Shock jock Howard Stern, 71, has built a reputation for not holding back his opinions about some of the world’s most famous and powerful people, including self-made billionaire Oprah Winfrey.
Stern called Winfrey, 71, to task on his SiriusXM radio show in 2022. In the resurfaced story, the he blasted the media maven for spotlighting her extravagant lifestyle on social media.
“Oprah’s not embarrassed by her wealth at all,” Stern expressed about Winfrey, per Business Insider.
The New York City native continued, “She loves showing it off on Instagram. It’s f—ing mind-blowing when you follow her on Instagram, you see her estates, her gardens.”
Stern then argued that Winfrey needed to be more “self-aware” about the struggles of people who have less wealth.
He also paused his criticism of the OWN founder to acknowledge her philanthropic efforts such as founding the Oprah Winfrey Leadership Academy for Girls in South Africa.
Stern added, “Her estate is unbelievable. When she goes shopping, she goes shopping in her backyard cause everything is growing back there. There’s a farm back there.”
As of March 2025, Forbes estimates Winfrey’s net worth at $3 billion. According to the business magazine, the Chicago-bred mogul partially built her fortune through ownership of the OWN network.
Stern is reportedly worth between $85 million and $650 million. In December 2020, the broadcast legend signed a five-year contract extension with SiriusXM for an undisclosed amount, although he’d previously been reported by Forbes to be making $90 million a year.
“I make a good living, and I’m having trouble watching Oprah,” Stern told his SiriusXM co-host, Robin Quivers, during his on-air rant against Winfrey.
Dish Nation covered Stern criticizing Winfrey for supposedly being too flashy with her riches. The hosts of the gossip news program, such as recording artist Tamar Braxton, sided with Oprah.
“He sounds like a hater to me. Stop hating,” Braxton said about Stern in 2022, before adding, “He got money. Just because he wanna wear jeans everyday, old tennis shoes, that’s his style and steelo.”
The “All the Way Home” singer then said, “Listen, billionaire-stylist Tamar, [would be] living the lap of luxury all over Instagram.”
Fellow Dish Nation commentator the plaintum-selling rapper Da Brat backed Braxton by saying, “It’s his ass, looking at all the stuff she got.”
Dish Nation viewers shared their opinions on what Stern had to say about Winfrey in the YouTube comment section.
One person wrote, “️If Howard don’t want to see Oprah’s wealth, then he should keep his azz off her Instagram account. It’s just that simple!”
“Does he have this same energy for Martha Stewart?” another person asked, referring to the famed lifestyle guru and television personality with an estimated $400 million net worth.
In contrast, a critic of Winfrey commented, “I’m actually on Howard’s side on this one… Oprah will do anything for money/ratings.”
Someone replied, “Oprah [is] not thirsty for money. She’s a freaking billionaire and ratings, girl, Oprah is a household name with millions of fans. She’s got millions of fans who will tune into whatever she does. She’s good.”
In addition to calling out Winfrey, Stern has also complained about members of the upper class when it comes to events like the Met Gala, the elite social affair chaired by “Vogue” editor-in-chief Anna Wintour.
In May 2024, the star of the “Private Parts” comedy biopic slammed the Met Gala, which typically includes A-list celebrity guests, according to The Things.
“It seems as though it’s a tremendous waste of time to me,” Stern is quoted saying about the annual fundraiser for the Metropolitan Museum of Art’s Costume Institute.
He also expressed, ‘Isn’t there a better charity? Like, I think what my wife is doing for animals [is better]. Give that money to that. Who f—ing cares about a museum of costumes? Wow. I mean, I don’t know anyone who has ever been to that museum.”
