11 Times Howard Stern Made Celebs Uncomfortable

Howard Stern became a household name thanks to his reputation as the long-running radio show host of "The Howard Stern Show." In 2006, Stern's popular program transferred from traditional radio to Sirius XM, a move that made him one of the highest-paid radio figures ever when he signed a five-year deal worth $500 million. The host has remained on Sirius XM ever since, thanks to his legions of fans. But occasionally, the celebrities who come on his show don't leave with that same adoration. 

Stern's offensive questions and oftentimes shocking persona have scared off fellow hosts. David Letterman reflected on the time he worked in the same building as Stern on "Jimmy Kimmel Live," sharing, "In those days, Howard was 'shock jock Howard,' and I was always afraid of Howard. Because I didn't want Howard to say unpleasant things about me — but he did. And I kept thinking to myself: He must not have any feelings of his own because he would say hurtful things, and the more hurtful things he would say, the greater his audience would become, so I just thought, I'm in the wrong business here." 

Eventually, the two hosts would become friends, but Letterman's worries are a testament to the type of show Stern has been known for. Let's explore the celebrities Stern has made uncomfortable in the hot seat.

Emma Bunton was on the firing end of some of Howard Stern's most inappropriate questions ever. The "Spice Girls" member stopped by the show in 2005 and was subject to inquiries that would never fly in today's world. Stern kicked things off with obscene questions about whether or not Bunton was wearing a bra and underwear. The singer awkwardly laughed, replying, "I knew that you were gonna say that." Though she clearly didn't love the sexual topics, he forged on with more rude questions.

"You weren't a virgin when you joined the band, were you?" Stern asked, and when Bunton shared that she was, he asked if she was lying. Stern continued this horrific line of conversation by speaking about Bunton in sexually inappropriate ways. One of Stern's team members didn't help matters, adding, "If your father's the milkman, you gotta put out." Bunton was seemingly not pleased with the topics and responded, "My dad won't be happy that you're talking to me that way."

Sadly, that wasn't the end of the disgusting questions. Stern also asked Bunton about her development as a teenager, and she looked increasingly uncomfortable. Stern played gross sexual sounds to the point where Bunton removed her headphones to stop listening.

Freddie Prinze Jr. stopped by "The Howard Stern Show" back in 2000, and he was subject to some very uncomfortable inquiries about his relationship with Sarah Michelle Gellar. The host brought up sexual topics early in the interview. Stern asked Prinze, "She's a good little piece of a** though, right? ... I need some of that, when you're done with her I'll get her." He further asked, "Is she the best piece of a** you've ever had?"  Prinze smiled through these atrocious questions, deflecting by answering, "She's an amazing, amazing, amazing woman."

Stern continued to make inappropriate comments about Prinze's girlfriend, asking a minute later, "Does she have good boobs? It looked like it was sagging down a little bit." Still, Prinze returned to the show in 2001 to talk to Stern... this time about the duration of his relationship with Gellar. 

Adamant that the relationship would not last, Stern demanded to make a bet that the couple wouldn't be together more than ten years, telling Prinze, "Put your money where your mouth is." Stern owes the actor that million dollars — Gellar and Prinze went on to marry the next year, in 2002, and are still together two decades later. In April 2022, the couple posted screenshots from the interview on their Instagram Stories (via HuffPost), tagging Stern and writing, "I think you owe us." 

Though they eventually became friends and co-workers, both serving as judges on "America's Got Talent" beginning in 2012, Howie Mandel and Howard Stern had a rocky past. In 2006, Mandel stopped by Stern's show. The comedian recounted that painful experience in 2021 on the podcast "Inside of You with Michael Rosenbaum."

Stern's crew decided to pull a prank on his guest. Mandel noticed that a man who had been touching his penis had then touched the doorknob. Stern asked someone else to open the door, and no one would. "And I went to grab a tissue to grab the door and they knocked the tissue away from me, and I was trying to pull up my shirttail, and they were holding me from that." Mandel had a panic attack during this harassment. When speaking to the OC Register in 2018, the "Deal or No Deal" host remembered, "I started to hyperventilate and blurted out, 'Howard, I go to a psychiatrist and have obsessive compulsive disorder and you have to open the door or I'm going to pass out.' And then they opened the door." 

Mandel then discovered that the ordeal was being broadcast live and his confession was public knowledge. The actor was mortified and feared that his family would be embarrassed. After leaving in a panic, he was planning to end his life. However, someone approached Mandel on the street and shared that they also had mental health struggles. Suddenly, Mandel knew that he was not alone, and that he had helped someone.

