The Most Uncomfortable Oprah Interviews Ever

Oprah Winfrey is without a doubt one of television's most prolific and lauded interviewers. According to her own O magazine, she interviewed around 28,000 guests during her tenure as host of The Oprah Winfrey Show, which debuted in 1986, and concluded its 25th season in 2011. According to CNN, Oprah has won 16 Daytime Emmy Awards to date and has continued interviewing people for various programs on her OWN TV network and in the pages of her magazine.

Given these impressive stats and the many years she's been chatting with people both on air and in print, it's not surprising that a few of her interviews stand out for the level of discomfort they induce in the viewer. We've rounded up the Oprah convos that brought on the awkward factor in a major way. Read on to experience the uncomfortable interview moments that even the "Queen of All Media" couldn't conquer.

During a 2003 appearance on The Oprah Winfrey Show, songstress Barbra Streisand made a bold sartorial move that didn't go unnoticed by Oprah. Streisand not only wore a white turtleneck, but brought along her white, tiny, fluffy dog named "Sammie." After a musical performance, Streisand introduces Sammie, and then Oprah bluntly calls Streisand out on matching her turtleneck and her dog to her microphone, which was also mysteriously white. Just before commercial break, Oprah addresses the camera and Streisand, saying, "I want to just say this ... I own this studio, I've been here I don't know how many years. I've never seen a white mic."

Streisand, who is sitting in a Bond villain-esque pose holding "Sammie," promptly corrects Oprah: "It's actually off-white, to match my off-white sweater." The songstress continues, "I like simplicity, and monochromatic frames." 

"So you had the mic sprayed?" Winfrey presses. 

"That's right," Streisand curtly replies. Cut to commercial.

Comedian Kathy Griffin described the awkward interaction between the two women in her 2009 book, Official Book Club Selection, writing that the two women "appeared to go at it like they were in a Mexican c**kfight ... And it had been eating at Oprah for weeks."

Musician Mackenzie Phillips dropped a bombshell during a 2009 appearance on The Oprah Winfrey Show to publicize her memoir, High on Arrival. Along with candidly talking to Oprah about her struggles with drug addiction and her troubled childhood, Phillips read a passage from the book in which she describes having had a ten-year long incestuous relationship with her father, John Phillips, who was the leader of the '60s band The Mamas & The Papas.  

You can hear a pin drop when Oprah asks Phillips to read the passage. "Wow," Phillips responds, nervously. "This wasn't exactly how I envisioned this going down, but that's all right..." (It doesn't feel all right.) "Get to it," Oprah snaps.

Phillips' revelation spawned conflict within her own family, and in 2016, she returned for a segment on OWN's Where Are They Now. In that interview, Phillips discusses the terrifying experience on Oprah's talk show. "I felt, here I was with this huge piece of information that maybe wasn't even fit for public consumption ... In retrospect there was some due diligence I missed doing, like preparing myself for losing my family." 

In one of the most bizarre displays of new relationship excitement ever caught on camera, movie star Tom Cruise made viewers feel, in the modest words of VH1 News, "weirded out" during a May 2005 interview on The Oprah Winfrey Show.

Cruise was supposedly there to promote War of the Worlds, but the conversation quickly turns to his blossoming romantic relationship with Dawson's Creek star Katie Holmes. Unable to control himself, a triumphant Cruise jumps up and down on Winfrey's couch, pumping his fists in the air. An incredulous Oprah can only say, "He's gone. He's gone. The boy is gone." Though the audience cheers, viewers at home and journalists alike were left seriously confused by Cruise's bizarre behavior.

In August 2018, The Ringer described how Cruise's appearance on Oprah prompted a cascade of internet memes and media commentary, "most of it overwhelmingly negative." According to the site, "Instead of making people think he was a romantic, Cruise just made people think he was weird."

Footprints on studio couches aside, Holmes and Cruise divorced in 2012. 

When Oprah Winfrey selects a book for Oprah's Book Club, it's all but guaranteed to hit bestseller lists nationwide. In 2006, she conferred Book Club status on author James Frey's harrowing memoir A Million Little Pieces, in which Frey narrates his descent into and struggles recovering from alcoholism. Just three months later, however, The Smoking Gun unearthed evidence that Frey had fabricated aspects of his story, which led to one of the most uncomfortable interviews in Oprah history.

Oprah invited Frey to her show to explain himself. The ensuing conversation makes for seriously nerve-racking watching as an obviously PO'd Oprah takes aim at the author with precision through her line of questioning. "I feel that you conned us all. Do you?" Oprah asks. She later says, "I think you presented a false person." (You can read the full transcript here.) TIME called the interview "the most spectacular media-élite street brawl." 

And yet, in 2011, Oprah (who reportedly apologized to Frey in 2009 for her treatment of him during that 2006 interview) invited the author back to her show to make amends, telling him that despite the falsities contained in the book — which will reportedly be adapted for a movie starring Billy Bob Thornton — it has helped other people dealing with addiction. 

During Oprah's January 2013 interview with disgraced cyclist Lance Armstrong, she confronts him with incredibly direct questions about his use of performance enhancing drugs. One of the most cringe-inducing moments occurs when Armstrong attempts to make a joke about Betsy Andreu, the wife of his former cycling teammate, Frankie Andreu. 

