop. As the adventure unravels, beats, tempo and tone switch up and out with gleeful abandon, while the the trio runs amok through the city—although contrary to the track's title, it's a mere hot dog that fuels the Beasties' mission. Total running time: 48:08

5. Digital Underground, "Good Thing We're Rappin'" (11:34)

Tongue-in-cheek pimping from Shock G and the gang, who take a money-makin' jaunt across the US, meet a girl named Cookie (her name rhymes with "rookie"), and wrap the whole shenanigan up with the disclaimer, "It's a good thing that I'm rapping/ If it wasn't for the rapping, I'd be mackin'." It's an apt sonic segue into the next selection from Shock's fellow west coast rapateers... Total running time: 59:42

6. Dr. Dre feat. The Lady Of Rage & The Dogg Pound, "Puffin' On Blunts And Drankin' Tanqueray" (12:00)

Tucked away on the b-side of the "Dre Day" single, the good Doctor's lengthy instructional title is nuthin' but an excuse for some of Death Row's inmates to drop freestyle-esque rhymes over an archetypal g-funk beat that includes a slightly annoying, high-pitched synth-wail. Dre himself, for what it's worth, definitely sounds somewhat enhanced (read: pissed or high) on his ad libs. Total running time: 1:11:42

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