The Most Outrageous Celebrity Confessions On Howard Stern

Howard Stern, the undisputed shock jock king, has cemented his place as a radio legend over the course of a long and controversial career that included a 20-year run at WXRK in New York City. Free from the shackles of censors since his move to SiriusXM, his infamous on-air interviews tend to go off the rails at any moment. Stern has perfected the art of making his guests feel relaxed and prompting them to share very personal stories. In fact, Stern's guests often find themselves answering salacious questions that would never fly in most interviews, and some celebrities straight-up volunteer show-stopping information with him that they may regret later.

From Lady Gaga going deep into her drug-addicted past, to Nick Cannon opening the doors of his bedroom with Mariah Carey, and Robert Downey Jr. brutally slamming a reporter who took things too far, here are some of the most outrageous and shocking celebrity confessions uttered on The Howard Stern Show.

Jada Pinkett Smith and Will Smith have long been one of Hollywood's most respected and beloved couples. They've been married for more than two decades and share two kids together and Will's son from a previous marriage. Despite their positive family image, Jada and Will have been shadowed by rumors of an open marriage. The Baltimore-born actress took to Stern's show in 2015 to set the record straight.

"You've got to trust who you're with," she told Stern. "And at the end of the day, I'm not here to be anybody's watcher. I'm not [Will's] watcher." So what does that mean? "Here is what's real: I'm not the kind of woman that believes a man is not going to be attracted to other women," she said. "I'm just not that girl. It's just not realistic. And just because your man is attracted to another woman, does not mean he doesn't love you." That confession, of course, did nothing to quiet the gossip about this power couple.

Madonna's dating history includes a lengthy list of well-known men such as Sean Penn, Guy Ritchie, and even Vanilla Ice, but during a show-stopping interview in 2015, the "Material Girl" dropped a dating bomb that threw the internet into a tizzy. She revealed a romantic relationship with the late rapper Tupac Shakur.

The news emerged as Stern was grilling Madonna about her infamous, profanity-laced 1994 interview with David Letterman. "I don't know, I was in a weird mood that day," Madonna said. "I was dating Tupac Shakur at the time, and the thing is he got me all riled up about life in general. So when I went on the show I was feeling very gangster." 

That explanation caught Stern and co-host Robin Quivers totally off guard. "That's shocking to me," Stern said. "That's never been out there, I don't think."

In 2016, a 50-year-old Ben Stiller revealed that he was diagnosed with and treated for prostate cancer at age 48. He opened up about his health drama with Stern, saying that he owes his life to a controversial test that is generally not given to patients until after age 50. He began testing at age 46, underwent surgery, and is cancer free to date.

Because Stern is not one to shy away from very private questions, he asked Stiller if removing the prostate affected the actor's ability to perform with this wife, actress Christine Taylor. "It takes time to come back," Stiller replied. "It changes the experience of what an orgasm feels like. It's great, it just feels different."

After being given a clean bill of health, Stiller's life perspective changed. "It just gives you an appreciation in life and all the other bullsh*t doesn't matter," he said.

Nick Cannon shouldn't kiss and tell. In 2012, four years before their divorce was finalized, Cannon opened the door to his and Mariah Carey's bedroom to the entire world. Cannon, who shares twins with Carey, claims they didn't become intimate until after they exchanged vows in 2008. "I knew what her values were," he dished to Stern (via the Daily Mail), noting they simply "made out" before tying the knot. Cannon added that he wasn't concerned about his wife's skills in the bedroom before marrying her. "It was Mariah Carey," he quipped. "If Mariah Carey gave a bad bl**job, I'm still going in. Either way she's still one of the most beautiful women on the planet."

Things took an uncomfortable turn when the conversation switched to masturbation. Cannon confessed to pleasuring himself to Carey's music when they were apart. "Why not?" Cannon laughed. "I light candles. Sometimes you've got to be reminded of what's at home." His choice of song to set the mood? "Hero."

Reality star Jesse James once again showed his true colors on Howard Stern's show. James was married to Oscar-winning actress Sandra Bullock from 2005 to 2010. Their union came to a dramatic and rather public halt after news broke about his cheating ways. Fast-forward to 2011: James apparently felt the need to embarrass Bullock further by comparing sex with his ex to romps with his new lady, tattoo artist Kat Von D. When Stern asked him who was better in bed, James replied (via the Daily Mail): "That one is an easy no-brainer. One hundred percent. {Von D is] a vixen." 