If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline​ by dialing 988 or by calling 1-800-273-TALK (8255)​.

Heather Locklear's 1998 interview on "The Howard Stern Show" was doomed from the beginning. Stern kicked things off before she even stepped into the studio by saying, "I hope she's wearing a dress, man. I hope she's wearing a short little dress." Though she was wearing pants, Stern still managed to make an uncomfortable comment upon seeing her, stating, "Having a baby did you some good."

In a conversation focused on her four month-old daughter, Stern made such an inappropriate comment about the baby: "I hope she's as hot as you." He also inquired about Locklear's postpartum activities, asking, "How long did you and Richie [Sambora] wait to make love after the baby was born?" The actor, who clearly wasn't too enthused with the question, said she didn't remember. 

Other uncomfortable topics he presented the star with during the interview? Talking endlessly about the size of ex-husband Tommy Lee's manhood and asking if she had seen his sex tape with then-wife Pamela Anderson, asking if Locklear would let husband Richie Sambora watch her go to the bathroom, and asking some racist questions about the nationality of her daughter's nanny. 

According to the Mirror, a TikTok poster has called this next case one where the interviewer crossed a line. The late Anna Nicole Smith was a frequent guest on "The Howard Stern Show," but it was a 2002 appearance where Stern really went overboard. Before the model-turned-reality star even entered the studio, Stern was talking negatively about her weight, stating, "...Anna doesn't recognize that she's a big girl and maybe shouldn't wear belly shirts." He seemed to have an obsession with her weight and even got everyone on the crew to take bets on how much the model weighed. 

Smith, who had been listening before going into the interview, arrived visibly upset. Things only got worse as Stern tried to ask questions about her late ex-husband, to which Smith said, "I'm not gonna answer any more questions about my husband... I'm not gonna talk about my husband and get me upset." He also asked why Anna seemed "out of it" on her reality show, after saying he thought she was on drugs. Stern requesting that Smith get on a scale live on camera didn't fare much better. Smith declined, despite Stern trying to bribe her. "I think you should be proud of what you weigh," Stern goaded the late star, who continuously refused to get on the scale and looked upset from the pressure.

For those claiming Howard Stern's most offensive interviews took place decades ago, he's just as offensive today. Somehow he has managed not to be canceled in current society. While he's tamed his interviewing tactics, the shock jock still makes his guests uncomfortable. Take his 2020 interview with Harry Styles, for example.

After discussing Styles' love life, Stern awkwardly suggested that the pop star should see a therapist. That inappropriate comment prompted Styles to explain that he was seeing a Los Angeles-based therapist. "I worry about you going to a woman therapist," Stern said, taking things further. "You're gonna f***ing seduce her." 

Aside from not letting go of his theory that Styles was going to be intimate with his therapist, Stern made another bold assumption about the star: "Your father left, you've got some father issues. You need a strong man in your life. You need a male therapist." Styles made light of the comment, asking Stern, "You stepping up?" But overall, the whole thing was awkward, and Styles would probably rather not sit through such absurd interrogations.

In 1998, Mariah Carey stopped by "The Howard Stern Show" and was in for a slimy Stern surprise. Carey asked what kind of shots the camera would be getting, to which Howard Stern responded, "Right up your dress!" The superstar singer was prepared for the host's bag of tricks. She said, "I'm not sure about what's going on, and you guys can be a little bit lewd sometimes." Indeed, Stern got more and more lewd, asking her, "Why didn't you flash me onstage?"  He then drew attention to her breasts. 

Carey brought up prior mean comments Stern made on his show, told him not to be lewd with her, and emphasizing that she was an "innocent girl," but Stern's line of questioning remained the same. "Do you ever wear underwear, ever? Are you wearing underwear tonight?" Stern asked a flustered Carey, to which the singer responded, "Howard, you think I'm going to go with this without panties. Who do you think I am?" 

Carey eventually got angry at the shock jock when he kept discussing how she loved to show off her body. The artist frustratedly stated, "Howard, don't say that. You're making a mockery of me." "You dress like a stripper," Stern later said, leading Carey to (somewhat) jokingly suggest this interview would be cut short.

Emily Blunt stopped by "The Howard Stern Show" in 2015, where she was awkwardly barraged with questions about her famous ex. The British actor famously dated singer Michael Buble from 2005 until 2008, when he was alleged unfaithful, and Howard Stern decided to bring up the demise of her relationship during their interview. 

