In April 1999 Combs was charged with assault as a result of an incident with Steve Stoute of Interscope Records.Stoute was the manager for Nas, with whom Combs had filmed a video earlier that year for the song "Hate Me Now".He was born in Harlem and was raised in Mount Vernon, New York.

On February 26, 2014, Combs premiered "Big Homie", featuring Rick Ross and French Montana, as the first single from his mixtape MMM (Money Making Mitch), which was originally scheduled to be released that year.

In July 2015, Bad Boy Entertainment artist Gizzle told the press that she is collaborating with Combs on what she describes as his last album, titled No Way Out 2, a sequel to his 1997 debut.

Four other singles; "Can't Nobody Hold Me Down", "It's All About the Benjamins", "Been Around the World", and "Victory", were also released.

Combs collaborated with Jimmy Page on the song "Come with Me" for the 1998 film Godzilla.

The event was oversold, and a stampede occurred in which nine people died. In 1997, under the name Puff Daddy, Combs recorded his first commercial vocal work as a rapper.

Mase and the Lox joined Bad Boy just as a widely publicized rivalry with the West Coast's Death Row Records was beginning. His debut single, "Can't Nobody Hold Me Down", spent 28 weeks on the Billboard Hot 100 chart, peaking at number one. Several of the label's artists made guest appearances on the album.

After a police investigation, Combs and fellow rapper Shyne were arrested for weapons violations and other charges. Lawyers for both sides, having agreed to keep the settlement terms secret, said that the matter was "resolved to the satisfaction of all parties".

The Saga Continues..., released on July 10 in North America, was the last studio album released by the joint venture.

His debut album No Way Out (1997) has been certified seven times platinum and was followed by successful albums such as Forever (1999), The Saga Continues... In 2009, Combs formed the musical group Diddy – Dirty Money and released the critically well-reviewed and commercially successful album Last Train to Paris (2010).