The Most Uncomfortable Howard Stern Interviews Ever

Howard Stern, who served as the host of the nationally syndicated The Howard Stern Show between 1986 and 2005, earned himself a reputation as one of the most outspoken figures in radio history. Featuring a rotating cast of supporting guests, in-depth celebrity interviews, and multiple outrageous on-air moments that resulted in record-setting fines from the Federal Communications Commission, Stern's show marked him as someone who wouldn't hesitate to repeatedly cross the line. Stern and his show moved over to Sirius XM in 2006, and he also served as a judge on America's Got Talent between 2012 and 2015 (displaying a markedly more subdued persona). 

Over the years, Stern's celebrity interviews, in particular, have made headlines as a result of the manner in which he's able to coax famous folks to discuss personal details that they'd otherwise likely keep private (at least if it were up to their publicists). In 2016, the New York Times called him "one of the most deft and engrossing celebrity interviewers in the business and a sought-after stop for stars selling a movie or setting the record straight." But not all of Stern's searing interviews have gone well. The following rank as some of the most uncomfortable and cringeworthy ever aired. 

Although, according to the New York Times, Girls creator Lena Dunham once called Stern an "outspoken feminist," he took a decidedly sexist approach to a 2005 interview with Emma Bunton, aka Baby Spice of the Spice Girls. In a clip that Metro UK brought back to light in October 2017, Stern bombarded Bunton with invasive questions about if she was wearing underwear, when she lost her virginity ("You weren't a virgin when you joined the band, were you? Were you really? ... No kidding, at 18? Are you lying?"), and when she hit puberty. "You were very developed. What age did you develop? 14?" he asked. "When did you get your period? How old were you? That's what everyone talks about." It's uncomfortable and, in a word, gross.

Perhaps most egregiously, Stern at one point accused Bunton of dressing scantily for attention, saying, "So don't act like you don't like this, you're all about this. You want attention through your body. You want it. You're asking for it, you're gonna get it," and playing sound clips from adult films. An obviously uncomfortable Bunton tried to diffuse the situation by politely answering Stern's questions and playing along, though she did protest, "My dad won't be happy that you're talking to me like this." Needless to say, this strained interview does not age well. 

In 1983, Stern had comedian Gilda Radner on his radio show as a "mystery guest" for an interview. The gag quickly got off to an uncomfortable start with Radner saying, "It's dumb here." And it all went downhill from there. Stern and cohost Robin Quivers accused Radner of "ruining the show" because she didn't disguise her voice, and an extremely awkward interview ensued in which Stern pressed an audibly nervous Radner on her personal relationships and sex life. "Did you have fun?" Stern asked at the end of the interview. "No," Radner meekly replied.

Stern later told Larry King on Larry King Live in 2006, "Gilda Radner was really freaked out by me ... 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 explained to Playboy that Radner was "one of [his] all-time weird guests," explaining, "She got weird on me and started crying and s**t."

Donald Trump was a frequent guest on Howard Stern's radio show in the 1990s and 2000s, back before he was president, and nearly every interview he did with Stern contained some kind of seriously cringeworthy moment. In September 2017, the Chicago Tribune reported on an unearthed clip from 1997 in which Trump said he could have "nailed" Princess Diana (who had recently died in a car accident) and joked around with Stern about demanding that the British royal get tested for HIV first. 

CNN Money pulled together a collection of "highlights" from Trump's interviews with Stern over the years, including his agreement with Stern's 2004 assessment that his own daughter Ivanka is "a piece of a**," Trump's assertion in 2004 that for women the age of 35 is called "check-out time," and, in 2005, Trump's description of how, as the judge of the Miss Universe pageant, he would go backstage while contestants were nude to "inspect." 

The Daily Beast also reported that during a 2003 interview Trump told Stern about being floored by a 12-year-old Paris Hilton. "The first time I saw her she walked into the room and I said, 'Who the hell is that?' At 12, I wasn't interested ... but she was beautiful," he said. And he forced Stern's intern Julie to come into the studio so he could comment on her appearance. Yikes.

Director Quentin Tarantino made headlines in February 2018 when a damning Nov. 19, 2003 interview with Stern came back to haunt him. Tarantino, who had previously come under fire for his treatment of actress Uma Thurman during filming of Kill Bill, can be heard on the audio (via Jezebel) defending director Roman Polanski, who has stood accused of drugging and raping a 13 year-old girl since 1977. 

During the interview, Stern asked Tarantino, "How come Hollywood embraces this mad man, this director who raped a 13-year-old?" Tarantino responded with a seriously out of touch POV: "He didn't rape a 13-year-old. It was statutory rape ... he had sex with a minor. That's not rape ... She wanted to have it and dated the guy ... Look, she was down with this." Just, no. 

