Khalifa’s parents served in the military, which led to a transient upbringing. Following their divorce when he was three years old, Khalifa spent much of his childhood in various countries, including Germany, Japan, and the United Kingdom. He eventually settled in Pittsburgh, Pennsylvania, where he attended Taylor Allderdice High School.

Early Career and Breakthrough

In the early stages of his career, Khalifa performed locally, mainly for enjoyment and modest income. His talent caught the attention of Benjy Grinberg, president of Rostrum Records, who signed him in 2004. This partnership led to the release of his debut mixtape, Prince of the City: Welcome to Pistolvania, in 2005.

In 2006, Khalifa released his debut studio album Show and Prove, which helped him gain critical recognition. Rolling Stone named him an "Artist to Watch," boosting his profile further. In 2007, he released two mixtapes under Warner Bros. Records. That same year, his single "Say Yeah" became his first track to chart on the Billboard Hot 100, reaching No. 20 on the Hot Rap Tracks chart.

Commercial Success and Mainstream Reception

In 2009, Khalifa parted ways with Warner Bros. due to delays in releasing his music. He returned to Rostrum Records and dropped the track "Teach U to Fly." The turning point in his career came with the release of the 2010 mixtape Kush and Orange Juice. Distributed for free, its quality and viral appeal—particularly on Twitter and Google—solidified his status as a major artist in the rap scene.

The single "Black and Yellow," released later in 2010, became a cultural phenomenon. Serving as a hometown anthem for Pittsburgh, the track reached No. 1 on the Billboard Hot 100, marking his breakthrough into mainstream success.