Betsy had publicly criticized Armstrong for lying about his drug use, and so Oprah asks Armstrong about things he'd reportedly said about Betsy. Armstrong recalls a conversation with Betsy like this: "I said 'listen, I called you crazy. I called you a b**ch. I called you all these things, but I never called you fat.'" Gawker aptly describes what happens next: As Armstrong waits for a laugh from Oprah at what he seems to consider an amusing anecdote, "the camera cuts to a brilliant shot of Oprah blinking at him, her eyelids heavy under the weight of gravitas."

According to The New Yorker, perhaps the most discomfiting aspect of Armstrong's interview with Oprah was that, despite admitting to using illegal substances, he still seemed to show little remorse for hurting others. 

Oprah Winfrey made a gaffe similar to something an embarrassing untie might pull during her 2010 sit down with NFL quarterback Drew Brees. After excitedly exclaiming, "Wow, wow, wow, wow, wooooo!" she attempts to wipe what she perceives to be a smudge of lipstick off his cheek, saying, "Who just kissed you?" Brees politely holds his hand up and laughs it off.

In 2012, Brees told CNN that he'd been made fun of as a child because of his birthmark, but he decided to forgo surgery and keep his unique feature. In his book Coming Back Stronger (via ABC News), he writes, "Instead of seeing it as a bad thing, I chose to see it as something that made me unique and special. It set me apart from everyone else. ... Now it's just a part of who I am. I wouldn't consider cutting off my arm. Neither would I cut off my birthmark."

In this case, an overeager fan named Christina from Ontario was the root of everyone's discomfort — Oprah Winfrey included — during a 2008 interview with actor Brad Pitt. Joined by his Curious Case of Benjamin Button co-star Cate Blanchett, Pitt fielded questions from fans via Skype. When it's her turn, Christina gets straight to the point, congratulating a stone-faced Pitt on "finding love with Angelina ... you fit together seamlessly," and asking the actor about the meaning behind his tattoos.

Pitt demurs and simply says, "If you have a partner, it's great fun, it's a great thing to go do together. It becomes personal and special in its own right. I'd rather just leave it at that." Christina, however, clearly doesn't want to leave it at that, asking, "Even the iceman?" 

"What are you talking about?" Winfrey says, so Christina proceeds to describe several of Pitt's tattoos in detail as a visibly uncomfortable Pitt shifts in his seat. "How do you know this?" Winfrey presses. 

"I've been a fan for about 17 years," Christina says, telling Pitt, "I know you've got [a tattoo] on your tummy, don't make me go there!" Mercifully, the exchange ends shortly thereafter. 

Luckily, footage exists of Oprah Winfrey's excruciatingly uncomfortable Feb. 1, 1988 interview with Hollywood legend Elizabeth Taylor. A subdued Taylor is markedly withholding throughout the conversation. According to Oprah.com, the talk show queen says that interview is "still painful to watch ... For many reasons — including my bad hair." 

Prior to the interview, Taylor had requested that there be no questions about her relationships, which Oprah did not abide. Per The New Yorker, the actress responds to one of Oprah's probing inquires with, "None of your business" and a "hyacinth death stare." 

According to Oprah.com, "Liz's responses were so terse that Oprah couldn't help but tease, "You're so revealing — you just tell everything! I declare, you've got to stop talking so much, Ms. Taylor!" 

Despite this memorably awkward exchange, Taylor continued to appear on the show over the years.

You know that feeling when you're out with a couple and they start to fight, and everyone just sits there in silence, waiting and praying that it'll all be over soon? That was kind of the vibe during author Terry McMillan's 2005 appearance on The Oprah Winfrey Show. According to People, the author of Waiting to Exhale and How Stella Got Her Groove Back sat down with her ex-husband, Jonathan Plummer. The pair divorced after Plummer came out as gay.

The ex-couple argued for much of the incredibly tense interview, with McMillan telling Oprah that she was shocked to learn her husband had been leading a double life. When asked if the pair could be friends, Plummer replies, "We're taking our time," while an exasperated McMillan insists, "No, we're not!" adding, "We're not going to be kicking it."

A friend naming their child after you is one thing, while a rando naming their dog after you is quite another. Such was the awkward situation that Oprah Winfrey sat down to remedy with rapper 50 Cent for Oprah's Next Chapter in 2012.

According to a 2006 interview with the Associated Press, 50 Cent had beef with the talk show host, claiming she wouldn't have rappers on her talk show because she "caters to older white women" and complaining that during a 2005 appearance on her show to promote his work in the movie Crash, "she gave me a hard time as a rapper, when I came on there as an actor." But, 50 Cent noted, "I'm actually better off having friction with her."

Cut to six years later, and 50 Cent's comments were looming large during his interview with Oprah. The pair slowly but surely unpacks the rumored feud, and in a moment that saw 50 Cent sweating in the hot seat, Oprah confronts him about naming his dog after her, saying, "That was not a compliment." 

50 Cent responds, "At the time, I was just looking at the situation and I saw I was developing negative feelings for someone who doesn't even know me, and I gave it to the dog, cause I was excited about the dog at the time."

Everything was apparently squared away by the end, when Oprah asks, "Now do you have greater affection for me?" 

"Absolutely," 50 Cent says.