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Rap and show tunes don’t make the most obvious of bedfellows. Fans of, say, Eric B & Rakim seem to have little in common with those of Rodgers and Hammerstein — and vice versa. But the overwhelming success of the musical Hamilton seems to be putting such skepticism to rest. Lin-Manuel Miranda’s dramatization of the Founding Father’s life, vividly performed by a cast of color and anchored by music that skillfully incorporates hip-hop traditions, is redefining the way culture at large perceives the music of Broadway. But you have to wonder, is the feeling mutual? Would an audience of rap-heads enjoy the over-accentuated, maybe even slightly cheesy hip-hop of Hamilton as readily as its patrons on the Great White Way? To gain some perspective on the matter, Vulture caught up with Talib Kweli — days after he saw the production — who, in addition to being a highly respected 20-year rap vet, also has what could be considered a little bit of a background in acting and theater. (His father, Perry Greene, was an actor, and while in boarding school Kweli wrote a play in which his then-classmate James Van Der Beek was a star.)

“You’re not at a hip-hop club, you don’t have loud speakers, a DJ is not scratching, Eminem is not performing: It’s not that, and it’s not pretending to be that,” Kweli says. “It’s a musical that’s greatly influenced by hip-hop, and the hip-hop influence on it is wonderful.”

According to Kweli, Hamilton is a tribute to rap’s strength and malleability — its tendency to fall back on itself while also figuring out new ways to evolve. The production is also the first example of a successful Broadway show to openly embrace the ways in which musical theater and rap overlap, with characters like Washington and Jefferson, played by Christopher Jackson and Daveed Diggs, respectively, delivering plot points through complicated rhyme schemes. The technique is one Kweli has seen on Broadway before, “it just wasn’t called rapping.” Hamilton also emphasizes the ways in which both rap and musical theater are centered on linear narrative structures, but its biggest asset, says Kweli, is its cast, which includes actors well versed in both traditional Broadway and hip-hop culture.

“The guy who plays Jefferson, as soon he came onstage and did a couple of bars, I was like, ‘That’s an MC. That’s not a traditional Broadway dude. That’s a guy who raps and was put in this play because he raps.’” On the other hand, Kweli remembers seeing Jackson in Holler If Ya Hear Me, the musical based on Tupac’s catalogue, and thinking, “Here’s a guy who is clearly, clearly classically trained in Broadway, and he’s bringing it all. He’s singing songs, but he’s also rapping proficiently. With him, I couldn’t tell whether he grew up rapping or if he had to learn it to do these plays, but either way, I could tell he’s in touch with hip-hop culture.” (Holler If Ya Hear Me closed last year, after only six weeks on Broadway; Kweli says its untimely end had more to do with poor marketing than the show’s marriage of musical theater and rap.)

That ambiguity — are these MCs, or are these musical-theater actors? — is a big part of what makes Hamilton “revolutionary” in Kweli’s mind: The show becomes relatable to both audiences. But just in case there are skeptics on the rap side who aren’t convinced it’s possible to love Albert Finney and Carol Burnett as much as Nas and Wu-Tang, we asked Kweli to analyze a few key tracks from the Hamilton cast recording and to illustrate what makes them appealing from a professional MC’s perspective. Think about it like this: “We all grew up with Annie,” Kweli says, “and ‘Hard Knock Life,’” and we all saw how Jay Z transformed that Broadway staple.

“Alexander Hamilton”

“My heart swelled with pride after I heard this song, because I was like, ‘This right here is hip-hop.’ Hip-hop has no boundaries and no limits, and Lin-Manuel and his crew are proving it. All the songs are so well written. After that first round of applause [after ‘Alexander Hamilton’ is performed], the first thought that went through my head was, Wow, that’s the first song, and it was that good? Like, okay, if every song is that good, this is about to be a very powerful piece of art.”

“My Shot”

“When this song came on, it made me think immediately of 8 Mile, Eminem, ‘Lose Yourself.’ The sentiment of this song is exactly the same: You have one chance, one chance only, to make your mark in this society, and here’s your platform, your opportunity. For Eminem, it was a rap battle. This whole play revolves around people taking their shot, leaving their mark in history, Aaron Burr and Hamilton’s different ideas on how you go about doing that. The director of 8 Mile, Curtis Hanson, saw visuals in Eminem’s music; I think a similar thing happened when Lin-Manuel read Ron Chernow’s Hamilton.”



“Washington on Your Side”

“When I first heard this song, I thought, I want to know who wrote these lyrics. The rhyme scheme and what he’s saying is very impressive. It’s similar to Macklemore in terms of the fact that they’re enunciating their words clearly and telling stories. When Macklemore blew up, one of the first things he did was take me on tour, so he’s somebody I have a lot of respect for, whether people understand the reason behind his style or not. Anyway, they’re accentuating their words, but they’re doing that because it’s a play and people have to hear them. For me, it’s like when you watch a sitcom from the ‘70s and everyone’s overacting — dramatic and loud — because they were doing it in front of a live studio audience. There was no laugh track. These were people who were coming from the stage who were now on the screen. That’s what happens when you take something that belongs on the stage off the stage. It doesn’t have the same power. I don’t think you’re able to capture a Broadway sound. I’m not one of these people who listens to a Broadway soundtrack if I’m not at the show because those songs are written and designed to be seen. You have to take that into account when you’re listening to these songs, but as a 20-year veteran of hip-hop, I was highly impressed.”

“The Reynolds Pamphlet”

“The show definitely comes from the type of hip-hop that’s based on spoken word and poetry, the hip-hop that I grew up on — the hip-hop of the late ‘80s and early ‘90s. It has that rhythm, style, and tradition. That’s definitely what Lin-Manuel as an artist is inspired by. But I definitely think he’s a hip-hop liberal, meaning that he’s not stuffy or fogyish about his hip-hop. Even though he might like hip-hop from the early ‘90s, he understands that hip-hop changed, and you see that growth in the songs. I’m guessing because Hamilton was born in the Caribbean, there was a lot of reggae and Caribbean rhythm, especially with Burr’s character. So it’s not just hip-hop, and that’s what’s great about it. There’s a lot of rapping, but there’s a lot of traditional Broadway music. Pop songs, reggae songs, ballads. There were newer styles of hip-hop, too. ‘The Reynolds Pamphlet,’ for example, is trap rap. They’re doing straight-ahead trap on Broadway; they were even doing the dances that people do when they listen to trap music in the club. They definitely made sure to incorporate different styles of hip-hop rather than keep it boom-bap.”

“Cabinet Battle #1” and “#2”/”Burn”/”I Know Him”

“The cabinet battle is one of the cases of brilliance in the show, definitely. But when [Phillipa Soo] sang ‘Burn,’ the song about how Hamilton wrote these letters and built these cathedrals out of words, and the king of England, his song [’I Know Him’], I couldn’t get that song out of my head for days. Those songs to me are more impressive than the rapping, because I know they can rap, but not only can they rap, they can also do the straight-ahead Great White Way shit better than Broadway people. That to me is showing the real, true skill set here.”