Sean Combs, the hitmaking hip-hop mogul also known as Puff Daddy or Diddy, is facing multiple accusations of sexual assault. In late 2023, he reached a settlement in an explosive lawsuit with Cassandra Ventura, who had alleged that Mr. Combs, 54, raped and physically abused her over about a decade. As part of “an ongoing investigation,” agents from the Department of Homeland Security on March 25 raided homes in the Los Angeles area and Miami connected to Mr. Combs. A key driver of hip-hop’s takeover of mainstream pop, Mr. Combs has had a career in music, fashion and TV for more than 30 years that has been periodically interrupted by run-ins with the law.

1991

An Ambitious Intern’s Rocky Ascent

Mr. Combs, a relatively unknown 22-year-old radio station intern, co-hosted a celebrity basketball game with the rapper Heavy D. A stampede erupted among the jammed crowd inside the oversold City College of New York gymnasium, killing nine people.

A report commissioned by Mayor David N. Dinkins criticized Mr. Combs for allowing inexperienced underlings to plan the event and for tricking ticket buyers about the event’s charitable intentions.

“City College is something I deal with every day of my life,” Mr. Combs said in 1998. “But the things that I deal with can in no way measure up to the pain that the families deal with. I just pray for the families and pray for the children who lost their lives every day.”

A year later, as an intern at Uptown Records, Mr. Combs’s production on the remix of Jodeci’s “Come and Talk to Me” helped the single to sell 3 million copies, announcing him as a rising talent. He went on to help produce remixes for Heavy D, the reggae artist Super Cat, and “Real Love” by the R&B singer Mary J. Blige, which introduced the rapper the Notorious B.I.G.

1994

Starting Bad Boy Records

Mr. Combs’s Bad Boy Records, founded a year earlier after his termination from Uptown, scored its first major success, as the Notorious B.I.G.’s “Ready to Die” album peaked at No. 15 on the Billboard 200. The debut drew critical acclaim for its portrayal of “both the excitement of drug dealing and the stress caused by threats from other dealers, robbers, the police and parents,” as The New York Times wrote at the time, and spawned the hit records “Juicy,” “One More Chance” and “Big Poppa.” To date, the album has been certified six-times platinum.

His work on Blige’s “My Life” album that year garnered his first Grammy nomination (for best R&B album).

1997

Missing the Notorious B.I.G.

Mr. Combs charted some of the most notable accolades of his career before and after the death of B.I.G., born Christopher Wallace, who was killed in a drive-by shooting on March 9, six months after the killing of his rival Tupac Shakur.

Opening the year with the release of “Can’t Nobody Hold Me Down,” Mr. Combs’s first single as the artist Puff Daddy, the song spent six weeks at No. 1 ahead of the anticipated release of a full-length album. Four months after Wallace’s death, “No Way Out,” credited to Puff Daddy & the Family, debuted at No. 1 on the Billboard 200, selling 561,000 copies in its first week and spawning multiple chart-topping singles. The biggest of those, “I’ll Be Missing You,” featured Wallace’s widow, Faith Evans, and the R&B group 112. The requiem, which samples the Police’s “Every Breath You Take,” spent 11 weeks atop Billboard’s Hot 100 chart. The LP earned Combs Grammy wins for best rap album and best rap performance by a duo or group.

That year, four of the 10 songs that reached No. 1 on the Hot 100 belonged to Bad Boy Records.

1999

Arrests for Allegations of Public Violence

After a dispute over the use of footage in a music video, the record producer Steve Stoute claimed Mr. Combs and his bodyguards beat him with a champagne bottle, a telephone, a chair and their fists during an April incident.

Mr. Combs faced up to seven years in prison had he been convicted of felony assault. Instead, Mr. Stoute asked the Manhattan district attorney to drop the charges after Mr. Combs publicly apologized. Mr. Combs had said he was upset that Mr. Stoute, an Interscope Records executive, used footage of him being crucified on a cross in the video for the rapper Nas’s “Hate Me Now.”

“Puff soaked Interscope offices with champagne bottles on Steve/And Steve thought the drama is on me,” Nas wrote in a 2002 song that immortalized the altercation.

That December, an argument broke out at a Manhattan nightclub where Mr. Combs was spending a night out with the actress and singer Jennifer Lopez, his girlfriend at the time.

At least two people were injured by gunfire. The details and timeline of the interaction remained muddled throughout a highly publicized trial. The famed attorney Johnnie L. Cochran Jr. defended Mr. Combs and multiple witnesses testified that the music executive had held a gun. Mr. Combs was charged with gun possession and bribery but found not guilty. His one-time protégé, the rapper Shyne, born Jamal Barrow, received a 10-year prison sentence for assault, gun possession and reckless endangerment.

2002

Making the Band by Making Demands

In 2002, Mr. Combs took over MTV’s “Making the Band,” a reality show aimed at assembling budding rappers and singers into performing groups. The seasons produced the ensemble acts Da Band and Danity Kane, and portrayed Mr. Combs as a demanding boss, who famously made members walk from Manhattan to Brooklyn to secure him cheesecake.

In recent years, multiple band members have spoken out against what they described as mistreatment from Mr. Combs and bad contracts. Da Band’s Freddy P described Mr. Combs as the reason he “hates” life in an Instagram post last year.

That summer, Mr. Combs terminated the label’s joint venture with Arista, leaving the deal with full ownership of Bad Boy Records and its back catalog. Despite the label’s run of R&B hits and attempts to find a rap act of the magnitude of the Notorious B.I.G., Puff Daddy remained its most reliable star.

2003

Back at No. 1

“Shake Ya Tailfeather,” a single from the “Bad Boys II” soundtrack performed by Nelly, Murphy Lee and P. Diddy, as Mr. Combs was then known, hit No. 1 on the Billboard 100 and garnered Mr. Combs’s second Grammy Award for best rap performance by a duo or group (and third overall).

2004-2013

Building an Empire Beyond Music

Mr. Combs expanded his business empire beyond the record industry, earning top men’s wear designer honors from the Council of Fashion Designers of America for his Sean John clothing brand (2004), forging a partnership to release Ciroc vodka (2009) and founding Revolt TV (2013). His portfolio in 2022 is estimated by Forbes to be worth $1 billion.

2015

Another Arrest on Assault Charges

In 2015, Mr. Combs was arrested and charged with assault with a deadly weapon, making terrorist threats and battery after an altercation with a U.C.L.A. football coach. In a news release, the university described the weapon as a kettlebell. Justin Combs, Mr. Combs’s son, began playing football at the university in 2012.

The Los Angeles County district attorney’s office said that prosecutors decided against pursuing felony charges after the incident, according to The Washington Post.

November 2023

An Explosive Lawsuit Interrupts Combs’s Hip-Hop Celebration

Amid the commemorations of the 50th anniversary of hip-hop, Mr. Combs was honored for his pioneering role in the expansion of the genre with a citation as a global icon at the MTV Video Music Awards in September, on the heels of being recognized with a lifetime achievement honor at the BET Awards in 2022.

In November, Mr. Combs’s “