Kelly Osbourne Regrets Quitting Music: ‘Thought About What My Life Would Have Been Like If I Didn’t Stop’

“Will I do anything about that regret? I don't know,” she said on the latest episode of ‘The Osbournes’ podcast

<p>Gilbert Flores/Billboard via Getty</p> Kelly Osbourne in February 2024

Gilbert Flores/Billboard via Getty

Kelly Osbourne in February 2024

Kelly Osbourne is feeling regretful about her music career.

The reality TV star, 39, reflected on her decision to quit music during the July 2 episode of her family’s podcast, The Osbournes, when brother Jack Osbourne, 38, asked if she’s thought about “getting back in the game.”

“I've definitely thought about [getting back into music],” Kelly said. “I've definitely thought about what my life would have been like if I didn't stop. It's definitely a regret. Will I do anything about that regret? I don't know.”

When asked why Kelly decided to leave music behind amid her reality TV fame from MTV’s The Osbournes, her mother, Sharon Osbourne, noted, “She was a rebel,” while her father, Ozzy Osbourne, simply said, “Drugs.”

Related: Kelly Osbourne Shares 'Biggest Regret' from Fashion Police Exit as She Slams Former Co-Host Giuliana Rancic

“I was doing so much TV. I was doing so much touring, and so much publicity, and so many interviews, and I wanted to go out and have fun,” the former Fashion Police host explained of her life at the time. “I didn't want it to be all work and no play, and I didn't know how to even that out and have any balance in my life.”

“And it was bad, but I also covered up a lot of my insecurity,” Kelly added, “and a lot of the naysaying and comparisons and just s--- talking with drugs, so I numbed myself with it. So it kind of went hand in hand with that, with me, and I had to choose myself over all of that.”

<p>Matt Winkelmeyer/Getty</p> Kelly Osbourne at the Grammy Awards on Feb. 4, 2024

Matt Winkelmeyer/Getty

Kelly Osbourne at the Grammy Awards on Feb. 4, 2024

Related: Kelly Osbourne Recalls Executive Saying She Was 'Too Fat for TV' and Could Be Movie Star 'If You Lost Weight'

Kelly first showed signs of a musical future in 2002 with a pop-metal cover of Madonna's 1986 hit "Papa Don't Preach,” per her mother’s suggestion. The “One Word” singer got off to a fiery start with her 2002 rock-driven debut album Shut Up!, but, according to Paper Magazine, she was dropped by her label, Epic Records, two months into touring the LP.

Kelly bounced back in 2005 with the release of her sophomore album, Sleeping in the Nothing, but hasn’t dropped any music since. At the time, she told Paper Magazine she felt forced into a pop-punk box by her former label, which could also be attributed to her musical lineage as the daughter of a rock icon.

"People think I'm a joke and that I'm famous because of who my father is," she said of former Black Sabbath frontman Ozzy. "They wanted that 'F— you, I'm a girl, here's my punk-rock-pop' attitude. They told me what to wear and demanded that I lose weight. And when I didn't want to do it, they said, 'You're 16. You have a record deal. Why are you complaining?' So I didn't say anything."

Kelly hasn’t spoken much about her music career in recent years, although she did share on her family’s podcast that she would consider singing with her father again. She also told her brother, Jack, that watching old basement tapes of her recording music and touring has “definitely made me miss it.”

<p>Jamie McCarthy/Getty </p> Kelly Osbourne in 2020

Jamie McCarthy/Getty

Kelly Osbourne in 2020

Related: Kelly Osbourne Says Her Body Is 'Pickled from All the Drugs and Alcohol'

Following her brief stint in music and four seasons on her family’s reality show in the early 2000s, Kelly fully transitioned to a TV career. She landed gigs as a host and judge on shows like Project Catwalk, Project Runway and Fashion Police. The Life as We Know It actress also competed on ABC's Dancing with the Stars in 2009 and the second season of FOX’s The Masked Singer in 2019.

Along the way, Kelly has admitted to struggling with her sobriety following a history of addiction that dates back to her teen years and the early days of her career. She spoke about those setbacks during a 2021 appearance on Red Table Talk shortly after revealing she relapsed.

Since then, the TV personality has welcomed a son named Sidney, whom she shares with Slipknot DJ Sid Wilson.

Speaking to PEOPLE in 2024 about her motherhood journey, Kelly shared, “It's the best adventure I've ever been on. I can't say enough good things about being a mom. It's just changed everything about my life.”

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