Howard Stern, a renowned radio personality, gained fame and notoriety during his tenure as the host of the radio show The Howard Stern Show from 1986 to 2005.

He was known for his outspoken and controversial approach, featuring celebrity interviews, outrageous on-air moments, and fines from the Federal Communications Commission (FCC).

In 2006, Stern moved to Sirius XM and served as a judge on America's Got Talent from 2012 to 2015, displaying a more restrained persona.

Stern's celebrity interviews have often made headlines for his ability to extract personal details from stars they might prefer to keep private. The New York Times praised him as "one of the most deft and engrossing celebrity interviewers in the business."

However, not all of Stern's interviews went well, leading to uncomfortable and cringeworthy moments for the guests and the audience.

One example is when Stern had Conan O'Brien on.

Guests That Were Uncomfortable on Howard Sterns Show

Howard Stern

In 2005, Stern had Emma Bunton, aka Baby Spice of the Spice Girls, as a guest. The interview quickly turned invasive and sexist, with Stern bombarding Bunton with questions about her life and appearance. He accused her of seeking attention through her body, making her uncomfortable during the interview.

Another uncomfortable encounter occurred in 1983 when Stern had comedian Gilda Radner as a mystery guest on his show. Stern and his cohost accused Radner of ruining the show, and the interview turned awkward as they pressed her on personal matters, making her visibly nervous.

Stern's interview with Howie Mandel in 2006 caused distress for Mandel, who suffers from OCD. Stern's crew played a prank on Mandel, taking away all the tissues and forcing him to touch doorknobs, leading to an embarrassing and anxiety-inducing situation.

Related: Howard Stern Has Banned The Public From Reading His First Two Books

Actress Emily Blunt faced uncomfortable moments during her interview in 2015 when Stern probed her about her past relationship with Michael Bublé, including cheating rumors.

Conan O'Brien Kept Things Classy On The Howard Stern Show

conan-obrien

While speaking on the radio show, Stern asked O'Brien about his relationship with Lisa Kudrow. Stern brought up when she was last on his show and how she revealed she was a virgin when she got married.

So Stern then questioned O'Brien on if he had intimacy with Kudrow while the two of them were dating. O'Brien responded with, "I'm impotent."

Stern says, "Look, please, you had sex with her, right?"

Related: Here's How Much Howard Stern Pays His Staffers

O'Brien stated, "A gentleman doesn't tell tales." He also cites his religion and states he doesn't believe in premarital sex. Stern and his cohost wouldn't let up and kept questioning O'Brien, and it became clear the star was uncomfortable.

But this isn't the first time Stern has made his guests uncomfortable.

Stars Who Faced Backlash While on His Show

Howard Stern
Howard Stern in studio
via: NBC News

In 2018, Quentin Tarantino faced backlash when an old interview with Stern resurfaced, in which he defended director Roman Polanski, who had been accused of drugging and raping a 13-year-old girl. Tarantino's comments drew criticism, leading to a public apology for his insensitivity.

David Arquette's interview in 2013 also turned uncomfortable when he appeared intoxicated and made inappropriate remarks about Adolf Hitler. He later called Stern and criticized him for going to dinner with Arquette's ex-wife.

TV host Nick Cannon's interview in 2012 turned TMI when he disclosed intimate details about his love life with then-wife Mariah Carey, discussing their listening habits during intimate moments.

Stern has often sparked controversies with his provocative and shocking approach to interviews. His interviews have upset and offended celebrities like Andy Dick, Dolly Parton, Steve Allen, Carnie Wilson, and Lena Dunham, leading to public disputes and backlash.

Despite the controversies and clashes with celebrities, Stern remains unapologetic about his style and often relishes being a polarizing figure in the media. Over the years, he has built a loyal following, with many fans appreciating his candid and uncensored approach to interviews.

Related: Artie Lange Praised Howard Stern After Leaving His Show And Sparking A Vicious Decade-Long Feud

His show's ratings and popularity have shown that there is an audience for his brand of entertainment, regardless of the discomfort it may cause some guests.

While some celebrities have publicly criticized Stern for his interview tactics, others have taken a different approach. Comedian Lena Dunham, for example, turned the tables on Stern when she roasted him at his 60th birthday celebration, giving him a taste of his own medicine. This incident showcased the dynamic nature of Stern's interactions with celebrities, where he can provoke discomfort and be on the receiving end.

Stern's style and content have evolved over the years. His move to Sirius XM allowed him to push boundaries without FCC regulations. He has also demonstrated a more subdued side as an America's Got Talent judge. Still, his reputation remains intact.

Regardless of the discomfort caused during some of his interviews, he has redefined the boundaries of what is acceptable on the airwaves, and his influence can be seen in many other shock jocks and interviewers who followed in his footsteps.

As Stern continues to navigate the ever-changing landscape of media and entertainment, it remains to be seen how his legacy will be remembered in the years to come. Love or hate him, there's no denying that Howard Stern's impact on radio and celebrity interviews will be felt for generations to come.