Bob Marley

Khalifa released his first mixtape, Prince of the City: Welcome to Pistolvania, in 2005. The mixtape led to his first full length album entitled Show and Prove in 2006. Khalifa was declared an "artist to watch" that year in Rolling Stone magazine.[9][10]

In 2007, Khalifa signed to Warner Bros. Records and released two mixtapes through Rostrum Records: Grow Season, hosted by DJ Green Lantern and released on July 4, 2007, and Prince of the City 2, released on November 20, 2007. His debut Warner Bros. single "Say Yeah" reached number 25 on the Billboard Rhythmic Top 40 music chart and number 20 on Billboard's Hot Rap Tracks. The song samples "Better Off Alone" by Alice Deejay. Khalifa's vocals from "Say Yeah" appear near the end of Pittsburgh mash up producer Girl Talk's 2008 album, Feed the Animals, over music from Underworld's "Born Slippy", Usher's "Love in This Club", and the Cure's "In Between Days".[11] Khalifa appeared with The Game, David Banner and Play-n-Skillz at U92's Summer Jam at the USANA Amphitheatre in West Valley City, Utah on August 2, 2008.[12] Khalifa released the mixtapes Star Power in September 2008, and Flight School in April 2009 on Rostrum Records.

Khalifa parted ways with Warner Bros. Records in July 2009 after numerous delays in releasing his planned debut album for the label, First Flight. Khalifa stated to the Pittsburgh Post-Gazette that, "I learned a lot during my time there and matured as an artist during the process. I'm happy to be moving on with all of my material and having the chance to be in control of my next moves".[13] Khalifa appeared with Girl Talk, Modey Lemon, Donora, Grand Buffet, and Don Caballero at the Amphitheatre at Station Square in Pittsburgh on July 31, 2009, where he announced that his relationship with Warner Bros. was over