10 Of The Most Controversial Moments That Happened In ‘The Howard Stern Show’
via Nicki Swift / YouTube
Few radio shows have stirred up public reaction quite like The Howard Stern Show. From its early days in the ’80s to its heyday in the ’90s and beyond, the program has made headlines for all the wrong—and sometimes intentional—reasons. Whether it was breaking taboos, ridiculing celebrities, or using shock as a strategy, Howard Stern knew how to get people talking.
While some moments were dismissed as boundary-pushing humor, others sparked real outrage. Stern’s tendency to mix satire with personal attacks often left his targets reeling and audiences divided. From tasteless stunts to aggressive interviews, the show didn’t just toe the line—it bulldozed right past it.
Even as Stern attempts to soften his public image in recent years, the echoes of his most explosive broadcasts continue to resurface. The following list dives into ten of the show’s most controversial moments—instances that defined both his career and his reputation as one of radio’s most polarizing figures.
1. He Let a Caller Use the N-Word Repeatedly During a Paris Hilton Tape Interview
In 2004, Howard Stern invited professional poker player Rick Salomon onto his show to talk about the now-infamous sex tape he made with Paris Hilton. While the conversation was already controversial by nature, things escalated when a caller phoned in and repeatedly used the N-word live on air. Stern didn’t intervene, which led to public outrage and consequences from several media outlets.
The backlash was swift. Multiple stations dropped The Howard Stern Show, and the Federal Communications Commission (FCC) issued hefty fines. Stern pushed back, accusing the FCC of waging a “McCarthy-type witch hunt” against him. The controversy, while damaging in some respects, also pushed Stern to consider a long-term exit from traditional radio.
He ultimately made the jump to satellite radio, joining Sirius XM, which was still in its early stages. CBS Radio wasn’t thrilled with Stern using his final shows to promote his new platform. In response, CBS filed a $9 million lawsuit against him, further cementing this moment as one of the most contentious turning points in his career.
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2. He Made a Lewd Joke About Aunt Jemima and Received a $600,000 Fine
In 1992, Howard Stern sparked outrage when he made a racially charged joke involving Aunt Jemima, the advertising mascot for a line of pancake mixes and syrups. His comment was crude and explicit, describing a sexual act involving the character’s image. It was one of the earliest examples of Stern crossing a line that even his most loyal fans found hard to defend.
At the time, conversations around racial stereotypes in branding weren’t as prominent as they are today, but even then, the comment was deemed offensive. The FCC didn’t hesitate to take action, slapping Stern with a $600,000 fine for the broadcast. This marked one of the first major times that regulators flexed their power against his show.
The moment is often cited when discussing the many ways Stern tested societal boundaries for the sake of shock value. While some labeled it dark humor, others saw it as blatantly racist and unnecessary. The controversy still lingers in conversations about his earlier radio days.
3. He Spliced Dolly Parton’s Audiobook to Make Her Sound Racist and Inappropriate
In 2008, Stern targeted country music legend Dolly Parton by airing doctored audio clips from her audiobook My Life And Other Unfinished Business. The spliced segments made it sound like Parton made racist remarks and joked inappropriately about children. For fans of Parton and many listeners alike, the segment was nothing short of appalling.
When confronted about the segment, Stern brushed it off as satire, saying it was “obviously parody” and “funny as hell.” But not everyone saw it that way. The manipulation of Parton’s voice and message struck a nerve, especially since she had no involvement in the skit or any way to defend herself in real-time.
Dolly Parton later expressed her shock and hurt, stating she had never felt so humiliated. Though she chose not to pursue legal action, the public reaction was loud and largely negative. This incident remains one of the most glaring examples of how Stern’s brand of humor could cross deeply personal and ethical lines.
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4. He Pressed Robin Williams on a Rumored Affair and Later Regretted It Deeply
Howard Stern’s 1990s interview with Robin Williams is remembered not for its humor or insight, but for how uncomfortable and invasive it became. At the time, rumors swirled that Williams had an affair with his children’s nanny, who would later become his second wife. Stern zeroed in on the gossip, repeatedly badgering the actor with questions about his personal life.
Stern later admitted he regretted the entire approach. In a 2017 interview, he called the moment one of the biggest mistakes of his career. He recalled playing to the crowd rather than respecting Williams as a guest, pushing crude jokes instead of fostering a meaningful conversation. For Stern, it was a lesson in how not to conduct an interview.
Williams never publicly addressed the interview in detail, and Stern said he never had the chance to apologize before the actor’s tragic death in 2014. The incident is a haunting reminder of how Stern’s confrontational style could sometimes do lasting harm, even to people he admired.
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5. He Made Lewd Comments to Emma Bunton About Her Body and Virginity
In 2005, Howard Stern hosted former Spice Girl Emma Bunton on his show and used the opportunity to bombard her with a series of deeply inappropriate questions. He asked when she first started menstruating, when she lost her virginity, and when her breasts developed—questions that clearly made the pop star uncomfortable.
Bunton kept her composure and declined to answer, but Stern doubled down with more crude remarks. He commented on her body, fantasized about her in explicit scenarios, and even dismissed her father’s hypothetical disapproval by saying, “He loves it.” The tone of the interview was aggressive, objectifying, and widely criticized after airing.
