Howard Stern Says He’s Not Beefing With Oprah, But She’s Probably Afraid of Him

The battle of the talk-show titans would have been a lot more exciting if it were more than a one-sided cold war — and if it were 1995. 

For decades now, Howard Stern, the king of shock jock radio and the antithesis to Oprah Winfrey’s family and housewife friendly media empire, has been taking the occasional pot shot at the queen of daytime TV, criticizing her ostentatious use of wealth and her deceptively skeevy content practices. Perhaps Stern is jealous of Oprah’s more widespread acceptance by buttoned-up American society. Maybe Oprah wishes she could fire back, but her squeaky-clean public persona prevents her from joining Stern in the mud. Whatever the motivations behind the action or inaction in the near-feud, the friction between Stern and Oprah has yet to escalate into a full-on fight.

Stern recently spoke to Watch What Happens host Andy Cohen on SiriusXM, where Cohen asked Stern about what seems to be some long-standing acrimony between him and Oprah, but Stern denied that any sort of feud has been brewing. “I love Oprah,” Stern dubiously claimed, though he doubts the feeling is mutual.

“I think about who are Howard Stern’s kind of enemies at this point, or punching bags, and I get the sense that you’ve either publicly or privately kind of mended fences with them," Cohen told Stern during their conversation. “But it seems like Oprah might be the only kind of Howard Stern foe or enemy that you still have.”

“No, I love Oprah,” Stern swiftly denied the accusation, saying, “I follow Oprah. I enjoy watching Oprah.”

Perhaps Cohen brought up Oprah because, as far back as 2004, Stern has been publicly wondering why the media giant never seems to receive the kind of criticism that he does. When Stern was under fire from the Federal Communications Commission over the racy, obscene and scatological humor that typified his lauded radio sensation The Howard Stern Show, the host pointed fingers at Oprah for platforming conversations about teenage sexuality on daytime TV, declaring, “If they fine me, they gotta fine Oprah — the darling of the world.” 

Soon after, the FCC launched an investigation into The Oprah Winfrey Show.

But in recent years, Stern’s ax to grind with Oprah has been centered around her public displays of extravagant wealth, such as when he attacked Oprah’s social media presence in 2022. “It’s fucking mind blowing when you follow her on Instagram,” Stern said on his show. “You see her estates, her gardens, the people who service her and, you know… She’s got servants and, like, people cooking and it’s fucking wild. She knows how to be rich.”

Stern added, “She kind of likes to show it off, which is something I’m not comfortable with. I don’t think that people should show off their wealth.”

Nevertheless, in his recent conversation with Cohen, Stern insisted that he and Oprah have no bad blood, nor have they ever met in person, which Stern attributes to his intimidating presence. “I think she’s afraid,” Stern said of a possible meeting of the minds. “I know Gayle King very well. And I think at one point she suggested, ‘Oh, we should get together with Oprah.’ I said, ‘You better check with Oprah. You better. Don’t surprise her with me.’”

Furthermore, Stern said he is “fascinated by Oprah,” specifically by her opulent Instagram page. “I like sometimes how Oprah is so unaware,” Stern said. “Maybe she is aware, but I suspect, I’m an Oprah follower, but sometimes she’s unaware of the sort of way she shows her wealth. I couldn’t do that.”

“I’m not saying that she’s wrong. We all know she’s wealthy,” Stern said of Oprah’s conspicuous consumption. “But I think in the world right now, there is such a disparity between those who have and those who have not. And it’s only getting worse. So I find it funny. And I’m not gonna sit there and tell you I don’t think it’s funny. I go, ‘Wow, Oprah is unapologetically wealthy,’ and good for her.”

“But I don’t hate Oprah at all. I think she’s brilliant,” Stern closed, though he didn’t specify exactly what makes Oprah so dazzling, in his opinion — but you'll probably get a better answer from her jeweler.