Diddy’s Ups and Downs Over the Years

Sean “Diddy” Combs has faced a lot of ups and downs in his career and personal life.

Diddy began his career in the ‘90s as an intern for Uptown Records after dropping out of Howard University. He worked his way up to become a talent director at the label and went on to help develop artists Jodeci and Mary J. Blige.

After he was fired from the label in 1993, he decided to venture out to create his own label, Bad Boy Records. Under his leadership, he catapulted his own musical career in addition to several other big names, including Faith Evans, Machine Gun Kelly, Notorious B.I.G. and more.

While Diddy proved himself as a successful businessman, he also faced a lot of scandals during his reign, including legal trouble, assault charges, several sexual misconduct allegations and more.

Keep scrolling to see Diddy’s ups and downs over the years:

1991

While working at Uptown Records, Diddy headlined a charity concert with Heavy D at the City College of New York City. The event was oversold and led to a stampede. Nine people were killed. No criminal charges were filed following the incident.

1993

Following his departure from Uptown, Diddy entered a joint venture deal with Arista Records to create Bad Boy Records. His first major client was Notorious B.I.G., whom he brought over from Uptown.

That same year Diddy founded his label, he also welcomed his first child, son Justin, with ex Misa Hylton.

1994

Diddy began dating Kim Porter and adopted her son Quincy from a previous relationship.

1997

Under the stage name Puff Daddy, Diddy dropped his debut single “Can’t Nobody Hold Me Down,” which became his first No 1. song on the Billboard Hot 100. Following the track’s success, he released his debut album, No Way Out. The album included several of Diddy’s most successful songs such as “It’s All About the Benjamins,” “Been Around the World,” “Victory” and “I’ll Be Missing You,” which was a tribute to Notorious B.I.G. who was murdered earlier that year.

1998

Diddy got his first Grammy win when he took home trophies for Best Rap Album and Best Rap Performance by a Duo or Group for “I’ll Be Missing You.”

The same year he also started his Sean Jean clothing line and welcomed son Christian, who goes by the stage name King Combs, with Porter.

1999

The producer was charged with assaulting Interscope Records executive Steve Stoute, who managed Nas. The pair got into a disagreement over Nas’ music video for his song “Hate Me Now,” which Diddy was featured on, and Diddy injured Stoute. Stoute sued Diddy and received a $500,000 out-of-court settlement. Diddy also pled guilty to a charge of harassment and was sentenced to spend one day in an anger management class.

That same year, Diddy also began a brief romance with Jennifer Lopez. While the couple was out at a club in New York City, gunfire broke out after Diddy got into an argument with another patron at the venue. Diddy was charged with four weapons-related charges and with bribing his driver, Wardel Fenderson, to claim ownership of his gun. The case went to trial and Diddy was found not guilty on all charges.

2001

Diddy decided to change his stage name from Puff Daddy to P. Diddy. He also ended Bad Boy’s distribution deal with Arista Records. Diddy was also arrested for driving with a suspended license in Florida. He was released moments later, after he signed a promise to return for a court appearance, per the Associated Press.

2002

Following the success of “I’ll Be Missing You,” Sting sued Diddy for royalties after the rapper used the Police’s “Every Breath You Take” as a sample without permission. Sting won the case and received 100% of the song royalties, with payments reportedly going until 2053.

That same year, Diddy took the reins over the MTV version of Making the Band, which Lou Pearlman originally oversaw for the first season when it aired on ABC. Diddy played a role in helping form Da Band, Danity Kane, Day 26 and Donnie Klang.

2004

Diddy performed at the Super Bowl XXXVIII half-time show.

2005
Four years after his first name change, Diddy announced he was no longer going by P. Diddy and would be known as Diddy from then on.

2006

Porter and Diddy expanded their family with twins D’Lila and Jessie. Five months before Porter gave birth, Diddy fathered daughter Chance with ex Sarah Chapman. He took legal responsibility for his daughter the following year. Porter and Diddy called it quits shortly after that.

2007

Following his breakup from Porter, Diddy began dating Cassie (real name Casandra Ventura), who was signed to his record label.

2015

Diddy was arrested for aggravated assault after an altercation with his son’s football coach at UCLA. The charges were later dropped due to lack of evidence.

2017

Diddy announced that he would now be going by the name Love. Five years later, Diddy clarified that he would still use the stage name Diddy but his legal name was now Sean Love Combs.

2018

Porter died of pneumonia at age 47. Despite being broken up, the pair were on good terms. Diddy delivered an emotional eulogy at her funeral.

“She was my friend first. She was my confidante. She was like my guidance, still is. I was just open,” he said. “We fell in love and honestly, her love was too much for me to handle. It was a lot to handle to take in.”

That same year, Diddy and Cassie called it quits after 11 years of dating.

2022

Diddy welcomed daughter, Love, with Dana Tran, making him a father of seven.

2023

In November 2023, Cassie filed a lawsuit against Diddy accusing her ex of rape, sex trafficking and physical abuse. Diddy denied the allegations.

“Mr. Combs vehemently denies these offensive and outrageous allegations. For the past six months, Mr. Combs has been subjected to Ms. Ventura’s persistent demand of $30 million, under the threat of writing a damaging book about their relationship, which was unequivocally rejected as blatant blackmail,” his lawyer Ben Brafman said in a statement to the New York Times. “Despite withdrawing her initial threat, Ms. Ventura has now resorted to filing a lawsuit riddled with baseless and outrageous lies, aiming to tarnish Mr. Combs’s reputation and seeking a payday.”

Shortly after the filing, the pair reached a settlement.

After Cassie’s lawsuit, more alleged victims came forward with similar allegations. Joi Dickerson-Neal and music producer Rodney “Lil Rod” Jones both accused Diddy of sexual assault. Diddy has vehemently denied the allegations.

“ENOUGH IS ENOUGH,” the rapper told Us Weekly in a statement in December 2023. “For the last couple of weeks, I have sat silently and watched people try to assassinate my character, destroy my reputation and my legacy. Sickening allegations have been made against me by individuals looking for a quick payday.”

Following the allegations, Diddy stepped down as the chairman of his music television network Revolt.

2024

Diddy’s homes in Los Angeles and Miami were raided by the Department of Homeland Security in connection with a federal sex trafficking investigation.

“Earlier today, Homeland Security Investigations (HSI) New York executed law enforcement actions as part of an ongoing investigation, with assistance from HSI Los Angeles, HSI Miami, and our local law enforcement partners,” Homeland Security shared in a statement to Us in March 2024. “We will provide further information as it becomes available.”

During the L.A. raid, his sons, Justin and King, were reportedly detained at the scene, according to TMZ.

Shortly after the raid was carried out, the man accused of being a drug mule for Diddy was arrested on cocaine and marijuana possession charges, per arrest records obtained by Rolling Stone.

In May 2024, CNN released 2016 security footage of Diddy physically assaulting Cassie. After the clip made headlines, Diddy took to social media to apologize.

“It’s difficult to reflect on the darkest times in your life, sometimes you gotta do that,” Diddy said in an Instagram video at the time. “I was f—ked up. I mean, I hit rock bottom but I make no excuses. My behavior on that video is inexcusable. I take full responsibility for my actions in that video. I’m disgusted.”

One week later, Diddy was accused of sexual assault by model Crystal McKinney in a new lawsuit. According to documents obtained by TMZ, the model alleged after meeting in 2003, Diddy drugged her and forced her to perform oral sex on him.