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Combs' debut album, No Way Out (1997), has been certified seven times platinum. The album was followed by Forever (1999), The Saga Continues... (2001), and Press Play (2006), all of which were commercially successful. In 2009, Combs created and produced the musical group Diddy – Dirty Money; they released their successful debut album Last Train to Paris in 2010.

Combs has won three Grammy Awards and two MTV Video Music Awards and is the producer of MTV's Making the Band. In 2022, Forbes estimated his net worth at US$1 billion. In 1998, he launched his own clothing line Sean John. He was nominated for the Council of Fashion Designers of America (CFDA) Award for Menswear Designer of the Year in 2000 and won in 2004.

In late 2023, Combs settled a high-profile sexual assault and abuse lawsuit filed by his former partner Cassie Ventura. Numerous lawsuits regarding sexual misconduct were filed in the following months, with several claimants alleging sexual assault and abuse by Combs between 1991 and 2009. A year later, several of Combs's properties were raided by the Department of Homeland Security, and that September he was charged with federal sex trafficking, transportation to engage in prostitution, and racketeering. In May 2025, Combs was criminally tried for sex trafficking, racketeering and transportation to engage in prostitution. He was found not guilty in all but two transportation charges, for which he was sentenced to 4 years and 2 months in prison and a $500,000 fine.