Jay-Z might have 99 problems, but a career isn’t one. Born Sean Carter in the New York City borough of Brooklyn, the undisputed king of rap showed his entrepreneurial ambition early on when his debut album Reasonable Doubt was released in 1996 on his own, newly-formed label Roc-a-Fella Records. The record generated four charting singles and rose to as high as number 23 on Billboard’s album chart. The album’s popularity was helped by Jay’s collaborations with hip-hop heavyweights such as DJ Premier, Notorious B.I.G. and Mary J. Blige, as well as samples from artists like Nas.

Jay-Z’s follow-up album, In My Lifetime Vol. 1, reached number three on the Billboard chart and sold a lot better than Reasonable Doubt as the bulk of the tracks seemed to distance Jay from the more hardcore style of gangster rap that was prominently featured on his debut effort. His next album, 1998’s Vol. 2: Hard Knock Life, was a major breakthrough, spawning hits like “Can I Get A…”, “Cash, Money, Hoes and “Hard Knock Life” where he famously sampled the song of the same title from the musical Annie. The record won a Grammy for Best Rap Album.

Jay established himself as a rap powerhouse when the success of Vol. 2 was followed by the similarly heralded Vol. 3: Life and Times of S. Carter, which reached the top of the Billboard charts and produced mega-hit “Big Pimpin.’” After an album featuring an array of appearances by acts from his Roc-a-Fella stable of artists, Jay-Z released The Blueprint in 2001. The Blueprint solidified Jay’s position atop the rap throne when “Izzo (H.O.V.A.)” was arguably the year’s biggest song.

After a few collaborative efforts and hit singles, Jay-Z announced to the world that he would be retiring after the release of his 2003 effort The Black Album. The record climbed to number one and turned out a few hits, as per usual at this juncture for the superstar. He capped off what looked to be the end of his rapping career with a farewell tour and prepared for retired life.

Apparently, retired life meant a busier one for Jay-Z. He accepted an offer to assume the position of president of Def Jam Records shortly after retiring. Since then, Jay has discovered and jumpstarted the careers of a number of new, talented artists and eventually came out of retirement in 2006 when he released Kingdom Come. His subsequent album, 2007’s American Gangster, was inspired by the major motion picture of the same name.

Jay-Z is one of the most successful rappers in the history of the genre and has seated himself among such greats as 2-pac and Biggie. He’s one of the most recognizable musicians in the world and has his hand in many different media ventures. He’s also part-owner of the New Jersey Nets, a professional basketball franchise, and has developed friendships with star athletes like LeBron James. It’s obvious that there’s no stopping this hustler turned businessman.