Trigger Warning: A Journey through Howard Stern's Most Controversial Interviews
By Sophia Maddox | October 6, 2023
He Tried To Weigh Anna Nicole Smith
Howard Stern's name has become synonymous with shock value, and his interviews often tread a not-so-fine line between straight talk and outright audacity.
This gallery is not for the faint of heart. No, dear friends, this is a front-row ticket to the wildest, most contentious, and mind-boggling chats in radio history. Prepare yourself to cringe, gasp, and perhaps even laugh as you plunge into the belly of the beast. These are Howard Stern's most controversial interviews - brace yourselves, because discretion is definitely not Stern's virtue!
In typical Howard Stern fashion, no topic was off-limits during Anna Nicole Smith's appearance on the Howard Stern Show, and this included the model's much-discussed figure. At the height of Smith's career, she was known for her voluptuous, pin-up style beauty. But in the years leading up to her Stern appearance, she had faced cruel and relentless media scrutiny about her weight gain.
During her interview, Stern, with his characteristic blend of audacity and insensitivity, dared to go where many wouldn't. He brought out a scale and asked Smith to weigh herself live on air. It was a moment that stunned listeners and left Smith in an understandably uncomfortable position. Critics accused Stern of fat-shaming and exploiting Smith's struggles for shock value. The incident stoked a heated debate about body shaming, particularly the often harsh standards to which women in the public eye are held.
He Berated Gilda Radner Into Tears
This might have been one of the most infamous Stern moments of all time. In 1983, Gilda Radner came on The Howard Stern show as a mystery guest, and it didn't go well. Stern kept questioning her about her sex life, and was very aggressive, even when Radner was visibly uncomfortably. Eventually, she left in tears. Even Stern himself expressed regrets over the way he handled things:
Gilda Radner went running out of my studio, literally went running out of my studio… she didn’t trust me. I was being too outrageous, too in her face. And it was scary to this accomplished actress and comedian. 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.
He Said John Wayne Bobbitt's Abused Ex Was "Not That Great Looking"
For background: Lorena Bobbit was a young Ecuadorian immigrant married toJohn Wayne Bobbitt, an ex-marine. Their relationship was reported to be marred by continuous verbal, physical, and sexual abuse. Following another alleged episode of abuse in June 1993, Lorena took a kitchen knife and severed John's junk while he slept. She was charged with malicious wounding, but found not guilty.
John Wayne Bobbit was a guest interviewee on Howard Stern's New Year's Eve Special. In a particularly vile moment, Stern seemed to try to justify Bobbitt's abuse of his wife, repeating the tired trope of how if she didn't like how she treated him, she should have just left. Stern continued the interview with even nastier comments:
I don’t even buy that he was raping her...She’s not that great looking. She's got a lot of pimples, your ex-wife...no creep deserves what that psycho... did.
Stern would later help pay for Bobbitt's genital enlargement surgery.
He Asked Sarah Michelle Gellar About Her Body Hair
Leave her alone, Howard! Body hair questions are WAY off limits. Despite most people's understanding of healthy boundaries, Stern decided to push past any he has and ask Sarah Michelle Gellar about her body hair routine when she made an appearance on his show:
Are you blonde all over...you shave completely? Oy vey, You must look like a little baby when you're in bed.
Oy vey, indeed. Sometimes silence is the better option, Mr. Stern.
He Pushed Scott Weiland To Talk About His Sexual Abuse
CONTENT WARNING: SEXUAL ABUSE
Howard Stern was a big fan of Stone Temple Pilots, and their frontman Scott Weiland, who tragically passed away while on tour in 2015. However, Stern didn't act very friendly during Weiland's appearance on his show in 2011. When Weiland began opening up about the childhood sexual abuse he had experienced, saying that an older male had "made [Weiland] do things to him], Stern callously responded:
He made you suck him off?
Wow. Read the room, Howard.
In 2001, young heartthrob and all-American good guy Freddie Prinze Jr. went on Howard Stern's show to promote a movie, shortly after his engagement to now-wife Sarah Michelle Gellar. Instead of congratulating the young couple, Stern said the marriage wouldn't last, suggesting Prinze would end up cheating. He even offered to make a bet for a million dollars on the issue. Prinze didn't bat an eye, completely confident in his marriage, despite Stern's offensive implications:
Oh, absolutely it will last. We'll do a written bet. We'll do it right now.
Prinze obviously knew his marriage way better than the shock jockey did. It's been over twenty years and counting since that interview, and his love story with Sarah Michelle Gellar is still going strong.
