Wiz began his music career as a teenager when Benjy Grinberg, president of Rostrum Records, discovered his talent through a local mixtape in 2004. Impressed by Khalifa’s raw potential, Grinberg signed him to Rostrum and helped guide him through a seven-year artist development journey. In 2005, Wiz released his first mixtape, Prince of the City: Welcome to Pistolvania, followed by his debut studio album, Show and Prove (2006), earning him early recognition as an “Artist to Watch” by Rolling Stone.
His 2007 signing to Warner Bros. Records marked a new phase in his career. He released several mixtapes, including Grow Season and Prince of the City 2, and in 2008, dropped the Eurodance-inspired single “Say Yeah,” his first minor hit, which received substantial urban radio play. However, delays in releasing his official debut album led him to part ways with Warner Bros. in 2009.
Khalifa returned to independence with his second album, Deal or No Deal (2009), and a string of mixtapes that reinforced his growing fan base. By July 2010, he had signed with Atlantic Records and soon released “Black and Yellow,” a Pittsburgh anthem that soared to number one on the Billboard Hot 100 and earned two Grammy nominations. The track cemented his mainstream breakthrough and was the lead single from his major-label debut album, Rolling Papers (2011), which peaked at number two on the Billboard 200.
In 2012, Wiz released O.N.I.F.C., which included hits like “Work Hard, Play Hard” and “Remember You” featuring The Weeknd. His next album, Blacc Hollywood (2014), debuted at number one on the Billboard 200, bolstered by the hit “We Dem Boyz.”
Wiz Khalifa’s biggest commercial success came in 2015 with “See You Again,” featuring Charlie Puth. Created for the Furious 7 soundtrack in tribute to the late actor Paul Walker, the song spent 12 non-consecutive weeks at number one, went 14× platinum, and received three Grammy nominations, becoming one of the most streamed songs of all time.
His sixth studio album, Rolling Papers 2 (2018), matched the success of its predecessor, featuring the sleeper hit “Something New” with Ty Dolla $ign.
Beyond music, Khalifa expanded his brand through acting. He starred in the cult stoner comedy Mac & Devin Go to High School alongside Snoop Dogg and appeared in shows like Dickinson, The Eric Andre Show and voiced characters in American Dad!, Duncanville, and Big City Greens.
In 2008, he founded Taylor Gang Entertainment, a record label and lifestyle brand, signing artists like Juicy J, Ty Dolla $ign, and Berner. Renowned for his marijuana advocacy, he launched the Khalifa Kush cannabis brand in 2016, which expanded to nationwide dispensaries in 2022.
With his smooth flow, dedication to his roots, and entrepreneurial spirit, Wiz Khalifa has become a defining figure of 2010s hip-hop and pop culture. His influence continues to grow as he blends artistry with business, staying true to his laid-back, weed-loving persona while evolving with the times.