10 Disturbing Diddy Interviews Because of What We Know Now
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VOICE OVER: Emily Brayton
WRITTEN BY: Nick Spake
We should've looked closer at these Diddy interviews. Welcome to MsMojo, and today we're rewinding several interviews that retroactively left us asking, “What did Diddy say?” Our countdown includes "The Wendy Williams Show," "Jimm Kimmel Live!," "Late Night with Conan O'Brien," and more!
10 Disturbing Diddy Interviews Because of What We Know Now
Welcome to MsMojo, and today were rewinding several interviews that retroactively left us asking, What did Diddy say?
Representing
The Wendy Williams Show (2008-22)
After Hot 97 fired Wendy Williams in 1998, she accused Sean P. Diddy Combs of using his money and influence to try to crush [her] in New York. Almost two decades after their beef started, Williams welcomed Diddy onto her talk show, seemingly on good terms. While Diddy presents himself as someone whos matured into a role model, several moments are now traced with irony. Williams inquires about Diddys lifestyle and the people he surrounds himself with, asking if they violate him. She meant financially, but her phrasing proved prognostic. Diddy later discusses setting a positive example for African-American males and his charter school, Capital Prep. Diddys partnership with the school unsurprisingly ended in November 2023 as sexual assault accusations surfaced.
Defending Justin Bieber
Access Hollywood (1996-)
The allegations against Diddy have made people reassess his relationships with several young proteges, including Justin Bieber. Diddys 48 hours with Bieber, in particular, isnt as cool as it seemed in 2009. Although Diddy is in trouble with the law now, the positions were reversed in 2014 when Bieber got arrested for a DUI. Diddy defended Bieber in an Access Hollywood interview. He acknowledged that the pop star had made mistakes, but Diddy vowed to help him stay on the right track. Fast-forward almost a decade, Biebers arrest feels innocent compared to Combs. Bieber wasnt as quick to rush to Diddys defense. A source claims that Bieber doesnt want to focus on Diddys scandal, instead dedicating his time to being a great dad and husband.
Keep J.Los Name Out Your Mouth!
Jimmy Kimmel Live! (2003-)
In late 2023, shortly before Cassie Ventura filed her lawsuit against Diddy, the rapper sat down with Jimmy Kimmel. The host asked about a rumor circulating amid the release of Jada Pinkett Smiths memoir, Worthy. According to somebody claiming to be Diddys former security guard, Will and Jada wanted to have a threesome with Jennifer Lopez. Diddy was dating Lopez at the time, allegedly threatening to beat up Will Smith. Hearing Kimmel relay this tale, Diddy initially responded with a stone-cold stare. He quickly changed his tune, laughing it off and denying such gossip. Whether or not this story is completely fabricated, its far from the most shocking thing Diddy has been accused of. It isnt the most bonkers story involving Will and Jada either.
Hands to Yourself, Diddy
The Keenen Ivory Wayans Show (1997-98)
In the past, if you had P. Diddy and Mike Tyson in the same room, chances are wed be more intimidated by the heavyweight champion. Now, wed be more concerned for Tysons well-being. In 1998, the two appeared on Keenen Ivory Wayans short-lived talk show. If youre curious about the pairing, the boxer wanted to start a music company. While much of the interview feels casual, a blink-and-youll-miss-it dose of awkwardness occurs as Diddys hand gets a little too close to Tyson. Wearing a grin, Tyson removes Diddys hand before scooching away. Perhaps were reading too much into this gesture, but to say that Diddy has been accused of invading personal space would be an understatement. Watching this makes us almost as uncomfortable as Tyson.
73 Questions With Sean Diddy Combs
Vogue
Vogues 73 Questions series allows viewers to connect with celebrities on a more personal level. Admittedly, a lot of these interviews are presented through a rose-tinted lens. Nowhere is that more apparent than in Diddys interview. In 2017, the video presented Diddy in a down-to-earth light. On the heels of his 2024 arrest, though, some of Diddys responses feel like setups for punchlines that late-night hosts would have a field day with. To name a few, Diddy describes himself as eccentric, says that there are no misconceptions about [him], and claims compassion is his best personal trait. Diddy also brings up love several times, even asking the interviewer to refer to him by that name. Oh, and his dream collaboration would be with Michael Jackson.
The Princes & Puffy
The Graham Norton Show (2007-)
Many famous names have quote-unquote partied with Diddy over the years. Not every invitee showed up, however. In 2011, Graham Norton asked about a rumor that Diddy wanted Princes William and Harry to attend one of his parties. Diddy assured Norton that they were no longer on the list. This was seemingly because William was about to marry Catherine Middleton, but Diddys clumsy word choice turned this clip into certified cringe. Diddy claimed that he wanted to party with the princes when they were young bucks growing up. Since the princes had something of a reputation for getting into trouble, Diddy thought theyd want to hang out. Given what allegedly went down at numerous Puffy parties, Diddy mightve felt more at home with Prince Andrew.
