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He can go from a suck-a-dick verse ("When rappers start rappin' over indie shit/Just remember I was first to hit this shit") to a child just trying to fit in ("I coulda been a tragedy/That's why these fake niggas who call me 'pussy' are 'mad' at me/'Cause they ain't have the smarts or the heart/Ain't you read the fuckin' book, Things Fall Apart?") to a wailing, hopeless, and hurting romantic ("I don't wanna be alone/'Cause you know/Somewhere inside/I cannot find/The feeling I got from you").
It's a bit schizophrenic—but much like how Glover doesn't separate his TV persona from his Web persona, he doesn't care to compartmentalize. For this, he has his detractors. Satirical cultural critic Hipster Runoff teased him by wondering if the "blipster" is too eager to "make it as a buzz band" (in a review of a Voice review). The AV Club picked apart his album Culdesac as "a collection of good ideas that still need to be finessed into a strong statement," attacking the wild range of emotions and personality from song to song. But that's exactly the point. "Fuck Rap Cool," the hashtag Glover often adds to his Tweets, is the one tattoo to be etched on him at this stage in his career.
In his raps, he makes frequent mention of his manhood. His propensity for thick women, particularly of Asian descent, is well-documented, and on one track he gives a shout-out to e.e. cummings—you can fill in the rest. But in between, he's rapping about alienation, trying to fit in, getting girls to like him. Nerdy emo with a fro. Name-dropping Greedo and Inspector Gadget one minute, then laying something like, "Whiskey-sippin'/Wanna drink the whole bottle/But these smart middle-class black kids need a role model" the next.
"So many black kids Tweeted me about that line," says Glover. "This is the first time in history we are able to talk about alienation and nerd things. Black kids do like white stuff. Arcade Fire were at the top of iTunes—it ain't all white people listening to them." He represents a new archetype of entertainer—a black nerd who can like white stuff. Not a black nerd in the over-the-top Steve Urkel or Dwayne Wayne sense, but a regular black guy who likes the same stuff white people like—but just happens to be more talented than you.
The black middle-class kid is a real thing. Earlier that night, before heading to Pianos, around the table of Boka Bon Chon with his two biological siblings, brother Stephen and sister Brianne, and high school friend Lauren, the conversation turns to race—who can say the N-word and who can't. "He was voiced by a black dude," he wonders out loud. "So is it OK for Darth Vader to say the N-word?" He quickly Tweets the question out to the world.
"During the whole Spider-Man thing, the only thing that ever hurt my feelings was this one comment. The guy said, 'Look, I love you. I think you're great. But let's be honest: There are no black kids like Peter Parker,' " he says, shaking his head. "There are!"
And Glover will let us all in on a little secret: His first taste of rap wasn't NWA. Or Run-D.M.C. Or even Eminem. No, his first taste of rap was guys like Fred Durst.
"They say there's no place in hip-hop if you're in the suburbs," he says. "Kanye is a suburban kid. The struggle is finding your place."
While in his senior year at NYU, Glover got an e-mail from David Miner with the message "I heard you write." Miner had gotten his name from Tina Fey, who got it from Amy Poehler, who got it from his teacher at Upright Citizens Brigade.
They asked him for some writing samples. He sent the spec script he wrote for The Simpsons, along with one for Everybody Hates Chris, along with some sketches he had written.
Miner and 30 Rock co-creator Fey liked them. Not yet having graduated from NYU, he was now a writer on 30 Rock.
While Glover is often cited as a driving force behind a lot of Tracy Morgan's best lines, his first joke to make it on the show was a punchline for Kenneth, the white hayseed NBC page—whom he says he actually most identifies with, if anything because of the fact that both (fictional white clueless guy and real black nerdy guy) hail from the same town: Stone Mountain, Georgia.
Eager to perform as well as write, Glover started doing stand-up. In the beginning, he took advice from Tracy Morgan: "Talk about penises—dudes loves that." And later, advice from Chris Rock: "What the hell was that!? It looked like you went onstage and said 'dick' for 45 minutes."
Meanwhile, he continued to mix beats and rap and, with his Derrick partners, produced and starred in the Encyclopedia Brown send-up indie film Mystery Team. But he wanted more. In 2008, he auditioned to play Obama as a cast member on Saturday Night Live, but didn't get the part. At the end of the third season of 30 Rock, he told Fey he wanted out. She gave him her blessing, and he left the most stable and secure thing he had, packed up the Derrick team in a two-car caravan, and headed to L.A., moving to Beverly Hills Adjacent, in an apartment building that also housed a brothel and a dentist's office.