James even confessed that he wanted Bullock to find out about his affairs. "I think I subconsciously did want to get caught, but I didn't think it would be as crazy as it got," he said. James said his insecurities in their highly publicized romance contributed to his infidelity. "The problem was me ... I could marry anyone and it didn't matter because I would always screw it up and sabotage it because I couldn't live with myself," he said. "She could stand there in front of the world and say she loved me, but in my mind I was thinking, 'Yeah? Bulls**t. You don't love me. I'm just some biker kid.'"

Looking back, James wishes he was a bigger man. In fact, he wishes he ended his marriage instead of embarrassing Bullock. "I should have done the honorable thing and just left her," he added. "Because I did really love her and I did really care for her."

One may not want to burn the bridge that gave you success. Just ask Channing Tatum. In 2015, the actor bashed the studio that gave him a three-picture movie deal. The star of 21 Jump Street and Magic Mike slammed his role in the 2009 film G.I. Joe: The Rise of the Cobra.

"Look, I'll be honest. I f**king hated that movie," Tatum told Stern. "I was pushed into doing that movie .... They give you the contract and they go, 'Three-picture deal, here you go.' And as a young [actor], you're like, 'Oh my god, that sounds amazing, I'm doing that!'" Tatum was brutally honest when he described the quality of the project. "The script wasn't any good," he said, adding, "I just didn't know if I wanted to be G.I. Joe."

Tatum assessment of Stephen Sommers' project apparently wasn't wrong. The blockbuster was sort of a bust. According to Box Office Mojo, it earned only $150 million in theaters nationwide on a $175 million budget, but it did pick up another $302 million worldwide.

Wilmer Valderrama is another one of those Hollywood bros who just can't seem to keep his mouth shut about the women he's slept with over the years. In one of the most infamously tacky interviews of all time, Valderrama sat down with Stern in 2006 and prattled off his list of conquests: Jennifer Love Hewitt, Lindsay Lohan, Jessica Alba, Jaime Pressly, Rosario Dawson, Ashlee Simpson. The most shocking revelation came when Valderrama claimed that he "snatched" Mandy Moore's virginity. 

The couple famously dated from 2000 to 2002, while Valderrama was on That 70s Show and Moore was at the top of the pop charts. "We were each other's first loves," Valderrama said before crudely describing the experience as "not like warm apple pie."

In 2016, Valderrama started dating Moore's BFF, actress Minka Kelly. When asked about potential awkwardness on an episode of Watch What Happens Live, Moore said the situation was "not weird" and that she loves them both. "We're like very, very close friends," she continued. "[We dated] for a year — he was my first boyfriend when I was 15. We can still be friends!" (Maybe Moore didn't tune in to Stern's show.)

After winning the Tour de France a record seven consecutive times from 1999 to 2005, cyclist Lance Armstrong was a living American icon before an illegal doping scandal brought it all crashing down. Denying the charges and allegations against him for years, Armstrong agreed to a 2013 interview with Oprah Winfrey and finally admitted to using banned performance-enhancing drugs throughout his racing career. What does this have to do with Howard Stern?

In 2017, Armstrong sat down with Stern to finally reveal why he decided to come clean with Oprah and, by extension, the whole world. That interview made waves too. "It was too soon for a lot of people and too detailed and too shocking for a lot of people," the cyclist said, noting that he trusted Winfrey. "I knew I was going to get sued," Armstrong said. "When the report came out and they [stripped] the titles, I f**king knew they were lining up." 

After only knowing each other for a year, Fred Armisen married Elisabeth Moss in 2009, only for the pair to call it quits eight months later. Describing the experience as "extremely traumatic and awful," The Handmaid's Tale star has opened up to several publications since then with her blunt assessment of where the blame should lie for the demise of their relationship. In a particularly harrowing 2012 interview with Page Six (via The Huffington Post), Moss held nothing back. "One of the greatest things I heard someone say about [Armisen] is, 'He's so great at doing impersonations. But the greatest impersonation he does is that of a normal person.' To me, that sums it up." Yikes!

