Howard Stern: A Fall from Shock Jock King to SiriusXM’s Chopping Block. A Tale of Crude Comedy, Political Preaching, and Fading Relevance
By Jack Griffin for Hussy Magazine
For decades, Howard Stern was the undisputed “King of All Media,” a title he bestowed upon himself with the swagger of a man who could say anything and get away with it. His SiriusXM show, a cultural juggernaut since 2006, is now reportedly facing cancellation as his $100 million contract nears its end in fall 2025. Sources claim SiriusXM is poised to make Stern an offer he’s unlikely to accept—a low-ball deal signaling the end of an era. But is this a negotiation tactic, a financial recalibration, or a sign that Stern’s provocative spark has fizzled into irrelevance? Once the funniest, most outrageous voice on the airwaves, Stern’s evolution from crude comedy to sanctimonious liberalism has left fans divided, critics vocal, and his legacy teetering on the edge.
In the 1990s, Howard Stern was a radio god. Broadcasting from WXRK in New York, his show reached an estimated 20 million listeners at its peak, syndicated across 60 markets. Stern’s humor was raw, unfiltered, and boundary-pushing, a middle finger to the establishment. He interviewed strippers, poked fun at the disabled, and turned “freaks” into recurring characters, all while dodging FCC fines totaling $2.5 million for indecent content between 1990 and 2004. His 1993 sketch parodying Ted Danson’s blackface performance, complete with racial slurs, is a notorious example—later defended by Stern as “crazy” shtick he owned but wouldn’t revisit.
Stern’s cruelty was part of his charm. He once called Air Florida after a deadly 1982 plane crash to ask about flights to the 14th Street Bridge, a stunt that horrified some and delighted others. His interviews were less about insight and more about shock—asking Robin Williams if he was “fucking his nanny” or grilling Donald Trump, a frequent guest, about his sexual exploits. Fans ate it up, laughing through the discomfort. “He was always a welcome distraction from the anxieties of the day,” wrote one listener in a 2022 City Journal piece, recalling how Stern’s irreverence “put life’s botherations into perspective.”
Yet, Stern’s edge came at a cost. His treatment of marginalized groups—disabled individuals, sex workers, and women in general—often crossed into mean-spirited territory. He leaned heavily on his co-host Robin Quivers, a Black woman, to deflect accusations of racism. Quivers’ presence gave him a pass, fans argued, allowing him to push racial humor that would’ve sunk others. “Howard could say what he wanted because Robin was there to laugh along,” one X user posted in 2024, reflecting a sentiment that Stern’s dynamic with Quivers shielded him from accountability.
Stern’s move to SiriusXM in 2006, with a $500 million deal, promised creative freedom from FCC censorship. Initially, he delivered, building a platform for candid celebrity interviews and uncensored comedy. But by the 2010s, the shock jock was softening. He joined America’s Got Talent as a judge from 2012 to 2015, a move that stunned fans and drew criticism from groups like the Parents Television Council for his “reputation for sleaze and misogyny.” His 2019 book, Howard Stern Comes Again, praised “evolved” celebrities like Stephen Colbert and Gwyneth Paltrow, signaling a shift toward Hollywood acceptance.
The real turning point came during the Trump era. Once a friend of Donald Trump—who appeared on Stern’s show over 20 times—Stern became one of his loudest critics. In 2024, he declared, “I don’t hate the guy. I hate the people who vote for him. I think they’re stupid. I do. I’ll be honest with you, I have no respect for you.” This wasn’t just a jab; it was a middle finger to half his audience. Stern doubled down, embracing the “woke” label in 2023: “If woke means I can’t get behind Trump, or that I support people who want to be transgender or I’m for the vaccine, dude, call me woke as you fucking want."
His COVID-19 stance was equally divisive. Stern called for mandatory vaccinations, mocked anti-vaxxers, and demanded athletes like Aaron Rodgers be fired for dodging the shot. “When are we gonna stop putting up with the idiots in this country and just say it’s mandatory to get vaccinated?” he ranted in 2021. Fans who once tuned in for laughs now heard lectures. “Howard Stern has been completely irrelevant for many years now,” posted
@CilComLFC
on X in 2024. “These comments are just a desperate ploy to gain some attention.” Another user,
@stillgray
, called him “an offended moralist and male feminist ally,” a far cry from the rebel of the ’90s.