He Said He Hoped Heather Locklear's Daughter Was Hot
How do you make a conversation about someone's baby uncomfortable? Well, turns out Howard Stern can tell you! When Heather Locklear appeared on his show, the conversation quickly turned to Locklear's four-month old daughter, and Stern made it weird with the following comments:
Having a baby did you some good... I hope she's as hot as you...How long did you and Richie [Sambora] wait to make love after the baby was born?
He also asked her about her sex life with her ex husband, among various other no-go topics. Yikes.
He Told Harry Styles He Had Daddy Issues
You might think all of Stern's "edgy" humor is from the 90's, but he's still bringing the shock to this day. In a 2020 interview with Harry Styles, he again crossed the line from personal to "Don't go there". When Styles mentioned his therapist, a woman, Stern had some strong opinions. Not only did he suggest that Styles would end up "seducing" a female therapist, he suggested that due to his daddy issues a male therapist would be more useful. How rude - both to the musician and female therapists everywhere!
Your father left, you've got some father issues. You need a strong man in your life. You need a male therapist.
Classy as ever, Styles brushed the comment off. We're not sure we could have handled it with such grace!
He Wouldn't Stop Drooling Over Mariah Carey
In a 1998 interview with Mariah Carey, the King Of All Media kept taking things too far. He told the pop diva that they were going to film up her skirt, that her breasts "were incredible", and said she dressed like a stripper. In response to the breasts comment, Carey flatly replied that they were normal breasts. Even though she appeared uncomfortable and disinterested, Stern took things a step further, asking her an inappropriate question directly?
Do you ever wear underwear, ever? Are you wearing underwear tonight?
Carey gracefully laughed the question off. A queen, as always.
He Wouldn't Shut Up About Arnie's Divorce
Arnold Schwarzenegger and Maria Shriver's separation, announced in 2011, came after 25 years of marriage. It was later revealed that the split occurred after Schwarzenegger admitted to having fathered a child with a member of their household staff. When Arnie appeared on The Howard Stern show in 2015, Stern was eager to dig into the downfall of the relationship. Though the Terminator wasn't too stoked about it, we did get a little insight into it all - including the fact that he thought his marriage counsellor was the worst:
Yes, we did [seek counselling], Maria and I, and it was the biggest mistake I've ever made. That guy was so full of ****. He said more crap and more nonsense. It was absolutely counterproductive to our future relationship... Maria talked me into it. I went, and I felt instinctively maybe I shouldn't go because I know I screwed up. I don't have to go through anyone to have to explain to me anything. I apologized to Maria. I apologized to the kids.
We feel like this breakup isn't on the therapist, Arnold!
He Got Inappropriate With Emma Bunton
Things got pretty weird in Spice Girl Emma Bunton's interview with Howard Stern. The shock jockey asked her if she was underwear, played sexual noises, and asked inappropriate messages about her personal life, such as when she first got her period and when she lost her virginity:
You weren't a virgin when you joined the band, were you? You've got a hot little body. I can see you girl-on-girl action, I can see you with two guys. I could see you doing a lot of things.
Bunton coolly replied that her dad wouldn't appreciate this line of questioning.
He Creeped On Sofia Vergara
Howard Stern seriously crossed a line in an interview with actress Sofia Vergara, even going so far as to bring her son into it. Not only did he tell Vergara that breastfeeding her son (who she had at age nineteen) must have been unbelievable, he went on to ask this distasteful, and biologically incorrect question:
You must’ve had so much milk. Right? How much milk?
Time for another science class. And perhaps a book on etiquette.
He Made Weird Comments To Courtney Love
Courtney Love is yet another victim of Howard Stern's questionable comments. When Love came on the show in 1998, she slipped off her jacket, revealing a crop top, a staple of the 90s. This, of course, prompted Stern to say the following:
Ooh yeah, you got a nice stomach. Just stand there for a second, let me look at you. Body’s hot.
Despite verbal and nonverbal cues from Love showing her discomfort, Stern just can't keep his mouth shut.
He Pulled A Mean Prank On Howie Mandel
Comedian and TV host Howie Mandel probably doesn't have the fondest memories of this encounter with Stern. In the studio, Stern and the crew decided to pull a that went as follows: Mandel, who has diagnosed OCD, noticed a man with unsanitary hands had touched a door knob, and attempted to cover the doorknob when exiting the room. When prevented by the crew, he began to panic:
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. 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.
He Put Carmen Electra On A Vibrating Chair
Actress Carmen Electra has made some very...interesting appearances on The Howard Stern Show. In one of these, back in the early 2000s, Electra decided to take a spin on a vibrating chair made specifically for intimacy, live on the air. As expected, some questioned this decision, but Electra didn't see anything wrong with it:
I thought I didn’t do anything wrong. I didn’t do anything vulgar. It was a chair. I sat on a vibrating chair.
