ItsTheReal Turned A Hip-Hop Comedy Sketch Show Into A Full Blown Rap Project

Jeff and Eric Rosenthal are a quirky duo of Jewish white guys (brothers, but not twins) who are two emerging voices in hip-hop that you should get familiar with. If you don’t already know them, here’s a brief primer: They started out at their parents’ house in Harrison, New York, making absolutely hilarious videos skewering various aspects of hip-hop culture and rap music; now, they’re full-fledged stars in their own right.

ItsTheReal demonstrated their love for hip-hop by poking fun at both the most famous, and the most obscure references they could find, with sketches like “My Dog Earl,” which imagines an ’80s sitcom featuring DMX and Scott Storch as roommates (inspired by the former hiding out at the latter’s mansion while on the run from drug and animal cruelty charges in 2008), “If It Was All So Bey-Z” which lampooned the complicated web of late-’90s/early-’00s rap beef, and “Ghostwriters On Strike” which theorized the outcome of rap’s myriad ghostwriters unionizing.

The videos are screamingly funny still, and eventually caught the eyes of several of the entertainers they spent so much time teasing (cough, Joe Budden); rather than strike back on wax or in the streets, many of the sketches’ targets joined in the fun, playing themselves in ironic or hyperbolic situations, like the time hardcore battle rappers Slaughterhouse reorganized into a ‘90s-style smooth-talking R&B boy band.

When they managed to transition from sketch comedy to interviewing rappers at festivals for MTV, it seemed clear that the brothers were destined for greatness, however cliche that sounds. But even I was floored in 2013 when they swerved left into seriously making their own rap music, with the aptly-titled Urbane Outfitters, Vol. 1 mixtape; it skewed funny, but was actually pretty good. They showed a knack for wordplay and beat selection, but the project was taken over the top by guest appearances from rap luminaries like Freeway, Maino, and Bun B, just a few names ItsTheReal’s massive rap Rolodex has accumulated over the past decade.

They didn’t stop there, changing lanes yet again with their 2015 podcast entitled A Waste Of Time With ItsTheReal, where they’ve profiled and interviewed both artists like D.R.A.M., Kyle, Cardi B, and Killer Mike, among many other marquee names, along with behind-the-scenes industry power movers like Angela Yee, Sickamore, Peter Rosenberg, Kim Osorio, and Lenny S. The show has become so popular they decided to take the show live to New York’s Highline Ballroom on July 26th, staging a Roc-a-Fella Records reunion with Chaka Pilgrim, Emory Jones, Just Blaze, Young Guru, and Freeway.

Then, instead of resting on their laurels, ten years deep in the game, they released Teddy Bear Fresh, their debut album, in May of this year. The album features Michael Christmas, Smoke DZA, and Curren$y, and along with A Waste Of Time, is one of the many, many reasons hip-hop fans should get to know this New York-based multi-hyphenate duo. I recently spoke with the brothers to help highlight them as emerging voices in the genre, read our conversation below.

How did you come up with ItsTheReal as brand, and what made you want to do hip-hop sketch comedy of all things?

Eric: Ten years ago we came up with an idea to do what would have been a TV show. It would incorporate sketch comedy and live musical aspects and interviews, and we had zero experience in doing any of those things. We were very good at knocking down doors and getting into meetings and getting past the gatekeepers, and when those meetings were going really well they said they were interested in what we had to say, but didn’t know how it could make money, we said, ‘Well, we’ll do it ourselves.’ We decided to do the one thing that we could do on our own, which was sketch comedy, because we had a camera and Final Cut Pro and friends who would act in our ideas and time on our hands, and we just set forth to do something in our own voice, in our own point of view, in our own lane.

So were you guys already friends with all these rappers?

Jeff: Oh no, we didn’t know anybody. Eric had worked with Kanye very early on, but we didn’t know anybody. The first person that reached out was Bun B, a few months into doing videos every week. From then on, that’s when we started getting people reaching out, but starting out we didn’t have any contacts.

Eric: We started out when we were living in our parents’ house 30 minutes north of New York City. We were not out at the club every night, or making rounds at the labels, or going to listening parties. We were two guys who just loved it from afar. Maybe two months after we started doing videos we moved to the city, and we did start going out, showing our faces, getting to know people, and with that and that we were doing things at a high quality and a consistent pace, we became known.

