A clip where Sharon Osbourne jokes to Kelly she would like to be Sean Combs’ mother-in-law went viral earlier this year after the rapper was found guilty of transportation for prostitution

HOLLYWOOD, CA - AUGUST 22: Jack Osbourne and Kelly Osbourne arrive at the screening of "God Bless Ozzy Osbourne" to benefit the Musicares Map Fund held at ArcLight Cinerama Dome on August 22, 2011 in Hollywood, California. (Photo by Jeff Kravitz/FilmMagic)
Jack and Kelly Osbourne

Jack Osbourne claims his sister Kelly Osbourne “ended up winning” following an encounter with music executive Sean “Diddy” Combs. Earlier this year resurfaced clips showed Sharon Osbourne encouraging Kelly to pursue a romantic relationship with the now-disgraced hip-hop mogul.

During The Osbournes episode, Sharon declared: “Wouldn’t it be cool if Kelly went out with Puff Daddy? And I was Puff Daddy’s mother-in-law? Puff Mummy. I think they would be so cute together.”

Subsequently in the show when Kelly arrived home from the event, she displayed the timepiece Combs had gifted her. Kelly informed Sharon: “Mum, he’s so manicured, he’s such a gentleman, he’s so well put together.”

Sharon Osbourne, Jack Osbourne, Ozzy Osbourne and Kelly Osbourne
(Image: Getty Images)

While the praise continued, Sharon interjected with her own observation, declaring: “I bet he’s got a nice old willy and all! I bet it’s smooth. I bet it’s oiled. I bet it’s just perfect.”

Kelly then shrieks and responds: “Stop, it’s making me sick.”

Last year Sharon said she “never knew” about Combs’ crimes. She claimed he was “always very pleasant” and “beautifully respectful”.

During an episode of the Inside of You podcast with Michael Rosenbaum, her son Jack, 39, recounted an incident involving his sister Kelly and Combs. He shared: “Kelly got invited to a Diddy party when she was like 18 and like, he ran into Kelly, and some weird thing happened where his bouncer knocked her over and he invited her to one of his parties.”

Kelly Osbourne with Sean Combs
Kelly Osbourne with Sean Combs(Image: Dimitrios Kambouris/WireImage)

Jack says there was speculation about what happened when the two met. He added: “I think she ended up winning that, he gave her some diamonds and brought her to a party and she went, ‘Later’.”

Since their reality TV days on The Osbournes, Jack has made appearances on numerous television shows including Jack Osbourne: Adrenaline Junkie, the X Factor, and Dawson’s Creek. He’s also been involved in several paranormal-themed TV shows.

Currently, Jack is featured on ITV One’s Cooking with the Stars, airing at 6.55pm. This week’s finale will see him competing against EastEnders legend Natalie Cassidy and interior design guru Kelly Hoppen.

Speaking about his participation in the show, Jack explained: “I have a complicated household when it comes to eating. I have four daughters and their ages are 13, nearly 10, seven and nearly three.