Old Howard Stern Interviews With Trump Resurface, Reigniting Scrutiny of His Past Remarks

NEW YORK — A series of decades-old radio interviews between Donald J. Trump and Howard Stern have resurfaced during the 2025 campaign cycle, prompting renewed scrutiny of the former president’s past remarks about women, sexuality, and power — comments that once drew limited attention but are now being reexamined in a markedly different political climate.

The recordings, aired on The Howard Stern Show between the late 1990s and mid-2000s, feature Mr. Trump speaking candidly — and at times crudely — about women, relationships, and his personal life. While the interviews were widely known among Stern’s audience at the time, they have taken on new significance as they circulate online amid broader debates over character, credibility, and fitness for office.

The renewed attention comes as Mr. Trump faces multiple legal challenges and mounting political pressure, with critics arguing that the recordings offer insight into longstanding patterns of behavior rather than isolated lapses.

“No Filter” Radio, Reconsidered

Mr. Trump appeared on The Howard Stern Show more than 20 times over nearly two decades, establishing a rapport with Mr. Stern that was built on provocation, humor, and shock value. At the time, Stern praised Trump as one of his most entertaining guests, describing him as unusually willing to speak without restraint.

In later interviews, Mr. Stern has said that the context mattered — the show thrived on exaggeration and transgression — but he has also acknowledged that many remarks now appear more troubling when removed from that environment.

“One of the things that made him compelling was that there was no filter,” Stern said in a post-2024 interview. “But there’s also something revealing about what someone says when there’s no filter.”

Among the most widely circulated clips are discussions in which Mr. Trump comments on women’s appearances, makes sexually explicit jokes, and speaks about dating much younger women. In one interview from the early 2000s, he joked that sexually transmitted diseases were his “personal Vietnam,” a line he later said was intended humorously and not as a comparison to military service.

At the time, the remark generated little backlash. Today, it is frequently cited by critics as emblematic of a dismissive attitude toward both public health and veterans.

Comments About Ivanka Trump Draw Renewed Criticism

Several of the most controversial excerpts involve Mr. Trump speaking about his daughter, Ivanka Trump, during on-air exchanges with Mr. Stern. In a 2004 interview, Stern made a sexually explicit comment about Ms. Trump’s appearance, which Mr. Trump did not directly rebuke. In a later 2006 appearance, Mr. Trump discussed his daughter’s looks and body while she was present in the studio.

These moments, which circulated widely online in mid-2025, prompted renewed criticism from advocacy groups and political opponents, who described the remarks as inappropriate and disturbing.

Supporters of Mr. Trump have argued that the comments were made in a shock-radio setting and should not be treated as serious political statements. But cultural critics note that norms have shifted substantially since the early 2000s.

“What was once dismissed as crude humor is now understood as part of a broader conversation about power, objectification, and consent,” said a professor of media studies at New York University.

The Epstein Files and a Changed Context

The timing of the clips’ resurgence is significant. In July 2025, renewed attention to documents and testimony related to Jeffrey Epstein — the disgraced financier who died in custody in 2019 — reignited national debate about elite networks, accountability, and sexual exploitation.

Although Mr. Trump has not been accused of criminal wrongdoing in connection with Epstein, critics argue that his past rhetoric on women and sexuality has taken on new weight in light of that broader reckoning.

One 2006 Stern interview, in which Stern and co-host Robin Quivers jokingly referred to Mr. Trump as a “sexual predator,” has circulated widely. In the clip, Mr. Trump appears to smile and respond affirmatively in a moment that critics say now appears jarring, even if intended humorously at the time.

Snopes and other fact-checking organizations have confirmed that the clip is authentic and unedited.

Stern’s Break With Trump

Mr. Stern, who once described Mr. Trump as a friend and attended his 2008 wedding, has since become one of his most vocal media critics. Stern endorsed Hillary Clinton in 2016, Joe Biden in 2020, and Vice President Kamala Harris in 2024.

In recent broadcasts, Stern has said that he believes Mr. Trump has not fundamentally changed since their radio conversations years earlier.

“I think he’s the same person,” Stern said. “What changed is the stakes.”

Stern has also rejected claims that the interviews were unfairly weaponized, arguing that they accurately reflect Mr. Trump’s own words.

Political Impact and Public Reaction

The resurfaced interviews have fueled protests and demonstrations in several cities, particularly among younger voters and women’s rights advocates. While it is unclear whether the clips will materially shift voter behavior, strategists from both parties say they contribute to an already polarized narrative.

“Very few voters are undecided about Donald Trump at this point,” said a Republican strategist. “But these clips reinforce impressions — for supporters and critics alike.”

Mr. Trump’s campaign has largely dismissed the renewed attention, describing it as a distraction driven by political opponents and media hostility. Campaign aides have emphasized economic messaging and immigration policy, while declining to engage substantively with the content of the recordings.

A Cultural Reckoning, Years Later

The Stern interviews underscore how media artifacts can acquire new meaning over time. What once passed as edgy entertainment is now being reassessed through the lens of evolving social norms and heightened expectations for public officials.

For Mr. Trump, the recordings serve as a reminder that his pre-political persona — cultivated in tabloids, reality television, and shock radio — remains inseparable from his political identity.

Whether the renewed scrutiny alters the trajectory of the campaign remains uncertain. But as the clips continue to circulate, they are shaping the broader conversation about power, accountability, and the long shadow of words spoken into a microphone years before the consequences were fully understood.