So you found success with sketch comedy and on MTV as hosts, what made you want to transition into being actual artists yourselves?

Eric: We’ve been rapping since we were in high school. We were rapping about our experience, and inside jokes with friends. The group we were in was the Purchase Street Sweepers because that was the street we grew up on and we loved DJ Kay Slay. We talked about what we knew. It wasn’t something we envisioned as a career move, it was just fun for us. We could expand our wordplay, expand our love for music, and we only started doing it on a professional level when we did a video lamenting the seeming demise of Kanye West’s career after the Taylor Swift situation. The video was called “They Reminisce Over Ye” and it caught the ear of some execs at Atlantic records, who encouraged us to do more of that. That’s when we started to do a little more.

You went from music to doing a podcast. How did you pull that together, and how do you juggle those responsibilities?

Jeff: In 2010, we did our first podcast, but we felt like we were very early on the curve. There wasn’t really an audience for it at that time. The only one that was around before us was Juan Epstein. So more recently, we started doing this podcast, and at first it was just a good way to keep our name out there, because we were working on the TV show and this would be a good way to keep in touch with the community that birthed us. It’s grown into this whole other thing, where people really look to us to discover acts they’re not familiar with or people who are big behind the scenes. People are like, ‘Yo, this helps me get to and from work every day.’

Eric: The more episodes we do, the more time we put in, the better we’ve gotten. Our stuff has been received by more people, the audience has really rocketed, and we’ve found our niche. We’ve gone more into the industry side of things; this is a chance for us to put people on who normally don’t get the exposure.

Jeff: When we started off, we wanted it to be more comedy-based, but as it’s gone on, we found a lot of people find inspiration from our podcast.

Eric: I think we found a good balance with the podcast, to be able to do different things and be accepted in all these worlds. It’s a good platform for us to promote live shows or our album, and other ventures that our co-workers and friends are putting on. It’s become a hub for people to find us and know about the other things we’re doing.

You guys are the ultimate curators and influencers; the artists that you pick and the industry people you profile get a lot of shine from you. What does that mean to you?

Jeff: It’s tough to bring over losers to your apartment and talk to them for an hour. We just pick interesting people, who live interesting lives, who don’t get the shine that they should. We actually had a friend pass away (recently) and we wished we could have told his story.

Eric: Everyone’s got their lane, because if you don’t do something specific you might get lost. We’ve been able to establish our own lane with the industry folks who talk about their careers and their journeys to this point. It ends up being a living document, and we’re very proud of that. We appreciate the fact that we can put people onto other people and give inspiration. It’s amazing.

Part of it is longevity in the game, part of it is the ability to coax stories that weren’t on the top of someone’s head out. We’re pleased to be more relevant than ever ten years in.

You look like outsiders to hip-hop, and there are other white performers in the genre who really seem to take it seriously but have gotten into trouble for appropriation, etc. How do you guys avoid that pitfall?

Jeff: I’ll say this. We grew up in a family where our mom would tell us about the three kids in Scarsdale who flew down to help out with the Civil Rights Movement and wound up getting killed. Our upbringing plays a huge part in making who we are. We’re very careful, respectful… we don’t cross lines. Everything about this is hard. I don’t know how anybody does anything. It doesn’t mean everything has to be celebrated — ‘everybody gets a gold star for effort’ — but you do have to respect people for putting themselves out there.

Eric: We just understand who we are, and we understand what this culture is about, and what this lifestyle is built upon, and we never wanted to do anything to tear it down or disrespect it. We’re two Jewish kids, and if you put a still of our faces on a Youtube video, you could surely make a judgement on us. But if you watch any of our videos, if you listen to our interviews, listen to our music, push play on anything we’ve done, if you ask anyone about us, you will see the truth about us.

Jeff: If we were more cavalier and didn’t care so much, we could be more “successful.” A lot of people have been successful by embracing controversy. Now, it’s not crazy for white kids to like rap, and drink water from Aqua Hydrate, which is a P. Diddy product. We grew up at a time where you did have to prove yourself and be respectful. Maybe we’re a little old school in that respect.