In 1993, after being fired from Uptown, Combs established Bad Boy Entertainment as a joint venture with Arista Records, taking The Notorious B.I.G., from Uptown, as well as Faith Evans. Starting with Craig Mack's hit single, followed by B.I.G.'s Ready to Die. Diddy signed, Carl Thomas, 112, and Total. Mase and the Lox joined Bad Boy just as a the rivalry with the West Coast's Death Row Records was beginning, while Diddy produced several songs for TLC's CrazySexyCool, which finished the decade as number 25 on Billboard's list of top pop albums of the decade.
In 1997, under the name Puff Daddy, Combs recorded his debut single, "Can't Nobody Hold Me Down", which spent 28 weeks on the Billboard Hot 100 chart, peaking at number one. His debut album, No Way Out, underwent several changes after B.I.G. was killed, the album reached number one on the Billboard 200 in its first week of release, selling 561,000 copies, and producing five singles: "I'll Be Missing You", a tribute to The Notorious B.I.G., which became the first rap song to debut at number one on the Billboard Hot 100 and remained at the top of the chart for eleven consecutive weeks. "Can't Nobody Hold Me Down", "It's All About the Benjamins", "Been Around the World", and "Victory", followed. The album earned five nominations at the Grammy's in 1998, winning the Grammy Award for Best Rap Album. The album was certified septuple platinum with sales of over 7 million.
Forever, Combs's second album, reached number two on the Billboard 200 and number one on the Top R&B/Hip-Hop Albums chart. Combs changed his stage name from "Puff Daddy" to "P. Diddy" in 2001, and he appeared as a drug dealer in the film Made and starred with Halle Berry and Billy Bob Thornton in Monster's Ball. Combs ended Bad Boy Entertainment's joint venture with Arista Records, gaining full control of Bad Boy, its catalogue, and its roster of artists.
The Saga Continues..., was the last studio album released by the joint venture. The album reached number 2 on the Billboard 200 and the Top R&B/Hip-Hop Albums charts, and was certified Platinum, as the only studio album under the P. Diddy name.
Combs released Press Play, in 2006, debuting at number one on the Billboard 200 with sales of over 173,009. "Come to Me" and "Last Night" both reached the top ten of the Billboard Hot 100. Press Play was certified Gold, as Diddy teamed up with 50 Cent and Jay-Z for the "Forbes I Get Money Billion Dollar Remix".
Last Train to Paris was released by Combs's group Dirty Money in 2010. The four singles "Angels", "Hello Good Morning", "Loving You No More", and "Coming Home", experienced success on the Billboard Hot 100. "Coming Home" was the most successful of the songs, peaking at number twelve on the U.S. Hot 100.
Producer, Label Owner, Artist, Actor, and Business Mogul, whatever label or name you want to give him Diddy has and always will translate to success.