Any Interviews with Cassie
Throughout their relationship, Diddy and Cassie Ventura accompanied each other to various red carpet events. Even when flying solo, Diddy and Cassie would often speak adoringly of each other. On the surface, the two looked like the epitome of a glamorous couple. That illusion was shattered when Cassie sued Combs for a cycle of abuse, violence and sex trafficking that allegedly lasted almost a decade. Some of Cassies claims were supported by video evidence. After watching this footage, its impossible to look back on any of their interviews together the same way again. The most disheartening example mayve been at the 2018 Met Gala where Liza Koshy asked Cassie if there was anything shed like to confess. Cassie wouldnt keep quiet much longer.
Chris Brown, Rihanna, & Diddy Too
The Ellen DeGeneres Show (2003-22)
Few couldve predicted that P. Diddy and Ellen DeGeneres would both be problematic figures by 2024. Diddy dropped by DeGeneres show multiple times. Puffy parties were a popular topic. Ellen even invited him to one of her parties. In an especially unsettling interview from 2009, DeGeneres asked Diddy about Rihanna and Chris Brown, the latter of whom had been accused of domestic violence. Diddy reportedly lent Brown his Miami mansion, supposedly attempting to help reconcile his relationship with Rihanna. Diddy didnt deny these claims, saying that he could lend his house to whoever he wanted. While Diddy condemned violence, he argued that stones shouldnt be thrown without all the facts. Unlike Diddy, Brown notably pleaded guilty to his assault charges.
Lock the Doors
Late Night with Conan OBrien (1993-2009)
Between Danny Masterson and P. Diddy, celebs should be careful what they tell Conan OBrien. It may come back to haunt them years later. In Diddys case, Conan spoke with the rapper in 2002. OBrien wanted to learn the key to throwing a Puffy party. Diddy provided a detailed list that included beautiful ladies, beautiful men, booze, water, and locks on the doors. Conan brought the interview to a brief halt, questioning if Diddys parties were safe. Diddy admitted that the locks were a little kinky, although there might be another word for it. Maybe Diddy intended this as a joke, but considering everything thats been reported about his parties as of late, this answer comes off as brutally honest.
Puffys Party Premonition
Entertainment Tonight (1981-)
In 2001, Diddy spoke with Entertainment Tonight about his gun trial, calling it a scary situation. Two years earlier, Diddy gave another interview that foreshadowed his current legal situation. Diddy claimed he couldnt get a permit for his parties, although this wouldnt stop him from throwing them. He suspected that eventually, the authorities would arrest him for trying to have a good time. 25 years after this interview, Diddy was charged with several serious crimes. This includes sex trafficking, which extends to his alleged freak off parties. Combs has pleaded not guilty and time will only tell if the verdict will be in his favor. Given the toll the scandal has already taken on his reputation, though, the party may be over for good.
What do you think is Diddys most notorious interview? Let us know in the comments.
Welcome to MsMojo, and today were rewinding several interviews that retroactively left us asking, What did Diddy say?
Representing
The Wendy Williams Show (2008-22)
After Hot 97 fired Wendy Williams in 1998, she accused Sean P. Diddy Combs of using his money and influence to try to crush [her] in New York. Almost two decades after their beef started, Williams welcomed Diddy onto her talk show, seemingly on good terms. While Diddy presents himself as someone whos matured into a role model, several moments are now traced with irony. Williams inquires about Diddys lifestyle and the people he surrounds himself with, asking if they violate him. She meant financially, but her phrasing proved prognostic. Diddy later discusses setting a positive example for African-American males and his charter school, Capital Prep. Diddys partnership with the school unsurprisingly ended in November 2023 as sexual assault accusations surfaced.
Defending Justin Bieber
Access Hollywood (1996-)
The allegations against Diddy have made people reassess his relationships with several young proteges, including Justin Bieber. Diddys 48 hours with Bieber, in particular, isnt as cool as it seemed in 2009. Although Diddy is in trouble with the law now, the positions were reversed in 2014 when Bieber got arrested for a DUI. Diddy defended Bieber in an Access Hollywood interview. He acknowledged that the pop star had made mistakes, but Diddy vowed to help him stay on the right track. Fast-forward almost a decade, Biebers arrest feels innocent compared to Combs. Bieber wasnt as quick to rush to Diddys defense. A source claims that Bieber doesnt want to focus on Diddys scandal, instead dedicating his time to being a great dad and husband.
Keep J.Los Name Out Your Mouth!
Jimmy Kimmel Live! (2003-)
In late 2023, shortly before Cassie Ventura filed her lawsuit against Diddy, the rapper sat down with Jimmy Kimmel. The host asked about a rumor circulating amid the release of Jada Pinkett Smiths memoir, Worthy. According to somebody claiming to be Diddys former security guard, Will and Jada wanted to have a threesome with Jennifer Lopez. Diddy was dating Lopez at the time, allegedly threatening to beat up Will Smith. Hearing Kimmel relay this tale, Diddy initially responded with a stone-cold stare. He quickly changed his tune, laughing it off and denying such gossip. Whether or not this story is completely fabricated, its far from the most shocking thing Diddy has been accused of. It isnt the most bonkers story involving Will and Jada either.
