Developing a cult following with his niche brand of “herb” friendly lyrics, it seems only right that Wiz Khalifa would eventually reach mainstream success.

The Pittsburg native released his first album Show and Prove in 2006, after joining the Rostrum Records roster. Harboring a classic Hip-Hop vibe, the opus got the attention of Rolling Stone Magazine, who dubbed the young Wiz an “artist to watch.”

A brief stint with Warner Brothers Records was the product of several projects, including Grow Season, Prince of the City 2, Star Power and Flight School. Despite a number of appearances and collaborations, his debut album with the label never saw the light of day.

Parting ways with Warner, Wiz continued working with Rostrum and quickly became a trailblazer for the indie Hip-Hop scene.  Circa 2009, Wiz joined New Orleans MC Curren$y to release their joint effort How To Fly. Khalifa stepped into new territory with this release; more melodic beats and even a bit of “singing,” if you call it that.

The rapper quickly made his way onto everyone’s watch list, scoring a spot on XXL’s coveted Freshman List, and The Source’s Rookie of the Year. Somewhere between releasing his Kush and Orange Juice mixtape and selling out shows with Yelawolf, Wiz’s career creeped to new heights.

Even a little marijuana trafficking couldn’t stop the rising star, who crossed over to the mainstream when he released his viral single “Black and Yellow” under Rostrum/Atlantic.

Releasing his Atlantic debut Rolling Papers, Wiz abandoned his underground roots for a more label-friendly style of sing-songy rap. He may have lost some fans along the way with his cross-genre transformation and all, but what’s more important is the way he was able to cultivate a loyal fan base organically, while rising to mainstream fame.


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