Even as Bunton tried to laugh it off, her discomfort was obvious. Stern’s refusal to respect boundaries in that interview is often brought up when discussing the show’s most inappropriate moments. It remains one of the more glaring examples of his disregard for personal and professional lines.
6. He Interviewed Dana Plato the Day Before She Died of an Overdose
In May 1999, Diff’rent Strokes star Dana Plato appeared on The Howard Stern Show in what would become her final public interview. During the broadcast, Plato insisted she was sober, despite years of public battles with drug addiction. When skeptical callers accused her of being under the influence, she offered a lock of her hair to Stern’s team for drug testing in a defiant attempt to prove them wrong.
According to Stern, Plato changed her mind right after the show ended and asked for her hair back, leading him to believe she hadn’t been truthful. Less than 24 hours later, she was found dead of an overdose involving a lethal combination of Valium and painkillers. The interview was widely replayed, and the eerie timing led to speculation about whether the appearance contributed to her death.
Stern, however, denied any responsibility. He claimed that Plato thanked him after the show and seemed to be in good spirits. “Maybe we gave her her last good time,” he later reflected. Despite his dismissal of the criticism, the timing of the interview added a tragic and controversial footnote to both Plato’s legacy and Stern’s.
7. He Asked Why the Columbine Shooters Didn’t Rape Their Victims
In one of his most widely condemned moments, Howard Stern made horrifying remarks the day after the Columbine High School massacre in 1999. On-air, he questioned why the shooters didn’t have sex with the “good-looking girls” before killing them and taking their own lives. The comments drew immediate national backlash.
Stern’s exact quote was, “If I was going to kill some people, I’d take them out with sex.” The timing and subject matter were especially shocking given the fresh grief and trauma surrounding the tragedy. Community leaders, media outlets, and parents all called for accountability, and Denver’s Rocky Mountain News publicly stated that Stern had no place on local airwaves.
Politicians in Colorado also condemned the broadcast, demanding an apology that never came. Major advertisers, including Geico, Priceline, and Mitsubishi, dropped their sponsorships. The moment marked one of Stern’s lowest points with the public, and while he never apologized directly, it served as a wake-up call for just how far his shock tactics could go.
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8. He Mocked Selena’s Death With Gunshot Sounds Over Her Music
In 1995, just days after the murder of beloved Tejano singer Selena, Howard Stern aired a segment that mocked her death. He played her songs overlaid with gunshot sound effects and followed up with derogatory remarks about Latino music and culture. The comments immediately ignited widespread outrage.
Stern dismissed Selena’s music as lacking soul and even claimed that “Alvin and the Chipmunks have more depth.” He didn’t stop there—he went on to mock the emotional reactions of her fans, accusing them of overreacting. The comments were seen as racially charged and deeply insensitive given the context of Selena’s violent death.
Latino communities across the country responded with protests and boycott threats. KEGL-FM in Dallas, which aired Stern’s show, quickly released a statement distancing themselves from the remarks. The backlash forced a rare level of public scrutiny onto Stern, with many demanding an apology that, once again, never came.
9. He Took John Bobbitt’s Side and Called Lorena Bobbitt a ‘Psycho B*tch’
After Lorena Bobbitt severed her husband John’s penis in 1993—a response to years of reported abuse and rape—Howard Stern wasted no time turning the story into spectacle. Stern publicly supported John, paid for his cosmetic surgery, and invited him to appear on the show multiple times. Meanwhile, he mocked Lorena’s appearance and questioned her claims of abuse.
Stern’s narrative minimized the gravity of domestic violence and turned a traumatic incident into entertainment. He later made on-air remarks like “No creep deserves what that psycho b*tch did,” doubling down on his support for John Bobbitt. His interviews were frequently crass and dismissive of the abuse allegations.
Years later, Lorena Bobbitt reflected on how the media, especially Stern, missed the opportunity to foster a meaningful conversation around domestic abuse. She emphasized that she had never received an apology from him. The episode remains one of the more uncomfortable examples of how The Howard Stern Show often sacrificed humanity for ratings.
10. He Made a Joke About a Plane Crash That Killed 78 People
Back in 1982, when Howard Stern was still a D.C. radio personality, he made one of his earliest controversial jokes following a real-life tragedy. Just after Air Florida Flight 90 crashed into the Fourteenth Street Bridge in Washington, D.C., killing 78 people, Stern made a mock phone call to the airline on air. “What’s the price of a one-way ticket to the Fourteenth Street Bridge?” he asked. “Is that going to be a regular stop?”
The call was played as a bit, but it left a bitter taste for many listeners who felt it was wildly inappropriate so soon after a major disaster. The segment attracted attention beyond D.C. and marked the beginning of Stern’s reputation as a so-called “shock jock.” For his fans, it was a sign of his fearless comedy; for critics, it was proof of his cruelty.
Years later, Stern reflected on the moment in an interview with David Letterman. He said he was full of rage and broadcasted with “pure id,” using the platform to unleash unfiltered emotion. While he acknowledged it wasn’t healthy or balanced, he stopped short of expressing regret. That moment, though early in his career, helped set the tone for the controversies that would follow.
