[caption id="attachment_96969" align="aligncenter" width="600"] Hoodie Allen[/caption]

For lots of people, the title of this post will seem pretty stupid. "Of course we should be listening to Hoodie Allen!" they might say. "We've been listening to Hoodie Allen! Where the hell have you been?!?"

That's because Steven Markowitz (as his mama calls him) has been rising through the ranks of underground hip-hop for almost four years. And despite not having a manager or a record label, he's developed a dedicated fan base that sent his album All American into Billboard's Top Ten. It also looks like a Twitter campaign is going to get Hoodie on Jimmy Fallon's show. (Slate just published great article about Allen's genius for social-media promotion and his willingness to call fans after they buy his album.)

Hoodie just played a sold-out show at New York's Roseland Ballroom, a few blocks from where I live. As I was walking home last weekend  I had to navigate the enormous mob of fans with his name scrawled across their bodies and clothing.

Allen's backstory isn't your typical "raised on the rough streets" tale: He's a Wharton graduate who left a lucrative job at Google to pursue his hip-hop dreams. If you're a reasonably well-off kid who likes rap music, you won't have to perform any cultural translations to understand his music. He's from your world, and he's making hip-hop just for you.

That's not an insult: I grew up in a suburb of Chattanooga and, if I were 16-24, I'd totally be his target demographic. And it's a good thing when artists connect with communities who recognize them as part of the tribe.

When niche artists go mainstream, of course, their identity either gets diluted or gets suddenly adopted by a massive new audience of "outsiders." Gangsta rap was underground for a specific community until Dr. Dre and Snoop Dogg became global sensations and everyone was bumping like they understood Compton.

Shakira used to record provocative, thoughtful music in Spanish, but traded some cultural cred for a massive, multilingual career and a seat on The Voice.

Will that happen to Hoodie Allen? If he makes it on Fallon, will he be embraced by more and more people until he's not just a hugely successful underground story? Just look at Macklemore, another well-off white-guy rapper: Less than a year ago, he and Ryan Lewis were delighting an underground fan base and now they're everywhere. There are probably some longtime Macklemore fans who aren't thrilled with how he's reached mainstream success, but the music is just so damn good—and Macklemore's team is so damn savvy at reaching people—that there's no stopping his success.

Check out Hoodie Allen's "No Interruption," a bouncy,  hey-lady-let-me-seduce-you-with-my-quirky-cool single from All American:

That's a pretty sick chorus, right? Meanwhile, on "Cake Boy," Hoodie gets grimier:  Over a sparse beat, he drops dirty lyrics about the "fancy hos" who love him. He also mixes up his flow, rapping super fast like he's in Bone Thugs and tossing in some Cash Money-friendly shouts.

And then there's "Fame Is For Assholes," which drops references to Homeland, Ashton Kutcher, Emma Watson, and Emma Stone. If he just mentioned Mad Men, this song could be the ultimate anthem for white people.

For me, this music isn't nearly as interesting as Macklemore's, because even in his singles, Macklemore blends the goofy references with serious, vulnerable discussions about gay marriage, drug abuse, and personal demons. By contrast,  Allen is more of a weightless party dude. Still, his songs are catchy as hell and I wouldn't be surprised if one of them blows up.

Previously: Should we be listening to Gin Wigmore?

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Mark Blankenship is glad to know that Homeland has now been reference in a rap song. He tweets as @IAmBlankenship