Hands to Yourself, Diddy
The Keenen Ivory Wayans Show (1997-98)
In the past, if you had P. Diddy and Mike Tyson in the same room, chances are wed be more intimidated by the heavyweight champion. Now, wed be more concerned for Tysons well-being. In 1998, the two appeared on Keenen Ivory Wayans short-lived talk show. If youre curious about the pairing, the boxer wanted to start a music company. While much of the interview feels casual, a blink-and-youll-miss-it dose of awkwardness occurs as Diddys hand gets a little too close to Tyson. Wearing a grin, Tyson removes Diddys hand before scooching away. Perhaps were reading too much into this gesture, but to say that Diddy has been accused of invading personal space would be an understatement. Watching this makes us almost as uncomfortable as Tyson.
73 Questions With Sean Diddy Combs
Vogue
Vogues 73 Questions series allows viewers to connect with celebrities on a more personal level. Admittedly, a lot of these interviews are presented through a rose-tinted lens. Nowhere is that more apparent than in Diddys interview. In 2017, the video presented Diddy in a down-to-earth light. On the heels of his 2024 arrest, though, some of Diddys responses feel like setups for punchlines that late-night hosts would have a field day with. To name a few, Diddy describes himself as eccentric, says that there are no misconceptions about [him], and claims compassion is his best personal trait. Diddy also brings up love several times, even asking the interviewer to refer to him by that name. Oh, and his dream collaboration would be with Michael Jackson.
The Princes & Puffy
The Graham Norton Show (2007-)
Many famous names have quote-unquote partied with Diddy over the years. Not every invitee showed up, however. In 2011, Graham Norton asked about a rumor that Diddy wanted Princes William and Harry to attend one of his parties. Diddy assured Norton that they were no longer on the list. This was seemingly because William was about to marry Catherine Middleton, but Diddys clumsy word choice turned this clip into certified cringe. Diddy claimed that he wanted to party with the princes when they were young bucks growing up. Since the princes had something of a reputation for getting into trouble, Diddy thought theyd want to hang out. Given what allegedly went down at numerous Puffy parties, Diddy mightve felt more at home with Prince Andrew.
Any Interviews with Cassie
Throughout their relationship, Diddy and Cassie Ventura accompanied each other to various red carpet events. Even when flying solo, Diddy and Cassie would often speak adoringly of each other. On the surface, the two looked like the epitome of a glamorous couple. That illusion was shattered when Cassie sued Combs for a cycle of abuse, violence and sex trafficking that allegedly lasted almost a decade. Some of Cassies claims were supported by video evidence. After watching this footage, its impossible to look back on any of their interviews together the same way again. The most disheartening example mayve been at the 2018 Met Gala where Liza Koshy asked Cassie if there was anything shed like to confess. Cassie wouldnt keep quiet much longer.
Chris Brown, Rihanna, & Diddy Too
The Ellen DeGeneres Show (2003-22)
Few couldve predicted that P. Diddy and Ellen DeGeneres would both be problematic figures by 2024. Diddy dropped by DeGeneres show multiple times. Puffy parties were a popular topic. Ellen even invited him to one of her parties. In an especially unsettling interview from 2009, DeGeneres asked Diddy about Rihanna and Chris Brown, the latter of whom had been accused of domestic violence. Diddy reportedly lent Brown his Miami mansion, supposedly attempting to help reconcile his relationship with Rihanna. Diddy didnt deny these claims, saying that he could lend his house to whoever he wanted. While Diddy condemned violence, he argued that stones shouldnt be thrown without all the facts. Unlike Diddy, Brown notably pleaded guilty to his assault charges.
Lock the Doors
Late Night with Conan OBrien (1993-2009)
Between Danny Masterson and P. Diddy, celebs should be careful what they tell Conan OBrien. It may come back to haunt them years later. In Diddys case, Conan spoke with the rapper in 2002. OBrien wanted to learn the key to throwing a Puffy party. Diddy provided a detailed list that included beautiful ladies, beautiful men, booze, water, and locks on the doors. Conan brought the interview to a brief halt, questioning if Diddys parties were safe. Diddy admitted that the locks were a little kinky, although there might be another word for it. Maybe Diddy intended this as a joke, but considering everything thats been reported about his parties as of late, this answer comes off as brutally honest.
Puffys Party Premonition
Entertainment Tonight (1981-)
In 2001, Diddy spoke with Entertainment Tonight about his gun trial, calling it a scary situation. Two years earlier, Diddy gave another interview that foreshadowed his current legal situation. Diddy claimed he couldnt get a permit for his parties, although this wouldnt stop him from throwing them. He suspected that eventually, the authorities would arrest him for trying to have a good time. 25 years after this interview, Diddy was charged with several serious crimes. This includes sex trafficking, which extends to his alleged freak off parties. Combs has pleaded not guilty and time will only tell if the verdict will be in his favor. Given the toll the scandal has already taken on his reputation, though, the party may be over for good.
What do you think is Diddys most notorious interview? Let us know in the comments.
