Sean ‘Diddy’ Combs launched his career in 1997 with the debut single ‘Can’t Nobody Hold Me Down’ in 1997, achieving incredible success over the years. Despite his accomplishments, he was recently arrested and charged with multiple felonies. Take a look back at photos of the rapper throughout his career.
Not only a respected rapper, Diddy is also an accomplished businessman: he founded the record label Bad Boy Records in 1993, which repped legendary talent like The Notorious B.I.G. and Danity Kane. He has also owned restaurants and designed clothes, just naming a few of his many ventures.
Diddy’s most famous relationships was with the singer Cassie, and actress Kim Porter. Before Kim sadly passed away from pneumonia in 2018, she welcomed three children with Diddy: Christian Combs and twins Jessie and D’Lila. He also adopted Quincy, Kim’s first child. Overall, Diddy has six children, who also include Justin Dior Combs and Chance Combs.
Diddy is one of music’s most famous rappers, and he’s a decent business man to boot. See photos of the star through the years and with his kids.
1 of 23
Diddy’s Twins in St. Barts
Spread Pictures/MEGA
Diddy’s twin daughters D’Lila and Jessie sported bikinis and took selfies while in St. Barts in January 2023. The pair both enjoyed a day on the water.
January 4, 2023, 3:37PM 2 of 23
Diddy and Yung Miami celebrate New Year’s in St. Barts
SplashNews.com
Diddy and his girlfriend Yung Miami celebrate New Year’s Day on his yacht in St. Barts. The couple enjoyed the boat ride with other friends.
January 2, 2023, 2:24PM 3 of 23
Diddy & Christian At The 2022 Billboard Music Awards
Matt Baron/Shutterstock
Sean Combs and Christian Combs buddy up for the 2022 Billboard Music Awards on May 15, 2022. Dad wore his favorite color and Christian was bright in yellow. Christian, 23, is the son of Diddy and Kim.
May 16, 2022, 5:08PM 4 of 23
D’Lila, Chance & Jessie Combs At The 2022 Billboard Music Awards
Image Press Agency/NurPhoto/Shut
D’Lila Combs, Chance Combs and Jessie Combs wow during the 2022 Billboard Music Awards. Chance, 15, is Diddy’s only child with his longtime associate, Sarah Chapman, while twins D’Lila and Jessie, 14, are the youngest of Diddy and Kim’s brood.
May 16, 2022, 5:08PM 5 of 23
Sean ‘Diddy’ Combs Enjoys Yachting
Cobra Team / BACKGRID
Sean Combs aka Diddy soaks up the Italian sunshine before going shirtless on a luxury yacht and showing off his dance moves and kung fu skills in front of Joie Chavis. They looked like they were having a great time.
September 12, 2021, 2:06PM
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Diddy With Joie Chavis
Cobra Team / BACKGRID
Diddy shares a laugh with Joie Chavis on a yacht in Italy. They were dressed in stylish summer outfits. The pair have been linked since 2021.
September 12, 2021, 2:06PM 7 of 23
Diddy With His Daughters In Italy
Cobra Team / BACKGRID
Diddy brought his three daughters Chance, D’Lila, and Jessie on a Gondola ride, while vacationing in Italy in September. The family looked like it was enjoying the end of summer!
September 1, 2021, 12:19PM 8 of 23
Diddy Vacations In Venice With His 3 Daughters
Cobra Team / BACKGRID
Diddy and his three daughters D’Lila, 14, Jessie, 14 and Chance, 15 (twinning in matching leopard dresses) visit Venice, Italy on August 27, 2021. It was ahead of a Dolce & Gabbana event.
August 27, 2021, 10:53PM 9 of 23
Diddy & His Kids At Clive Davis’ 2020 Pre-Grammy Gala
Chelsea Lauren/Shutterstock
Diddy and his children Justin, Chris, Quincy, Jessie, Chance, and D’Lila attend Clive Davis’ 2020 Pre-Grammy Gala at The Beverly Hilton in everly Hills on Jan. 25, 2020. Quincy, 30, is the biological child of Kim and singer Al B. Sure. Diddy adopted Quincy when he was 4.
April 23, 2020, 4:40PM 10 of 23
Diddy Jet Skis With A Mystery Woman & Pals
VEM / MiamiPIXX / BACKGRID
Surprise, surprise! Diddy is seen with a mystery woman as they jet ski at Miami Beach on Jan. 2, 2020. Even more surprisingly, he’s joined by Future, who had just vacationed with Diddy’s rumored ex, Lori Harvey! DJ Khaled and Meek Mill also tag along for the fun outing to kick off the new decade.
