Top 10 Times Celebs Were Ambushed on Talk Shows

In 2004, teenage twin stars Mary-Kate and Ashley Olsen appeared on “The Oprah Winfrey Show” to discuss their booming careers. At the time, there were rumors that Mary-Kate had an eating disorder, but Oprah Winfrey’s couch was probably the last place both sisters expected to be grilled about them. Yet, Winfrey dives right in, urging them to comment on the gossip. Ashley tries to brush it off, but Winfrey prods further, asking the siblings point-blank about their size. It’s an oddly inappropriate line of questioning, especially coming from Winfrey, who has openly discussed her own weight issues. And it’s made even more uncomfortable considering Mary-Kate entered rehab later that year for an eating disorder.

Though they both worked in the same industry, Marc Summers and Burt Reynolds excelled at completely different areas. Summers was a pro at hosting kids’ shows, while Reynolds was the ultimate tough guy on screen. Their paths probably never would’ve crossed had they not both been booked for “The Tonight Show with Jay Leno” on the same night in October 1994. Reynolds was already cranky after Leno joked about his divorce, so when Summers made a similar wisecrack, Reynolds wasn’t having it. What followed was a showdown involving cups of water and a humiliating pie fight. Safe to say, neither of them anticipated ending up in a pastry war when they left their houses that day.

Talking about your sex life can be awkward enough, but imagine doing it on national TV in front of millions. That was the cringe-worthy situation reality TV star Draya Michele found herself in when she appeared on “The Wendy Williams Show” in 2011. Without warning, Williams put Michele in the hot seat, asking her how many basketball players she had been with. Even she realized how bold her question was and tried to justify it by implying that Michele had an active romantic history. From there, the interview spiraled into one wild moment after another, with each of Williams’ statements being more shocking than the last. The discomfort was clearly written on Michele’s face, yet she kept her cool through it all.

WWE bigwig Vince McMahon has dabbled in almost every sport imaginable. But perhaps his most spectacular flop was the short-lived XFL football league, which barely limped through a single season before petering out with little fanfare. This debacle was thrown back in McMahon’s face during a 2001 chat with sportscaster Bob Costas. The interview got off to a tense start, with Costas firing off questions, covering everything from the XFL’s crash landing to the rather unsafe practices at the WWE, and barely giving McMahon a chance to respond. By the end, McMahon was very close to kicking Costas’ butt, which he later admitted he might have done if the host wasn’t physically smaller than him.

By now, it’s no secret that Lindsay Lohan went through a rough patch during the late 2000s and early 2010s. She was still dealing with these issues when she appeared on the “Late Show with David Letterman” in 2013 to promote an upcoming film. But if Lohan was expecting to only talk about the movie, she was definitely in for a surprise as Letterman immediately dived into questions about rehab, which wasn’t on her pre-approved list of topics. While Letterman and his audience seemed to find this amusing, Lohan was visibly uncomfortable and unsuccessfully tried steering the discussion towards the film. At the end of the segment, though, Letterman praised Lohan for enduring his jokes, which made her tear up.

Rosie O’Donnell is no stranger to confrontation. But back in 1999, when she hosted her variety talk show, her image was more warm and fuzzy, which made what happened in this interview quite surprising. The segment, which was meant to promote Tom Selleck’s movie “The Love Letter,” was filmed in the aftermath of the Columbine tragedy. Selleck, a known NRA supporter, found himself in the hot seat as O’Donnell veered off topic to grill him about the organization’s stance on gun control– a topic they had supposedly agreed to avoid. The interview quickly descended into a fiery exchange, with Selleck trying to defend his position and O’Donnell interjecting at every turn. Ultimately, neither party walked away feeling heard or understood.

Celebrities often appear on late-night talk shows to plug their latest projects and Jennifer Aniston was no exception when she graced the “Late Show with David Letterman” in 1998. Aniston was there to promote her film “The Object of My Affection,” but had hardly said a word about it when the interview took a rather disturbing turn. In the middle of their conversation, Letterman suddenly drew closer to the actress and sucked on a strand of her hair. Aniston was laughing throughout the encounter but it was clear that this invasion of her private space made her very uncomfortable. When asked if the experience was traumatizing, Aniston replied with an enthusiastic yes– because honestly, who wouldn’t be?

Talk show hosts love getting the scoop on celebrity news… from the celebrities themselves. Ellen DeGeneres, however, devised a particularly crafty method of doing this when it came to singer Mariah Carey. In 2008, rumors were swirling that Carey was pregnant. Although the buzz was true, Carey wasn’t ready to share the news due to a previous miscarriage. She tried avoiding DeGeneres’ question, but the host then whipped out a bottle of champagne, nudging her to drink and thus confirm the speculation. Carey ended up faking a sip, which was all DeGeneres needed to erupt in cheers. While it might seem like a funny moment, the exchange left Carey feeling uneasy. She sadly suffered another miscarriage shortly after.

Tom Cruise’s 2005 press tour for “War of the Worlds” was nothing short of legendary. Besides his unforgettable couch-jumping on “The Oprah Winfrey Show,” Cruise also had a fiery interview with former “Today” show anchor Matt Lauer. The conversation started off smoothly, focusing on the film and Cruise’s then-girlfriend Katie Holmes. It then took a bizarre turn when Lauer caught Cruise off guard with questions about his criticism of Brooke Shields for using medication to treat postpartum depression. Cruise quickly grew frustrated, passionately defending his stance and lecturing Cruise on the history of psychiatry and the dangers he believed antidepressants posed. This intense face-off between the two unyielding parties remains one of the most contentious interviews in the show’s history.

It was no small task taking Joan Rivers by surprise. The legendary comedian always seemed ready for anything. But when she appeared on “CNN Newsroom” in 2014 to promote her new book “Diary of a Mad Diva,” Rivers probably wasn’t expecting to be quizzed about her style of comedy and choice of attire. Sure enough, those were the questions host Fredricka Whitfield lobbed her way, calling her out for being mean and interrogating why she was wearing fur on her book cover. Rivers was not amused by this line of questioning. She wasted no time in putting Whitfield in her place, then abruptly cut the interview short, proving that “Mad Diva” wasn’t just a title, it was a state of mind.

Which of these interviews shocked you the most? Let us know in the comments below.