Ali Vegas is nicknamed the “Prince of New York” for good reason, he’s one of the shining stars of the freestyle scene and mixtape circuit.

Known as a champion battle rapper and expert off the top spitter, Ali has been rapping since age 6 and first gained attention when he appeared on the In Too Deep soundtrack as a teen. In 2006 Ali Vegas signed to NBA player Lamar Odom’s label, Rich Soil Entertainment where he has worked with producers ranging from J Nice to Midi Mafia. A steady slew of mixtapes helped cement his rep, including the much heralded The Rebirth of a Prince and Leader of The New School. This summer Ali will release Generation Gap 2: The Prequel, which features guest spots from Nas, AZ, Styles, Akon and production from DJ Premier, L.E.S, Scott Storch, Cool & Dre, and more.

So Freestyle 101 was stoked to get Ali in the booth at Play Studios in New York and watch him do his thang over a slinky Messiaz beat. And believe you me, this kid can freestyle. How do we know it’s really off the top? Well, for one thing he throws in tons of videogame references, which you don’t normally hear in his street-laced rhymes. Also Director of Photography Joe Lynch (director of Wrong Turn 2, by the way…see it now!) and I were joking around with him before we started rolling, daring him to work ridiculous terms like “alligator taint” and “yak balls” into his rhyme and he did! We nearly fell over laughing.

The kid is good. Real good. Real, real good. He makes it look so easy and raps with a smile across his face, a nice change of pace from the mean muggin’ game face most MCs display. Plus, in his interview he chats about how being sober helps keep his rhyme skills sharp, something most other rappers cannot attest to.