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Khalifa was born in Minot, North Dakota to a mother and a father serving in the military. The family moved to Pittsburgh when Khalifa was the age of two. His parents' military service caused the family to move on a regular basis. Over the next decade, Khalifa lived in the U.S., Germany, England, and Japan. Khalifa has been influenced by artists such as Jay-Z, Cam'ron, and the Notorious B.I.G. His stage name is derived from khalifa, an Arabic word meaning "successor", and wisdom, which was shortened to Wiz when Khalifa was 15.

Khalifa released his first mixtape, Prince of the City: Welcome to Pistolvania, in 2005. The mixtape recorded sales in the thousands, leading 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. Khalifa has shared the stage with popular artists like Ghostface Killah, Styles P, Lupe Fiasco, Bone Thugs-n-Harmony, Cham, Little Brother, Clipse, Lil Wayne, Young Jeezy, Lil Scrappy, Mario, T.I., Nas, and Rich Boy. After bringing home “Best Male Artist” and "Lyricist of the Year” at the 1st annual Pittsburgh Hip Hop awards, Khalifa premiered his debut video "Pittsburgh Sound", on various hip-hop fan sites. Khalifa uses, but did not coin, the nickname Pistolvania for Pennsylvania.

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 the 1999 single "Better Off Alone" by the Dutch electronic music group 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".[4] 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. He will release his Warner Bros. debut album, First Flight, in early-2009.