Rapper Riff Raff is getting to be as rich and famous as he jokes about being
Rapper Riff Raff is getting to be as rich and famous as he jokes about being Credit: Chelsey Croucher

Hang out with enough professional-grade rappers and you’ll notice a number of shared traits that differentiate them from civilians—that they’re capable of superhuman feats of lateness, for instance, and can amass collections of hangers-on as impenetrably dense as the entourages of A-list Hollywood actors. You’ll also find that they tend to be ridiculously funny.

The relationship between hip-hop and comedy runs deep—take the beats out of the picture, and both boil down to applying wit and wordplay to observations of the human condition. (Blowfly, one of many claimants to the title “first rapper ever,” was an R&B songwriter with a side career making incredibly profane comedy records.) Boasts and insults—basically the backbone of rap—are far more effective when they come with punch lines. And like most art forms that have arisen from African-American culture (think about early blues and jazz, or the giddily filthy lyrics on old hokum 78s), rap blurs the line between the comic and the serious.

Because hip-hop’s takeover of mainstream pop culture began in the 90s, when gangsta rappers and academia-steeped conscious rappers combined forces to ensure that there wasn’t too much laughing going on, in the popular imagination the genre is often associated with unflinching, straight-faced toughness. This image is so deeply ingrained in the hive mind, in fact, that it’s easy to forget that the first rappers to find multimillion-dollar mainstream success—complete with a lucrative, long-running Swatch endorsement—were the Fat Boys.

In case you needed a refresher, this month the trio’s self-titled 1984 debut LP got the deluxe re­issue treatment from Tin Pan Apple, the label founded by their ambitious Swedish-born manager, Charlie Stettler. The rerelease should also remind present-day listeners that the Fat Boys deserved their fame. Because they weren’t above treading novelty-act territory (they’d probably gotten famous for exactly that reason), the years since the Fat Boys’ 1991 breakup have been unkind to the group. Their outsize comic personas—the alarmingly huge restaurant tabs, the way they’d mug goofily for seemingly any camera pointed at them, their roles in the 1987 movie Disorderlies—have stuck in the public’s memory far better then their prodigious musical talents.

Fat Boys

Listen past the high jinks on Fat Boys, though (the reissued CD comes in a tiny pizza box), and you’ll hear the group for what they were: ambassadors for a radically avant-garde music scene who were willing to do whatever it took to bring a highly skeptical mainstream around to their art, up to and including playing up their chubbiness, rapping about pizza, and covering golden oldies. There’s a good reason the Fat Boys—then called the Disco 3—were the surprise walk-on winners of the 1983 talent competition that landed them their deal with Stettler. They rapped as hard or harder than any of their early-80s NYC contemporaries, and one reason their shtick landed as well as it did was that these undeniably hefty men so often astonished potential fans when it turned out that verbally—or, in the case of the late Darren “the Human Beat Box” Robinson, nonverbally—they were as quick and nimble as little deer.

It’s impossible to ignore the comedy, though, and you shouldn’t try. There’s something beautiful about the moment in “Jail House Rap“—a brooding, chilly crime drama produced by Kurtis Blow—when we learn that the hardened street thugs the Fat Boys are playing were all sent upstate for pizza-related crimes.

It also helps to keep the Fat Boys’ balance of lowbrow humor and ruthless proficiency in mind when you’re listening to Texas-born rapper Riff Raff. A couple years ago, all anybody could’ve known him for was a brief 2009 stint on the fantastically trashy MTV reality show From G’s to Gents. But over the past year the enigmatic performer (who won’t reveal his real name or his age, and who often does interviews as “Jody Highroller,” a persona with a quasi-­British accent) has leapt from obscurity to ubiquity, at least among a certain set of Tumblr-addicted rap fans and tastemakers.

Like the Fat Boys, Riff Raff is shameless when it comes to publicity. After MTV, BET, and the website WorldStar­HipHop covered him, he had their logos tattooed on his body. His look combines long, flowing blond hair with grills, a tightly sculpted beard, and rainbow-­mirrored sunglasses similar to Oakley Blades, a model much coveted by redneck teenagers in the late 80s. Gawker calls him “The Most Viral Human Being in Music.” James Franco is playing a character based on him in Harmony Korine’s next film, Spring Breakers—Korine first tried casting Riff Raff himself, but the rapper didn’t reply to his e-mail in time.

Much of this appreciation is obviously ironic, and sometimes it feels like Riff Raff is daring his audience to take him seriously—why else would he form a group called Three Loco with prankster Andy Milonakis and former MTV VJ Simon Rex? But his mixtape Summer of Surf, which came out earlier this month, makes a convincing case that we should. (In what I can’t believe is a coincidence, it starts with a sample of the Surfaris’ “Wipe Out”—which the Fat Boys famously covered.) Culled mostly from Riff Raff’s unpredictable Internet output, Summer is his first official collection (earlier compilations were assembled by fans), and it’s incessantly hilarious. Riff Raff’s raps, all of them apparently freestyled, are nonstop non sequiturs, dozens upon dozens of punch lines to a single joke—whose setup is Riff Raff, his image, and his persona. The lines “Camp counselor, living in the lap of lux / Double cheese deluxe / In the penguin tux” don’t make much sense, but they do something better, evoking a surreal sort of high-class living that it’s easy to imagine Riff Raff enjoying.

The aforementioned line comes from the best Riff Raff track so far, “Cuz My Gear,” on which he collaborates with rapidly ascendant Chicago rapper Chief Keef. When Riff Raff isn’t making songs with comedians and other Internet rappers whose legitimacy is frequently questioned (Kitty Pryde, Kreayshawn sidekick Lil Debbie), he’s making them with straight-faced, serious acts, which is far funnier. The first minute of “Gear” sets the scene with ominously booming pianos, a twitchy trap beat, and a typically catchy chorus from Keef—and then Riff Raff bursts into the song like the Kool-Aid Man, except this time the Kool-Aid Man is on something and he’s crashing a gangbanger’s funeral. The effect is even more jarring on “You Never Know,” a featherweight piece of emo-tinged electro-pop by an otherwise unknown Los Angeles group called Bright Matter. Riff Raff appears in the video, but his personal brand of chaos magick is so effective that even while you watch footage of him and the band walking through LA and getting their hair blown around in slow motion, you can have a hard time believing that any of it actually happened.

Riff Raff recently signed a deal with Diplo’s label, Mad Decent, which just issued Rap Game Bon Jovi, an iTunes album largely made up of old cuts like “Deion Sandals”; on August 7 the imprint will put out a free “best of” mixtape called Birth of an Icon via livemixtapes.com. In his Twitter bio, Riff Raff says the deal’s worth $3 million. (His Twitter bio also describes him as the “#1 sleep walking booty grabber in Sweden” and a “Grammy award winning gynecologist.”) I’m not sure that you say that Diplo is in on the joke, because I’m not sure that anyone but Riff Raff is totally clear on what the joke even is. Likewise I don’t know whether Diplo will get Riff Raff a cameo on a single by any of the hip-hop, pop, and R&B super­stars who’ve been knocking down his door, but I hope so badly that he will. The funniest possible punch line for the Riff Raff joke would be if he actually became as rich and famous as he already is in his raps.