There's a good chance the only reason you've ever heard a Wiz Khalifa verse is because you loved Girl Talk's "Don't Stop," but here's an explanation about why there's a very real chance he's about to rule the pop charts.
In order to make this a chronological (chronic-logical?) examination of Wiz Khalifa, the first video that has to be discussed is his first video for "Youngin' on his Grind." Besides self-identifying as a young rapper (sometimes even calling himself "Young Wiz"), this video intersperses scenes of Young Wiz in the studio, rewriting lyrics and recording. The production is kind of annoying and the chorus is pretty bad but the rapping is pretty solid from the get-go.
Youngin' on his Grind
Click to viewAlthough that was his first video, things didn't really start to pick up for Khalifa until he released the video for "Say Yeah." This was was definitely his first important single; important enough to pop up in the aforementioned Girl Talk song. When you watch the video there's a huge disconnect between the song's content and the video itself. Sure, he's getting money and he's in clubs but that doesn't quite match up with the cartoon backgrounds.
Click to viewHe still looks really young, too. Perhaps Warner Brothers had a hard time figuring out how to market him—he looks young but he raps like the twenty something he is. That should have made him more marketable, but rap is probably about 50% skills and 60% confidence and follow-through. Speculation aside, his next video was for a song called "This Plane." The difference between the two videos is pretty tangible: there's tour footage and Wiz appears to have grown into himself. The touring aspect seems to imply that he has figured out what's working for him. He's even singing on this song. Be careful with this video at work, though: this version's lyrics are uncensored.
After that comes the somewhat legendary Kush and Orange Juice mixtape. Some new to Khalifa were thrown off—there's a lot of hype around this guy but this is an hour-long album about how he likes to wake and bake. Yet at the same time, this mixtape got him a deal at Atlantic Records. One of the songs was dubbed "Mezmorized" and got a video.
Click to viewAnother song of the album got a video, too, but instead of a visit to a mall, Khalifa filmed a party. You could argue that both of those two settings are still somewhat immature, high school elements, but the video itself has an abundance of people in it who are older than high school kids doing what we hope no high school kids do. However, Khalifa did corner himself in the music video department when he released an entire mixtape about getting high—there's only so many avenues you can explore without getting your video banned from television. But at the very least, he got to sample the music from everyone's favorite drug scene in Garden State. Again, careful with this at work because the lyrics here have not been censored: the chorus is "In the cut/ in the cut/ rolling doobies up."
In the Cut
After all that, his next single off his freshly minted contract with Atlantic Records is "Black and Yellow," a (hopefully) Pittsburgh Steelers anthem and video that comes rife with Steelers imagery and solid rapping. Young Wiz is all grown up and Wiz Khalifa is here and ready to wreck the Hip-Hop and Top 40 charts for at least the next year or so.
Black and Yellow
[Special thanks to $equel for recommending Kush and OJ.]