"I didn't realize you were in a deep, heavy relationship with Michael Buble," Stern said (via ET), then uncomfortably asserting that the stars were a perfect couple together. The host also brought up the personal detail that Buble took her home to meet his mother before stating, "He was not faithful." 

This baited Blunt into discussing the infidelity. The actor reluctantly entertained the accusation, responding, "Well... I don't know if it was... I don't know. It's complicated. Now I'm going red." Stern asked why she was turning red, and Blunt replied, "Because I never talk about it. ... I never want to talk about it." The host then offered to help her seek closure by having her imagine that he was Buble, though Blunt declined the odd suggestion.

The late Gilda Radner's 1983 appearance on "The Howard Stern Show" might be one of the most painful interactions to date. Radner arrived as a mystery guest and promptly announced, "It's really dumb here," prior to starting the interview, which only unraveled from there. Both Stern and co-host Robin Quivers continuously asked Radner to disguise her voice.

Once Radner's identity was revealed, callers asked questions about sexual topics that the actor increasingly seemed uncomfortable with, until Stern seemed to curtly put an end to the segment. "I thought you'd really like me. Did you have fun?" Stern asked at the end, to which Radner replied before leaving, "No. It was pretty scary." Stern reminisced about the cringeworthy interview on "Larry King Live" in 2006, offering it up when asked by King who his worst ever guest was. After naming Radner, Stern said, "She came in, I guess she had heard I was insane. And she came in and she was very shaky and kept, sort of getting up and she got up quick to leave and hit her head on a speaker. And she was just, it was a disaster."

He completely changed his tune by 2019. That year, the shock jock stopped by "The Late Show with Stephen Colbert" and claimed he regretted the infamous Radner interview, sharing, "Gilda Radner went running out of my studio... I was being too outrageous, too in her face... I came on like a bull in a china shop and it was wrong to do because it didn't lead to anything real, it didn't lead to good conversation." 

Remember when Howard Stern tried to lure Anna Nicole Smith onto a scale as his crew took bets on how much the reality star weighed? Well, back in 1999 he did something even worse to Carnie Wilson. According to ET, Wilson appeared on "The Talk" in 2017 and recounted her humiliating time on "The Howard Stern Show."

"When I walked in, the producer Gary said, 'Step over here and wait for Howard.' Well I didn't know this, but I was stepping on a scale. And I looked up and in red, big numbers, 233 lbs. showed up on this thing," Wilson shared with the ladies of "The Talk." In the actual interview, Stern derided her appearance, criticized her weight, and asked how her then-fiance (now husband) was interested in her.

Unlike some guests, Wilson wouldn't stand for the abuse. She recalled, "I gave it back to him. I said, 'This man really loves me, and that scale can just [go screw].' And he said, 'You know what, I adore you.'" Despite Stern seemingly respecting her for fighting back, Wilson didn't look back on the interview fondly. "It was one of the worst experiences I ever had. I was so devastated and so embarrassed. Humiliated really. And Rob [Bonfiglio] went down, bought me some yellow roses inside the hotel. But I literally crawled in bed," said Wilson. Stern's historic fixation on his guests' weight is appalling, and he told The New York Times Magazine that concern for his wife and daughter led him to make changes.

Dolly Parton didn't even have to sit in the hot seat on "The Howard Stern Show" to be offended. The iconic country star was subject to an attack on Stern's controversial radio show without stepping foot in the studio back in 2008. According to the Daily News, Stern's team chopped up Parton's voice from one of her audiobook recordings to make it sound like she was describing sexual vulgarities and pedophilia, also using a racial slur. The slanderous edit was reportedly over three minutes long.

Parton put out a statement at the time, denouncing the stunt. It read in part, "I have never been so shocked, hurt and humiliated in all my life. I cannot believe what Howard Stern has done to me. In a blue million years, I would never have such vulgar things come out of my mouth. They have done editing or some sort of trickery to make this horrible, horrible thing. Please accept my apology for them and certainly know I had nothing to do with this" (via Billboard).

She threatened to file a lawsuit, and Stern wasn't amused at the prospect. Stern allegedly defended his decision to manipulate the sound bites, saying, "It's an absurd bit. It's obviously parody and it's funny as hell" (according to The Boot). He said of the proposed lawsuit, "I can't even imagine someone thinking they have an actionable case, but bring it on."