One key component of hip-hop is punch lines, those highly rewindable metaphors, turns of phrase, or straight-up jokes that make fans’ ears stand at attention. Another important aspect is timing–staying either ahead of the beat or behind it. But punch lines and timing are also two of the main ingredients of comedy.

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Point is, hip-hop and comedy have more in common than most people understand. The boat-side boasting of The Lonely Island has been the most prominent example thus far, but perhaps the most fully realized merging of hip-hop and comedy has come from Eric and Jeff Rosenthal’s project, ItsTheReal. Where the SNL-launched Lonely Island crew is adept at making fun of hip-hop in broad strokes, few have satirized its specifics with the eye for detail, the authenticity, or the underlying reverence of the Rosenthals. If trusted news venue WorldStarHipHop is the CNN of the genre, this duo’s sketches and interviews comprise its Colbert Report. On April 1, however, the brothers are taking their biggest step away from commenting on the culture, in a move toward contributing, by releasing their first official mixtape: Urbane Outfitters.

Urbane Outfitters features the brothers rapping alongside legitimate hip-hop stars like Bun B and Freeway, as well as hip-hop-savvy comics like Hannibal Burress. Rather than Weird Al-style parody, the songs are all originals, wringing laughs out of the genre’s notorious tropes. “Girls of the Dirty South” is a typically juvenile trunk-rattler about women’s grooming habits, and “Sun’s Out, Guns Out” is a tribute to forearms instead of firearms. DJ Drama Lending an invaluable stamp of credibility to the project is fiercely respected mixtape curator DJ Drama (no joke), who plays host and presides over the proceedings. Drama and ItsTheReal had been in touch over the years, forming a mutual admiration society, and eventually, it was the DJ who suggested teaming up. He took his role in the project seriously, too. “He would call us three times in a night with different ideas. He understands where he can be made fun of and where he can play with his image,” Eric says. Drama’s collaboration also guarantees a certain level of exposure, given his status as an ambassador from the world of true street hip-hop. “For us, it’s probably the biggest co-sign we can get for a mixtape,” Eric adds. Most of the time, when hip-hop is made fun of, it’s done by comedians who seem to have a slightly more than cursory knowledge of the music at best. The Rosenthals, however, have encyclopedic knowledge of hip-hop and comedy and a lifelong admiration for both. In 2007, they began channeling their fandom into sketches under the name, ItsTheReal.

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“We were just making these videos for family and friends, and never thought it would actually grow into something as tangible as it has,” Jeff says. The duo’s first video was called Deconstructing Biggie. In it, the brothers use a Notorious B.I.G. line (“You’re mad because my style you’re admiring, don’t be mad–UPS is hiring.”) as foundation for a fictional feud between postal services, with DHL and FedEx on one side and UPS on the other. It got 40,000 views overnight. A long series of videos followed, premiering on the brothers’ website every Monday for three and a half years. Sketches like Lloyd Banks Retirement Party lobbed sharp darts at precise targets for a niche audience. You had to be an aficionado to know why it would be funny for 50 Cent-associate Banks to be “retiring” from hip-hop in 2007 and not, say, the previous year. Hip-hop had seemingly found some comedic cultural critics capable of responding in real time. “It’s an ever-evolving genre, and I think that’s what’s maintained our interest throughout our whole lives,” Eric says. “It’s easy to make the same decades-old jokes that people make, like, ‘Look at everybody wearing gold in their teeth and putting big tires on their cars.’ But I think that we’re finding fresher material than most people.” The weekly sketches ended up forming the first of four phases for ItsTheReal. The second phase involved a regular podcast with kindred spirit Jensen Karp, a former rapper who once had a million-dollar record deal under the unfortunate name Hot Karl. The Hype Men podcast went on for a full year before amicably ending. By that point, ItsTheReal had been embraced by the hip-hop community.

Southern rap demigod Bun B was the first MC to get in touch with the Rosenthals. He called them up without any prologue and professed his appreciation. The progressive Bun B proved to be a pioneer with Its the Real, setting a precedent for other rappers who wanted to get involved. Soon, the duo were contacted by people like the members of Slaughterhouse, who volunteered to be in a video likening the supergroup to a boyband.

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“It was very out of character for these guys, because nobody really gives them the opportunity to be funny,” Eric says. “It’s not always about us. We’re willing to be clowns, but we want the artist to look better next to us and we want them to show their full personality.” After a while, the brothers started getting approached by both media outlets and hip-hop publicists to appear in videos with some of the rappers they’d long appreciated from afar. A joke hashtag the Rosenthals created on Twitter about rapper Ace Hood got so popular, the Def Jam publicists conceded that the duo had done more for their client than they had. Thus began the third phase of ItsTheReal, a transition from SNL-style sketches to short-form comedic interviews for venues like MTV and Bonnaroo. “People who go on press runs probably get so used to the same questions and are so bored with the same sort of song and dance, we thought we’d provide something so different that they’d be excited to try it,” says Jeff. In the interviews with hip-hop artists, who run the gauntlet from Ludacris to Danny Brown, the Rosenthals affect the bravado of their subjects in a deadpan style that never acknowledges or questions their nerdy, Jewish appearance. At the top of each interview, they growl their given names at the camera, followed by a stream of ridiculous nicknames (e.g. “Ja Rules of Engagement”) and “brrap-brrap” gun noises. The interviews skirt the line between hilarious, obnoxious, and informative, and everyone involved seems to be having fun. Over the past couple years, however, the Rosenthals have quietly been prepping the fourth phase of ItsTheReal. After Kanye West’s infamous interruption of Taylor Swift’s VMA acceptance speech in 2009, the brothers made their first rap video. “They Reminisce Over ‘Ye” is basically a tongue-in-cheek latter day version of Puff Daddy’s “I’ll be Missing You,” but instead of mourning a recently deceased Biggie Smalls, the two lament the downfall of Kanye’s career.

They followed this video on the eve of the 2010 election, with a political rap called “My Girl’s a Republican.” The elaborate single-take video took a week of planning, but when it came out, it was picked up by news sources like the Huffington Post and the Washington Post. The Tea Party even formally came out against it. These songs ultimately only serve as appetizers, though, for the main course that is Urbane Outfitters, the two-volume mixtape ItsTheReal is releasing.

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“We want to take what has been defined as a mixtape and just tweak it slightly like what we’ve done with our sketches and interviews,” Eric says. The second installment of the mixtape is due out in June, shortly before ItsTheReal take the stage for a set at Bonnaroo—the second year in a row they’ll be performing at the festival. The first volume’s release date took some soul-searching, though. While Memorial Day weekend seemed like a solid option–a chance to deploy the darkly funny fake catch phrase “We’re killin’ everybody out there”–releasing on April Fools’ Day ultimately made more thematic sense. The only problem is that now people might mistake it for a joke.