Oprah's Most Glaringly Out-Of-Touch Moments

Talk show legend Oprah Winfrey has faced countless accusations of being completely out of touch over the years. While she is known for giving out generous surprise gifts to her show's audience, she is equally known to spend lavishly on herself. Her spoiled lifestyle is no secret, as Oprah has openly provided countless examples of how she does not live like the rest of us. From multiple private jets to not even answering her own phone, her life is entirely unrelatable to the average person. Oprah's net worth makes the talk show host even richer than you realize, which places her at an eye-popping $3.5 billion.

Oprah has gained massive and well-earned success through her hit talk show series, "The Oprah Winfrey Show" that aired for over three whole decades from 1986-2011. Her groundbreaking work as an actress, host, producer, author, and philanthropist launched her into stardom. She later became the face of WeightWatchers, for whom she has served as a brand ambassador and significant shareholder in the company. While her namesake show ended in 2011, Oprah has never left the public eye, remaining a frequent topic of conversation that is still making headlines for both good and bad reasons. 

While promoting her movie "The Color Purple" in December 2023, Oprah Winfrey made purple cocktails to celebrate the film. In an Instagram video, Oprah just stood and watched as Lera Franklin did all the work to mix a custom purple drink and walk viewers through a step-by-step tutorial of how to make it themselves at home. "@thecolorpurple has taken over my life so much that now we're making Purple drinks at my house. Recipe in the video by @lerafranklin that you can make cocktails or mocktails—and just in time for the movie," Oprah captioned the post. The special drink recipe included apple juice, beet juice, lime juice, ginger, blue Curaçao, simple syrup, sparkling water, and topped off with a blackberry garnish.

While having someone making themed drinks in your home is already an unrelatable experience for the average viewer, the drinks were not the most out of touch aspect of the video. The video was filmed inside her $50 million home in Montecito, California. The white cabinets and fine China offer only a small glimpse into how nice and sleek the interior of her home is. She purchased the massive mansion in 2001, highlighting just how rich and luxurious her life has been for decades. 

On Facebook, many flocked to the comment section to discuss the set up inside her mansion. "This is a great idea. Have a chef in your mansion," one Facebook user commented on the video, which received laughing reactions. Another user laughed at the out-of-touch scenario portrayed in the video. "I love how this bartender is just in some random kitchen in Oprah's basement making drinks love it. Wish I was there," they commented. 

It is no secret that Oprah Winfrey has tied a lot of her personal brand to weight loss. She has been the face of WeightWatchers for decades as one of their top ambassadors, after all. In 2015, she further attached her legacy to the weight loss program by buying 10% of the company. She has admitted that she had been on a constant weight loss journey for the majority of her life, revealing her struggles to maintain her ideal weight while always being in the spotlight. While many people can relate to dieting and trying to lose weight through various means, the average person does not center their life and brand around weight loss quite like Oprah. 

Oprah swears by the effectiveness of WeightWatchers, claiming that it does not negatively impact or restrict her lifestyle or eating habits. "WeightWatchers is easier than any other program I've ever been on. It's a lifestyle, a way of eating, and a way of living that's so freeing. You never feel like you are on a diet, and it works," she said (via Page Six). "I can honestly tell you I struggle no more. I'm eating everything I love — tacos, pasta. I've never felt deprived."

Given Oprah's weight loss transformation, she decided to publicly denounced Ozempic as it rips its way through Hollywood. "When I first started hearing about the weight loss drugs, at the same time, I was going through knee surgery, and I felt, 'I've got to do this on my own,'" she said during a panel called "Oprah Daily's The Life You Want: The State of Weight" (via People). "Because if I take the drug, that's the easy way out." Meanwhile, most people will likely never find themselves on Ozempic or WeightWatchers. 

For nearly three entire decades, Oprah Winfrey has had the unique privilege of never having to step foot in a bank. Even though "The Oprah Winfrey Show" took off in 1986, she was able to stop going to the bank entirely by 1988. During a YouTube segment for "The Ellen Show" in 2017, Oprah revealed to Ellen DeGeneres that after 29 years of avoiding banks, she had finally gone to the bank herself just for fun. 

"What did you go to the bank for?" DeGeneres asked Oprah in the video. "To deposit a million dollars," Oprah responded. "Yeah, I just wanted to go there just to do it. I stood in line, just to do it. It felt fantastic. Actually, it was $2 million," Oprah joked right before the segment concluded. They both laughed, undoubtedly realizing how unrelatable the scenario was to viewers. This was not the first or last time celebrities and the ultra-rich have found joy in performing common chores that usually frustrate regular people. Since they have the privilege of not being forced to do these tedious tasks in their everyday lives, the extra work and inconvenience become a novel experience. While Oprah claimed she enjoyed running this common errand, she admitted she does not even have a pin number.

During an interview with the cast of "A Wrinkle in Time," Oprah also revealed she does not pump her own gas. "I wouldn't know what to do," she joked to E! News TV host Sibley Scoles. While her co-stars laughed at her confession, the comment was painfully out of touch to viewers.

For many years, Oprah Winfrey has garnered criticism for her frequent use of a private jet. She is not the only celebrity to face backlash for this environmentally harmful practice, including Taylor Swift. The private jet she owned for almost a decade cost a staggering $75 million, and that did not include the jet fuel, maintenance, and crew each time she decided to use it. The Gulfstream G650 private jet was built in 2015 and could fit 14 to 18 passengers. She now owns a bigger Gulfstream G700 that was built in 2024 and previously owned a 2013 G550.

How Oprah spends her billions especially attracted attention when she took her private jet all the way to Australia. In December 2025, she flew on her private jet to Sydney for her Australian speaking tour. Social media users pointed out the excess carbon emissions from Oprah's private jet, calling her hypocritical for her talks about saving and protecting the planet. 

During Oprah's "A Wrinkle in Time" cast interview where she admitted she does not pump her own gas, she also mentioned how she does not know how flying commercial even works any more since she no longer does it. "I actually took someone to the airport recently and I said: 'Make sure you have your ticket,' and they were like: 'What?' And I said: 'They don't have tickets anymore?'" Oprah told E! News. Just to add to her growing reputation of being out of touch, she made sure to add that she does not even answer her own phone. "I actually have security," she told Jimmy Kimmel on his show while promoting the same film. "Somebody does answer the phone and they'll say, 'Mr. Kimmel is on line two.'"