Our question is, why did Stern already have one of these in the studio?
He Made It Seem Like Dolly Parton Said A Racial Slur
While not an interview per-se, this interaction was too crazy to not include. In 2008, Stern's team frankenspliced bits of country legend Dolly Parton's audiobook, My Life and Other Unfinished Business and manipulated it to sound like she had said a racial slur. Poor Parton was absolutely mortified:
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.
In response to Parton threatening to sue, Stern insisted it had all just been a fun bit, and "obviously parody". He never publicly apologized.
He Secretly Weighed Carnie Wilson
Musician Carnie Wilson, part of group Wilson Philips and daughter of Beach Boy Brian Wilson, had a terrible go of it on The Howard Stern Show. The Shock Jockey weighed her without her knowledge, and followed this up with insulting questions, including asking her then-fiancé why he was attracted to her, or if he was gay.
I went to do The Howard Stern Show and when he was on E!, it was on camera, so 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. I said, ‘Wait a minute?’ and I looked down and all I could think was ‘Howard, ready to shame me?’ They purposely did it. It’s like a joke to him, but it wasn’t to me. It was one of the worst experiences I ever had. I was so devastated and so embarrassed. Humiliated really. And [my husband] went down, bought me some yellow roses inside the hotel. But I literally crawled in bed.
He "Made Out" With Ellen DeGeneres
In 2019, talk show queen Ellen DeGeneres was getting some grief for getting chummy with former president George W. Bush at a ball game. Stern suggested an...unconventional idea to change up the tabloid headlines:
People were giving you grief about this George Bush picture, but listen, you know, I'm always with you. I'm on your side. The problem is—and this is a brilliant booking on your part, having me on the show—people have this picture in their mind of you and George Bush. What you need to do, in my opinion, is take a picture with me, making out with me. I'm just thinking. Once people see me with you, no one's going to be thinking about George Bush.
Hmm. Was it worth it, Ellen?
He Talked Miss America Pageants With Donald Trump
We're sure you've heard of this one. In Donald Trump's infamous 1996 interview with Howard Stern, Trump went into how he would often go backstage to "inspect" the Miss America pageants. Trump clearly meant it to be a cute, comedic story, but, as expected, many were grossed out by his audacity.
I’ll tell you the funniest is that I’ll go backstage before a show and everyone’s getting dressed. No men are anywhere, and I’m allowed to go in, because I’m the owner of the pageant and therefore I’m inspecting it. … ‘Is everyone OK?’ You know, they’re standing there with no clothes. ‘Is everybody OK?’ And you see these incredible-looking women, and so I sort of get away with things like that.
He Pushed Pam Anderson To Talk About The Tape
When bombshell Pamela Anderson came on The Howard Stern show, the host got to really learn about the fallout from the tape Anderson made with Tommy Lee Jones - fallout that is still reverberating today, thanks to the renewed interest the Pam & Tommy miniseries ignited.
[The tape] wasn’t a positive thing. It definitely took its toll on the relationship, it took its toll on my career, and people are still capitalizing off that. I felt kind of run over with [the Pam & Tommy miniseries]. I don’t think they really portrayed Tommy or [me] positively … I’ve only heard that it was a very shallow kind of representation of us at that time … I wish they would have called.
He Talked Wardrobe Malfunctions With Lady Gaga
In a surprising turn of events, in Lady Gaga's 2016 appearance on The Howard Stern Show, the host asked her how to keep her undies on. The pop star went on to explain that her stylist has an interesting system to prevent any wardrobe malfunctions, which, though unconventional, is foolproof:
He will sometimes glue my underwear to my...you know what...without me even asking. Brandon, he's getting me ready, and he never can watch when I go out because he's so afraid something's going to pop out... He didn't tell me. He just did it.
He Asked William Shatner Why Everyone Hates Him
During a 2008 interview, Stern broadcasted a notorious soundbite of actor William Shatner deriding a director during a voice-over session. While Stern clearly found Shatner's antics amusing, Shatner himself conceded that his actions may have been excessive. Stern proceeded to bring up the widely held notion that several of Shatner's former Star Trek colleagues ''hated' him, and asked him if they had received similar treatment to the director in that audio clip. He also asked Shatner if he thought he was "an angry man". Shatner, introspective, said he probably was:
Looking back I may have [mistreated people], it was terrible of me. I took that too far and I very well may be guilty of all this... I probably was a very angry man.