January 2, 2020, 8:01PM 11 of 23
Diddy Celebrates Daughter Chance’s Birthday At Disneyland
Marksman/ Snorlax / MEGA
A birthday calls for a family outing to Disneyland! In honor of Chance’s big day, Diddy treats his daughter (along with his other children) to a trip to the theme park in Anaheim, CA in July of 2019. Chance had turned 13 years old.
July 22, 2019, 11:47PM 12 of 23
Sean ‘Diddy’ Combs Presents the Real White Party 2007
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Sean ‘Diddy’ Combs and his sons at Sean ‘Diddy’ Combs Presents The Real White Party in East Hampton New York in 2007. They all matched in white outfits.
March 30, 2020, 2:56PM 13 of 23
Sean ‘Diddy’ Combs At The Premiere Of ‘Spider-Man 3’
Shutterstock
Sean ‘Diddy’ Combs and his kids Justin and Quincy and at the ‘Spider-Man 3’ film premiere at the Tribeca Film Festival in New York in Apr. 2007. The family affair was a night to remember.
March 30, 2020, 2:56PM 14 of 23
Sean ‘Diddy’ Combs At The BET Awards
Shutterstock
Sean ‘Diddy’ Combs poses with sons Quincy and Justin at the BET Awards 2010 at Shrine Auditorium in Los Angeles, CA. They stopped on the red carpet to take a pic.
March 30, 2020, 2:59PM 15 of 23
Sean ‘Diddy’ Combs At The Premiere Of ‘Welcome To My Life’
Shutterstock
Sean ‘Diddy’ Combs and his sons Justin and Christian at the ‘Welcome To My Life’ film premiere in Los Angeles, CA in 2017. The film was a Chris Brown documentary.
March 30, 2020, 2:59PM 16 of 23
Sean ‘Diddy’ Combs & The Kids In 2017
Broadimage/Shutterstock
Sean ‘Diddy’ Combs and his kids Christian, Quincy, Justin, D’Lila, Chance and Jessie at the ‘Can’t Stop, Won’t Stop: A Bad Boy Story’ film premiere in Los Angeles, CA in 2017. They all looked happy to be there supporting him.
March 30, 2020, 3:03PM 17 of 23
Diddy & Cassie At The 2018 Met Gala
Shutterstock
Pictured here at the tail end of their relationship, Diddy and Cassie Ventura match in black and white pantsuits for the 2018 Met Gala in May. The theme was ‘Heavenly Bodies: Fashion and the Catholic Imagination.’
January 2, 2020, 8:26PM 18 of 23
Diddy At A 2003 Marc Jacobs Show
Matt Baron/BEI/Shutterstock
Diddy looks cozy in a fur-lined olive coat at the Marc Jacobs Autumn/Winter 2003 show during New York Fashion Week. He adds an aughts-essential accessory to his outfit: tinted sunglasses.
January 2, 2020, 8:26PM 19 of 23
Diddy At The 2018 Vanity Fair Oscar Party
Matt Baron/Shutterstock
Sean Combs looks handsome in a classic tuxedo at the ‘Vanity Fair’ Oscar party in Los Angeles on March 4, 2018. The bow tie adds a classy touch.
January 2, 2020, 8:26PM 20 of 23
Diddy & Kim Porter At The 2003 CFDA Fashion Awards
Matt Baron/BEI/Shutterstock
Diddy poses with his girlfriend at the time, Kim Porter, at the CFDA Fashion Awards at the New York Public Library on June 2, 2003. The couple dated between 1994 and 2007, and Kim sadly passed away in 2018.
January 2, 2020, 8:26PM 21 of 23
Diddy In ‘Get Him to the Greek’
Snap Stills/Shutterstock
Diddy pays homage to his real-life role as a record executive by playing one in the 2010 comedy, ‘Get Him to the Greek.’ The movie starred Jonah Hill and Russell Brand.
January 2, 2020, 8:26PM 22 of 23
Diddy At Mary J. Blige’s Star Ceremony
Mediapunch/Shutterstock
Diddy celebrates with Mary J. Blige at the legendary singer-songwriter’s star cereomy on the Hollywood Walk of Fame in Los Angeles on Jan. 11, 2018. Diddy worked with Mary while he was a talent director at Uptown Records in the ’90s.
January 2, 2020, 8:26PM 23 of 23
Diddy Celebrated His Birthday And Album Launch
Dave Benett/Getty Images for TAO
Diddy attended his birthday celebration and album launch in November 2023 in London, England, wearing an all-black ensemble topped off with sunglasses.
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