Howard Stern Calls Out Oprah On Her Lavish Life

Oprah Winfrey's billion-dollar media empire was built on a key factor — her relatability. For decades, the talk show tycoon won the hearts of Middle America with a rags-to-riches backstory and a best-friend-next-door personality. Over the years, however, Winfrey has been increasingly accused of hypocrisy over her wealth and status in society. During an August 2020 installment of Apple TV+'s "The Oprah Conversation," Winfrey addressed the definition of "white privilege," opining that even socioeconomically disadvantaged Whites have more mobility on the class ladder due to their skin color, per Page Six. "Whiteness still gives you an advantage, no matter," the OWN CEO stated. With Winfrey herself boasting a current $3.5 billion net worth, many were quick to note that she owed much of her success to white females (a dominant demographic amongst her viewers). "Is she thankful for our loyalty? We white women? Nope. WE are the problem," a fan angrily tweeted. 

Winfrey's socioeconomic privilege isn't the only majorly disputed point of contention. In September 2021, actor and prominent #MeToo activist Rose McGowan labeled Winfrey a fraud for her longtime association with Harvey Weinstein. "I am glad more are seeing the ugly truth of @Oprah," McGowan wrote in a since-deleted tweet at the time (via Insider), continuing, "She is about supporting a sick power structure for personal gain, she is as fake as they come."

Now, another public figure has taken aim at the Harpo CEO, once again dragging her wealth into the forefront of the conversation.

Howard Stern thinks that when it comes to money, Oprah Winfrey should practice a little more humility. On a November 28 episode of "The Howard Stern Show," the ever-opinionated shock jock said of Winfrey's wealth, per Entrepreneur, "It's f***ing mind-blowing when you follow her on Instagram. 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." In particular, Stern mused in wonderment over Winfrey's backyard farm and the "people who serve her." Stern acknowledged his own impressive $650 million net worth, stating, "I make a good living, and I'm having trouble watching Oprah."

According to the Daily Mail, Winfrey became a millionaire by 1989 and a billionaire by 2000, the latter making her the first Black woman to do so. Her current main property is her Montecito, Calif. estate, which sprawls 66 acres and boasts a 23,000-square-foot mansion.

Stern, however, did praise his fellow member of the media for her philanthropic work with The Oprah Winfrey Leadership Academy for Girls, a school for locals in South Africa. "Every Thanksgiving she welcomes the African gals at her boarding school in Africa ... She provides, she gives them an education. She gives them meals," Stern conceded, admitting that Winfrey's achievements with the school are "impressive."