Howard Stern is often referred to as the “King of All Media,” and for good reason. His career has spanned decades, and over that time, he’s built a reputation for pushing boundaries, breaking taboos, and making millions laugh with his outrageous, unapologetic brand of humor. Known for his unpredictable on-air antics, Stern’s ability to shock listeners with his raw, unfiltered commentary and his fearlessness when it comes to confronting societal norms has earned him both praise and controversy. Whether it’s through interviews with celebrities, wild stunts, or biting commentary, Stern has consistently been at the forefront of radio, television, and pop culture.
Here are ten memorable moments when Howard Stern shocked the world and made us laugh:
1. The “Fartman” Entrance at the 1992 MTV Video Music Awards
One of the most iconic moments in Stern’s career was his unforgettable “Fartman” entrance at the 1992 MTV Video Music Awards. Stern, ever the provocateur, donned a skin-tight silver suit and a jetpack to make a grand entrance as “Fartman,” a character he created. The act was pure Stern—ridiculous, absurd, and absolutely shocking. But it was also hilarious, making everyone in the audience and viewers at home question just what they had just witnessed. It was the kind of stunt that only Stern could pull off, and it instantly cemented him as a force in mainstream entertainment.
2. The “Sirius XM Deal” and the $500 Million Shocker
In 2004, Howard Stern made headlines when he announced his move from terrestrial radio to satellite radio, signing a $500 million deal with Sirius XM. This wasn’t just a huge shift in Stern’s career—it was a major moment in the evolution of the radio industry itself. Stern’s decision to move to Sirius meant that his uncensored, controversial content could reach an even wider audience without the constraints of traditional radio regulations. The deal shocked the media world, but Stern’s promise to offer even more unfiltered content was a clear sign of his ability to adapt and remain at the top of his game.
3. The Interview with an “Unapologetic” O.J. Simpson
In 1994, Stern managed to secure one of the most controversial interviews in history: a sit-down with O.J. Simpson. This interview, which took place just months before Simpson was arrested for the murders of Nicole Brown Simpson and Ron Goldman, was shocking for its bluntness. Stern grilled Simpson with questions that were both uncomfortable and hilariously inappropriate, making for an interview that was as cringeworthy as it was captivating. Stern, known for his tendency to push people into uncomfortable territories, managed to get a side of Simpson that no one else had seen.
4. The “Stripper Olympics”
In the early years of his radio career, Stern was known for putting together elaborate and sometimes bizarre stunts. One of the most infamous was the “Stripper Olympics,” in which he invited strippers onto his show to compete in a series of increasingly ridiculous challenges, including pushing a shopping cart, answering trivia questions, and—of course—dancing. The segment was absurd, racy, and, as always with Stern, hilarious. It was also a perfect example of how Stern blurred the lines between shock value and comedy, creating moments that became legendary in the annals of radio history.
5. The “Lesbian Love” Game
One of the more risqué and shocking segments of Stern’s career was the “Lesbian Love” game, in which women would compete to win a prize by making out with each other. The segment, which aired on Stern’s show in the early ’90s, raised eyebrows and sparked controversy across the media landscape. It was a classic example of Stern’s ability to stir up public outrage while also tapping into a form of humor that was impossible for many to ignore. The game’s outrageousness was a deliberate move to push the limits of what was acceptable on the airwaves at the time, and Stern relished in the chaos it caused.
6. The Artie Lange Era: Artie’s Insane Moments
Howard Stern’s show entered a new phase when comedian Artie Lange became a regular member of the show’s cast in 2001. Lange, known for his dark humor and irreverent antics, quickly became a fan favorite, and his partnership with Stern produced some of the most memorable—and outrageous—moments in the show’s history. One of the most shocking and hilarious moments came when Artie openly admitted to his drug addiction on the air. While it was a serious moment, Stern’s sensitivity combined with Lange’s candidness turned the segment into something uniquely raw, real, and often darkly funny. Stern’s ability to turn vulnerability into humor in a way that didn’t trivialize serious issues was a testament to his understanding of the human condition.
7. The “Terrorist Threat” Hoax
In 2004, Stern staged one of the most famous hoaxes in radio history when he falsely reported a “terrorist threat” on his show. The stunt involved Stern’s team giving a bogus announcement that a plane had been hijacked. The entire broadcast was a detailed production, complete with fake news reports and fake phone calls, leading listeners to believe there was a genuine national security threat. Though the hoax was eventually revealed, the sheer audacity of pulling off such a prank on live radio left people questioning whether they had just been manipulated. It was the kind of stunt only Stern could pull off—surprising, audacious, and hilariously dark.
8. The “Shocking” Celebrity Interviews
Howard Stern has always been famous for his interviews, and he’s known for asking the kind of questions that others in the media wouldn’t dare ask. His unfiltered approach has led to some of the most entertaining and shocking celebrity interviews in history. One of the most memorable came in 2006 when he interviewed actor Tom Cruise, just before Cruise’s infamous public meltdown. Stern’s direct questions and humorous comments caused a few tense moments, but it was his ability to get to the heart of the story with a mix of irreverence and curiosity that made the interview both shocking and funny. Stern’s interactions with other celebrities, like Donald Trump, Madonna, and even Justin Bieber, have continually shocked and entertained audiences.
9. The “Wack Pack” and Their Wild Antics
Stern’s “Wack Pack”—a group of eccentric and often outrageous personalities who regularly appear on his show—has been a key element of his success. Some of the most memorable and laugh-out-loud moments from Stern’s career have come from the wild antics of the Wack Pack. Whether it’s the unpredictable behavior of “Beetlejuice” (the diminutive and often incoherent guest), or the antics of “Gary the Conqueror” (a self-proclaimed superhero), the Wack Pack’s unintentional humor has often left listeners in stitches. The chaos they bring to the show is as shocking as it is funny, and their antics have made them beloved staples of Stern’s broadcast.
10. Howard Stern’s “Private Parts” Movie
In 1997, Howard Stern made the leap from radio to film with the release of his autobiographical movie, Private Parts. The film was a shocking—and hilarious—insight into Stern’s life and career. With a mix of outrageous humor and raw honesty, Stern used the film to showcase the behind-the-scenes drama of his rise to fame, including the many controversies he stirred up along the way. The movie was a perfect reflection of Stern’s brand of humor—irreverent, self-deprecating, and unafraid to cross the line.
Howard Stern has spent his entire career shocking audiences, making them laugh, and challenging the limits of what can be said on the airwaves. Through his outrageous humor, controversial stunts, and candid celebrity interviews, Stern has proven time and again that he’s not afraid to push boundaries. Whether you love him or hate him, there’s no denying that Howard Stern has earned his place as one of the most influential and entertaining figures in media history.
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