Nick Cannon reveals the ‘dumbest’ thing he told Oprah and she’s still not over it: "She sees me like..."

Nick Cannon recalls the ‘most awkward moment’ with Oprah Winfrey that he still regrets, admitting things have never been the same
PUBLISHED FEB 28, 2025
Nick Cannon at The GRAMMY Museum; (R) Oprah Winfrey leaves the Empire State Building (Cover Image Source: Getty Images | (L) Photo by Star Max; (R) Photo by James Devaney)
Nick Cannon at The GRAMMY Museum; (R) Oprah Winfrey leaves the Empire State Building (Cover Image Source: Getty Images | (L) Photo by Star Max; (R) Photo by James Devaney)

Meeting someone you admire can be both exciting and nerve-wracking. It’s easy to feel overwhelmed or lost for words. Nick Cannon knows this feeling all too well and regrets what he said when he met Oprah Winfrey. During an interview on 'The Howard Stern Show', Cannon, who hosts 'The Masked Singer', shared an awkward moment from their first real conversation, as per Oprah Daily.



 

"The first time I met Oprah I made the dumbest mistake. Well, it wasn't the first time I met her, because I had seen her in passing and stuff, but at the time, Mariah [Carey] was on the show and we had just gotten married, so this is like my first real face-to-face real conversation with her," Cannon told Stern. "And so we're backstage in Chicago and Mariah just did her thing on the show, and Mariah's like 'Hey Oprah, this is Nick.'" At first, everything was fine. However, Cannon explained that things quickly became uncomfortable.



 

"One of my favorite movies is 'The Color Purple'," Cannon continued. "So this is my opportunity to show Oprah how much I love [The] Color Purple, so the first thing that comes out of my mouth is 'you told Harpo to beat me,'" he said, referring to an emotional and powerful scene from the movie. Unfortunately, Winfrey did not find the comment funny. "She looked at me, and Mariah's like 'I can't believe you just said that s**t.' But I'm thinking everybody's gonna laugh," Cannon said. "Oprah looked at me and we ain't been on the same page since. That was the most awkward moment I've had," CNN reported.



 

Stern asked if Cannon had ever tried to make things right. Cannon admitted they had spoken again but felt Winfrey still held a grudge. "We've seen each other on occasions," Cannon said, "but every time I think she sees me like 'that's that motherf***er.'" During the interview, Cannon also discussed his upcoming plans, including a new project. "I'm going to be a daily talk show host... starting in 2020," Cannon said. "I'm going to have my own show." In other news, Cannon, 44, is a father of 12 children with multiple partners. In November 2024, Bre Tiesi, mother of Cannon's 12th child, Legendary Love, spoke about their unconventional relationship. She clarified that, despite Cannon having other partners, they are together in an open relationship and do not use the term "co-parenting." Tiesi emphasized the absence of jealousy and conflict in their dynamic and spoke about Cannon's active involvement as a father. She also noted her financial independence, stating that she supports herself and their son without relying on Cannon, as reported by People.

Nick Cannon attends the Los Angeles Mission Thanksgiving Dinner at Los Angeles Mission on November 27, 2024 in Los Angeles, California. (Credit Image Source: Getty Images | Photo by Paul Archuleta)
Nick Cannon attends the Los Angeles Mission Thanksgiving Dinner at Los Angeles Mission on November 27, 2024 in Los Angeles, California. (Credit Image Source: Getty Images | Photo by Paul Archuleta)

Just earlier this month, Viacom filed a lawsuit against Cannon, alleging that his new show, 'Bad Vs. Wild,' on the Zeus Network is a replica of his original MTV series, 'Wild 'n Out.' The lawsuit claims that 'Bad Vs. Wild' copies key elements from 'Wild 'n Out' and Cannon's contract with Viacom prohibits such actions. Viacom seeks to halt the production and distribution of 'Bad Vs. Wild' and is pursuing unspecified damages. Currently, neither Cannon nor Zeus Network has publicly responded to the allegations, as per The New York Post.

GET THE BIGGEST ENTERTAINMENT STORIES
STRAIGHT TO YOUR INBOX.

MORE STORIES

Jessica Jones and Matt Murdock were last seen together on the one-season crossover 'Defenders' on Netflix
11 hours ago
The dedication towards the end highlighted how deeply Diego Borella's loss was felt across the production team
12 hours ago
Aileen Wuornos' haunting tale had been previously depicted in the 2003 film 'Monster' starring Charlize Theron
12 hours ago
‘Pluribus’ Season 1 finale ramps up the suspense as Carol faces tough moral choices and Manousos arrives, with fans eagerly awaiting the conclusion
14 hours ago
Fans were soon disappointed when they tuned in on December 18 for a new 'Matlock' Season 2 episode but found none.
15 hours ago
Created by Darren Star, Season 5 shifts its focus to Emily’s romance with Marcello, leaving fans questioning Gabriel's place in her story
16 hours ago
The new 'Pluribus' fan theory stems from a scene in which Carol is seen driving around town in a police car
17 hours ago
Carol continued to research the Hive Mind in the latest episode of 'Pluribus', uncovering deeper insights about the Joining
19 hours ago
The singer released the first two episodes of new docuseries about the Eras Tour last week
1 day ago
The show tracing the sleuth's early years releases March 4, 2026 with all episodes dropping together
1 day ago