Wendy Williams and Sean “Diddy” Combs haven’t been on the best terms over the years.
The drama between the pair began in the ‘90s when Williams spoke out against Diddy on her radio show Hot 97 on multiple occasions. In 1998, Williams was fired from the radio show and has maintained a “belief” that Diddy played a role in it.
Despite parting ways with the radio station, Williams found success with her talk show, The Wendy Williams Show, which premiered in 2008. During her daytime TV reign, she covered a wide array of Diddy news including his various legal dramas.
After years of ups and downs, Diddy and Williams seemingly buried the hatchet when he appeared on her show in 2017. (The show’s finale episode aired in 2022.)
“I know I piss off a lot of people, including you, but this is a full circle moment,” Williams said after Diddy gave her props for being one of the first female hip-hop journalists. “Everybody get into adult conversation.”
Keep scrolling to see what Williams has said about Diddy over the years:
Getting Jumped
Before getting fired from Hot 97, Williams claimed in 2005 during her radio show, The Wendy Williams Experience, that she was almost jumped by the girl group Total, who was signed to Diddy’s record label Bad Boy Records. Williams recalled the alleged moment and hinted that Diddy was involved during a 2019 episode of her talk show.
“Once upon a time, there was a music mogul who sent his all-girl group to beat my ass in front of the radio station. Fact!” she claimed. “I finished my shift, round up my headphones, put my bag [on] my arm and I see everybody lined up at the window looking down on the sidewalk.”
Williams explained that she was dating ex-husband Kevin Hunter at the time and they had encountered the musical act.
“I find this girl group, jump out of a gypsy cab, to come after me,” she alleged. “To beat my ass! For what? You know what I said was true. You all were broke and you were living in the projects, and that was that.”
Her Firing
During a 2013 interview with Vlad TV, Williams tiptoed around her firing from Hot 97 and how it revolved around her speculation about hip-hop musician’s sexuality.
“There was a radio personality once upon a time and her name was Wendy Williams and she was practically burned at the stake for talking about such and now it’s all come full circle,” she teased. “There were many situations back in the day in my career and it’s all coming full circle.”
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His Name Changes
Williams, who always refers to the rapper as Puffy, poked fun at him constantly changing his name throughout his career.
“I don’t like when people change their names in the middle of our relationship,” she quipped in a 2015 episode of The Wendy Williams show. “Like don’t tell [to] me call you Diddy, I know you as Puffy, that’s it.”
Her Book Revelations
In her 2004 book, The Wendy Williams Experience, she wrote that she had “a certain level of contempt for Puff” because he “single-handedly tried to ruin” her career.
“The hell he put me through,” she penned. “I will never forget. But I don’t hate him.”
Alluding to Controlling Tendencies
After Diddy and Cassie (real name Cassandra Ventura) briefly broke up in 2015, Williams speculated that there was a balance of power issue between the record producer and singer.
“My thing about when you date a mogul, it’s really difficult to avoid them because if you use your head you never know when they’ll pop up on the scene,” she said on The Wendy Williams Show. “He can hire a plane right now … land on the roof of the hotel she’s staying, pay people off at the front desk, ‘Give me a key and let me up in her room.’ I’m already paranoid as a person.”
Calling Out His Playboy Nature
Williams quipped that she didn’t think Diddy would want to settle down when he reached the age range of “68 to 78” due to his party boy lifestyle.
“He’ll pick [a woman] and settle down but right now I don’t think he will,” Williams claimed on a 2015 episode of her series. “I think he’s leading this playboy lifestyle where he’s got these women in his life … where he’s got them hypnotized.”
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On His Guest Appearance
Three years after his interview with Williams, the talk show host opened up about the rivals’ full circle moment.
“He showed up, he smelled great, his stomach was flat. Heather, he was handsome and he ain’t going nowhere. Can’t be stopped now,” she said during a 2019 interview on the Sway’s Universe radio show. “Bad Boy for life.”
Weighing in on Cassie and Diddy’s Split
When Diddy and Cassie called it quits for good in 2018, Williams was initially rooting for the pair to get back together since Diddy publicly declared his love for Cassie on Williams’ talk show. However, after seeing Diddy attempt to win Cassie back on social media, Williams labeled his behavior as manipulation.
“I suggest don’t use social media though to reach out. I think this was a grand overture from Puffy. I don’t believe he really wants her back,” she said at the time. “I believe he probably treated her, at some point, like a possession. If you really cared then you’d reach out privately not publicly.”
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On Diddy’s Arrest and Investigation
Less than a month after Diddy was arrested in New York and indicted on charges of racketeering and sex trafficking, Williams decided to speak out about the ongoing legal case.
“What is really weird is that I have been told by so many people, ‘Wendy, you called it,’” she told the Daily Mail in October 2024. “Including some people from my family who have said the same. You know how I feel about that? It is about time. To see this video on TV of [Cassie] getting pummeled … it was just horrific. But now you have to think, how many more times? How many people? How many more women? It’s just so horrible.”
The rapper has refuted all of the allegations against him and pleaded not guilty.