Naturally, when Armisen sat down with Stern a year later, that topic came up. "I was a terrible husband," the Portlandia co-creator and former SNL staple freely admitted. "I want it all — fast ... I want to be married," he continued. "The amount of girls I've lived with — right away — and then somewhere around a year, two years, I get freaked out. Freaked out emotionally ... and I actually feel like, 'oh my god, who is this stranger in my house?'"

A lot has happened to Matt Lauer since 2013, but in the summer of that year, the former Today show personality stopped by Stern's SiriusXM studio and opened up about his relationship with Katie Couric, his co-anchor from 1994 to 2006. Couric confessed to having a "little crush" on Lauer during an earlier appearance on Stern, so naturally, this became a hot topic of discussion. 

"I think ... every man in America was attracted [to Katie Couric]," Lauer said (via Us Weekly). "She's a very attractive woman, not only physically, but her personality ... if she's a 9 or 10 physically, she's a 14 because ... She's fun." Lauer said he never pursued a romantic relationship with his coworker but made the outrageous boast that if he had, Couric would not have been able to resist his charms. "She would have been knocking on my door constantly," he said. "She would have never left me alone."

In a conscientious interview with Britain's Channel 4 reporter Krishnan Guru-Murthy to promote Avengers: Age of Ultron, Robert Downey Jr. quickly found himself ambushed with questions about his past struggles with drug abuse. It didn't go well. With a simple "bye," Downey got up and walked out. The man who launched Marvel's billion-dollar franchise appeared on Howard Stern in 2015 to give his unfiltered thoughts on the ordeal, and boy, did he. 

"I'm one of the guys who is always assuming the social, kind of decorum is in play, and that we're promoting a superhero movie — a lot of kids are going to see it — and this has nothing to do with your creepy, dark agenda. I just realized, too, that I'm a 50-year-old guy, I use fancy words on The Howard Stern Show, and yet I'm completely unevolved when it comes down to simple boundaries. Like, you know what? You're weirding me out. You are a bottom-feeding muckraker." 

"What I have to do in the future is just have to give myself permission to say, 'that is more than likely a syphilitic parasite, and I need to distance myself from this clown,'" Downey said. "Otherwise, I'm probably gonna put hands on somebody, and then there's a real story." 

Note to self: use "syphilitic parasite" more in everyday conversation.

James Franco always finds a way to go full James Franco, and in 2014, he allegedly tried to hook up with a 17-year-old girl on Instagram. The girl, Lucy, a Scottish tourist in NYC for her birthday, met the then 36-year-old Franco after attending his Broadway show, Of Mice and Men. She took an Instagram video with him, and he told her, "You gotta tag me." Apparently, he then wasted no time trying to get in her pants. A month later, Franco went on Howard Stern's SiriusXM radio show and defended his slide into her DMs because teenagers are part of his "fan base." 

"I'm not going to high schools looking for dates. I'm leaving my work and they're coming there," Franco told Stern (via Bustle). "If I do a book signing, it'll be 17-year-old to 30-year-old women. That's my biggest fan base. So I saw her, and she's saying on her page, 'I love James Franco,' blah blah blah... So that, to me, sounds like, okay, she's interested." 

Nope. Not creepy at all. 

Lady Gaga is known for baring every element of her soul in her music; whether it's talking about depression, abuse or political rights, she's an open book. During a 2011 interview with Stern, the pop star came clean about heavy drug use in her past. "I was so unhappy," she told Stern (via E! News). "I think that I was lonely and there was something about the drugs that made me feel like I had a friend ... I didn't do it with other people. I did it alone." Gaga says she became creative during that time: "I did it all alone in my apartment and I wrote music and you know what, I regret every line I ever did. So to any of the little sweethearts that are listening, don't touch it, it's the devil." 

In true Stern fashion, he turned the conversation toward sex. Gaga confessed to a "brief" foray into same-sex experimentation, while also urging girls to guard their virginity. "Honestly you should wait as long as you can to have sex, because as a woman you don't even begin to enjoy it until your mid-twenties," she said. "When you're 17, you don't even know how to operate what's going on down there and you shouldn't try."