The single is a heartfelt song that tells the story of an underground rap artist, his personal problems, and his struggle and desire to achieve success. The rapper composes a song with a doggerel structure and a hook, "Somethin', somethin', somethin' / Stack that Cheese", street slang for making money. Author Charlotte Pence argues that Fiasco achieves simple complexity in the song, rebelling against simplistic lyrics while simultaneously exploiting them.
It was revealed on MTV that the song was partially based on the life and career of Southern rapper Slim Thug and dedicated to Bun B.
The music video, directed by Houston's own Dr. Teeth, was released on March 18, 2008. The video recounts the story of a young up-and-coming rapper and the obstacles he struggles to overcome. The video includes appearances by Slim Thug, Willie D, Nikki Jean, K-Rino, Paul Wall, and Bun B with Lupe Fiasco. In one scene towards the beginning of the video, a clip from the video for "Superstar" (another one of Fiasco's songs) can briefly be seen playing on a television set.