As Stern leaned into politics, his show lost its comedic edge. The outrageous bits gave way to long, earnest interviews with A-listers like Lady Gaga, Bruce Springsteen, and Kamala Harris, who appeared in 2024 to discuss her presidential run. While Stern’s interviewing skills earned praise—conservative commentator Tim Young called him a “versatile” host despite his politics—fans lamented the loss of humor. “At one point, ‘The Howard Stern Show’ was objectively the funniest radio show of all time. That time has long passed,” an X user wrote, blaming his AGT stint for the decline.
Stern’s obsession with Hollywood acceptance didn’t help. Former staffer Steve Grillo, in his 2025 memoir Gorilla Parts, claimed Stern’s shift to “woke ideals and political correctness” was a calculated move to win over elites like Jennifer Aniston and Jimmy Kimmel, with whom he dined in 2023. Allegations surfaced that Stern ordered staff to create fake Twitter accounts in 2013 to lure celebrities, a desperate bid to stay relevant. “Every celebrity reads their Twitter,” he reportedly said, urging staff to pose as fans.
Stern’s insecurities also fueled rivalries, particularly with fellow shock jocks Opie and Anthony. In 2006, Gregg “Opie” Hughes and Anthony Cumia were fired from terrestrial radio, allegedly after Stern used his influence to silence them. Comedian Jim Norton, a regular on Opie and Anthony, later said the feud was “lucrative” for them, as the publicity boosted their profile. Hughes, now host of Opie Radio, claimed in 2024 that Stern’s desire for Hollywood approval was always an “act,” not the Long Island everyman persona he sold. “I’d be surprised if 200,000 listened to Stern on a regular basis now podcasts dominate,” Hughes said, jabbing at Stern’s fading influence. Jackie Martling, Stern’s former writer, confirmed on X in 2024 that Stern pushed for censorship of his rivals, a move that underscored his jealousy.
Now, as Stern’s contract nears its end, SiriusXM appears ready to pull the plug. Sources told The U.S. Sun that the company plans to offer Stern a deal he won’t accept, citing his high salary as unsustainable. “After you saw what happened with Stephen Colbert, it’s like they just can’t afford to keep him going,” an insider said, referencing CBS’s cancellation of Colbert’s show due to $46.2 million in losses. SiriusXM’s shift toward podcasts and younger demographics suggests a broader strategy to move away from costly legacy contracts.
Politics may also play a role. Stern’s vocal criticism of Trump and his supporters, including his 2024 claim that Trump “never wanted to be president,” has alienated conservative listeners. “If Sirius isn’t going to give Stern a good offer, I don’t think it would have anything to do with his ratings. It’s more likely everything to do with the political climate,” a source told The U.S. Sun. However, some argue his ratings have indeed slipped, with analysts noting his limited social media presence and lack of viral moments in a podcast-driven era.
Stern himself has hinted at retirement. “He is off in the summer but this year has been saying ‘maybe I should retire,’” a source told the Daily Mail. Yet, negotiations over his vast audio library suggest SiriusXM may still value his legacy, even if they won’t pay for new content. Neither Stern nor SiriusXM has commented publicly, leaving fans to speculate. “I’ve been a Howard Stern fan since the days of DC 101,” one X user posted. “But the possible retirement news today? It’s well past time.”
Howard Stern’s potential exit from SiriusXM marks the end of a five-decade reign. He redefined radio, blending crude humor with raw honesty, and built a $500 million empire. But his shift to preachy liberalism, coupled with a softer, less funny format, has left him vulnerable. The man who once mocked everyone now lectures on morality, alienating the audience that crowned him king. As one X user put it, “Howard Stern only manages to maintain a career out of legacy.”
Whether SiriusXM’s low-ball offer is a negotiation ploy or a final farewell, Stern’s story is a cautionary tale of staying true to one’s roots. He was funniest when he was fearless, crude when he was cruel, and relevant when he didn’t care who he offended. Now, as the airwaves move on, the shock jock who once ruled them faces an uncertain future—canceled not just by a network, but by a culture that no longer needs his brand of rebellion.