He Got Way Too Personal With Robert Downey Jr.
In 2010, Iron Man himself called into Howard's show, and Stern responded by asking him about his sex life with his wife. Fortunately, neither Robert Downey Jr. nor his wife, Susan, were phased. Downey actually handed the phone to his wife, who answered the question of how many times a week they get intimate:
If we’re on vacation, two or three.
That solves that mystery!
He Brought Up THAT Donald Trump Photo With Kathy Griffin
Griffin, an acclaimed comedienne known for her sharp tongue and no-holds-barred humor, found herself in hot water in 2017 when she posed for a photo holding a prop that looked like the severed head of then-president Donald Trump. The backlash was immediate and immense, leading to lost gigs, a federal investigation, and even death threats. Howard Stern invited Griffin onto his show for a no-topic-off-limits conversation. During the interview, they delved into the fallout from the photo incident, exploring the personal and professional consequences Griffin faced:
My whole life has changed since I’ve seen you. It didn’t occur to anyone that people would take it so seriously. This kind of imagery is not new to comedy. You may have hated that picture and that’s fine, but I want everyone to know if you’ve got a 13 year-old kid and they put that picture on Twitter, they shouldn’t have to be under a two-month federal investigation. That photo, as you know, is completely covered by the First Amendment.
He Talked Trauma With Stephen Colbert
We all know and love Stephen Colbert, but some may not be familiar with his tragic backstory. At age 10, Stephen lost his father and 2 brothers in the infamous disaster of Eastern Air Lines Flight 212. This catastrophe was instrumental in implementing the Sterile Cockpit Rule, as the flight's black box recorder revealed that the pilots had been distracted by discussing politics and an amusement park, among other unrelated topics.
Understandably, this devastating event had a painful and lasting impact on Colbert and his surviving family members. Stern took the time to explore these feelings in a 2015 interview:
It’s built into me the way like, the marble is built into the shape of a statue … It’s kind of, at a certain age, what I was made of.
He Told Jon Stewart To Run For President
In 2023, Howard Stern made it clear that he wanted former Daily Show host Jon Stewart to run for the position of U.S. President - and that he had Stern's vote:
Over vacation, I’m watching a ton of this one guy, and I’m watching him debate all kinds of different people. He knew more than any of them. The guy is so ******* smart and bright and also witty and really measured when he takes on a debate. He knows how to talk. You know he would work his ass off to be a good president. I’m telling you, he could also win, because people like Jon Stewart.
What do you think? Would you vote Jon Stewart for 2024?
He Asked Conan O' Brien About His Depression
In a 2015 interview, Howard Stern got everyone's favorite TV host Conan O'Brien to open up about his depression, which he had struggled with for years:
You know, man…I really think no one likes me, I think people hate me, I think people think I’m not good at what I do, and I think people want me to go away...Listen, these are voices in your head, okay? We all have those negative feelings, but they’re just feelings – they’re not real.
He Told Emily Blunt That Her Ex Was Perfect For Her
In an odd move, Stern told actress Emily Blunt that her ex, Michael Bublé, was perfect for her...while trying to get her to discuss his infidelity only moments later. Luckily, the actress didn't take the bait, and kept things simple and sweet:
I don't know if I was perfect with him. We had a good time together. I loved his family, I still do. I don't know, it's complicated. Now I'm going red...I never talk about it. I never want to talk about it!
Blunt has been married to fellow actor John Krasinski since 2010, with whom she shares two daughters.
He Bullied Jerry Seinfeld with Gilbert Gottfried
The late Gilbert Gottfried was a frequent visitor to the Howard Stern show. On one memorable occasion, the two teamed up to practice their Jerry Seinfeld impressions on air, and then proceeded to leave an almost half-hour long voicemail on the actor's answering machine - as Jerry Seinfeld. We're sure Seinfeld wasn't too pleased!
Interviewing Robin Williams Was His Biggest Regret
Back in the '90s, the King of All Media scored an interview with the late great Robin Williams, but things didn't go as planned. Although Stern was a big fan, he decided to get too personal, too fast, rather than focusing on more intellectual conversation:
I was a baby. I want every listener. I want everyone focused on me. You’re not going to be funnier than me. You’re not going to come into my studio and steal the moment from me. This is who I was...I loved Robin Williams, but there I am beating him over the head with, like, ‘Hey, I hear you’re ******* your nanny?’ I could have had a great conversation, but I’m playing to the audience. They want to hear outrageousness, and that’s my arrogance thinking that Robin Williams can’t entertain my audience. How stupid am I?
Stern cites this interview as the one he wishes he could go back in time and re-do.