Polanski's victim, Samantha Geimer, came forward on Feb. 6, 2018, after the audio resurfaced in the press, telling the New York Daily News, "[Tarantino] was wrong. I bet he knows it."

Indeed. Tarantino released a statement of apology to Indiewire the day after Geimer's comments, saying, "I want to publicly apologize to Samantha Geimer for my cavalier remarks on 'The Howard Stern Show' speculating about her and the crime that was committed against her. Fifteen years later, I realize how wrong I was. Ms. Geimer WAS raped by Roman Polanski. When Howard brought up Polanski, I incorrectly played devil's advocate in the debate for the sake of being provocative."

In October 2013, an obviously inebriated David Arquette called in to The Howard Stern Show and gave an interview that might be best described as discombobulated. Arquette, who had been attending a wrap party for his film The Key, told Stern, "I'm wasted." He then proceeded to embark on a half hour rant, as E! News described, discussing how the video game Grand Theft Auto V was too violent and that the only game he wanted to win was "the game of love." 

All this talk led to an extremely uncomfortable diatribe about Adolf Hitler, in which Arquette explained, "This is the most controversial thing I'm going to say. It's very controversial, and I'm sorry ... Hitler played the game very well. He did. Listen, yeah, he played his game very well. He convinced a lot of people to play his f***ing evil game. He played the game really well, but he was playing the wrong game." OMG. 

Radar Online reported in 2015 that a drunk Arquette called in yet again for another uncomfortable moment with Stern, in which he berated Stern for going to dinner with Arquette's ex-wife, Courteney Cox. According to the site, Arquette yelled, "I thought you were a friend, you f***ing a**hole! ... When you come to L.A., you don't call me, you call her?" Stern finally ended the interview by saying he felt he shouldn't speak with Arquette anymore. However, Arquette and Stern later made up in October 2015. 

Howie Mandel and Howard Stern became coworkers as co-judges of America's Got Talent in 2012, and, by all accounts, it seems like the two get along just fine nowadays. But in 2006, an interview between the two caused a lot of discomfort — for Mandel, in particular. 

As the Orange County Register explained in January 2018, at the end of the interview, Stern's crew thought it would be funny to take away all the tissues so that Mandel, who suffers from Obsessive Compulsive Disorder (OCD), would be forced to touch the studio's doorknobs. Mandel told the paper, "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.'" Mandel then realized that he was still on air. Finally, staff opened the door for him, and he ran onto the street in an embarrassed panic.

The story has a semi-uplifting end, however. Mandel explained to Bell Canada in 2014 that a man approached him on the street to relate to what Mandel had just experienced, saying, "I just heard you on Howard Stern ... Me too."

Actress Emily Blunt is now married to actor John Krasinski, but that didn't stop Stern from prying into a past relationship when she appeared on his show in 2015. Like an awful frenemy who loves bringing up regretful stories from your past, he confronted the actress about her dating history, saying, "You haven't dated a lot of guys, you like monogamy ... and you were madly in love with Michael Bublé ... You were perfect together!"

Blunt laughed nervously and fielded Stern's questions in a very straightforward manner, refusing to say anything negative about her ex and agreeing that she loved his family. Stern then went "there," and brought up cheating rumors, saying, "[Bublé] was not faithful." Blunt exclaimed, "It's complicated ... I'm going red! ... I never want to talk about it." 

"You want me to give you closure?" Stern pressed. "Pretend right now I'm Michael, and talk to me about what went wrong, and I'll answer you as Michael." Blunt kindly refused, and the awkward moment was finally over. 

Back in December 2012, TV host Nick Cannon was still married to pop star Mariah Carey when he disclosed several decidedly not family-friendly tidbits during an interview with Howard Stern. He discussed the intimate details of his love life with Carey, answering "Absolutely!" to Stern's inquiry into if the couple ever listened to Carey's music while making love. "You know how it goes," Cannon explained. "Sometimes there's special nights when you turn the music on."

The info got even more TMI when Stern exclaimed that Cannon would pleasure himself to Carey's music. "When she's not there!" Cannon responded. Stern's co-host then asked Cannon to name his favorite Carey song, to which Cannon replied, "Hero," and explained, "I don't, like, light candles. Sometimes you've got to be reminded of what's at home ... When you hear Mariah playing, it's going down." 

Even though Cannon seemed comfortable disclosing the deets, we know we'll never watch America's Got Talent reruns the same way again.