Oprah Confessed That She Has Very Few Friendships, Then Shared The Names Of Her Inner Circle

Oprah is massively successful by any metric. She’s rich beyond most people’s wildest dreams, for a start. At the turn of the millennium, she officially became a billionaire. And she’s remained near the top of the so-called richest celebrities’ lists ever since. Analysts think that she pulls in at least $300 million per year. Not bad going!

The money isn’t necessarily everything for her, though. Oprah is a big philanthropist — philanthropy of course being a great help when it comes to making friends. She divides a lot of her cash between foundations, including her own, and global charities such as the Clinton Foundation and Free the Children.

Unsurprisingly, Oprah also has shelves full of awards. Yup, she’s bagged a whopping 18 Daytime Emmys, two Primetime Emmys, and she’s also gained two Academy Award nominations for her work in the movies. And thanks no doubt to the aforementioned philanthropy, in 2013 she received the highest award an American civilian can get, the Presidential Medal of Freedom.

Oprah’s wealth has given her the ability to purchase pretty much whatever piece of real estate she likes. She reportedly has at least $200 million in land — not to mention some pretty impressive houses. She’s got property in Maui, Colorado, and Montecito, and her main residence is apparently a massive $90 million mansion.

But who gets to visit these magnificent houses and hang out with Oprah? Well, a surprisingly small number of people it transpires. Speaking on the podcast Making Space with Hoda Kotb in October 2021, Oprah dropped a sudden revelation. She told the host, “I don’t have a lot of friends.”

That’s not to say she doesn’t have good relationships with other celebs, of course. One particularly interesting one is her friendship with Tyler Perry. In December 2010 Oprah wrote in her O magazine, “It doesn’t surprise me that Tyler Perry and I have become close friends in recent years. There’s a similarity in our paths: Each of us has been on a journey that can only be called a miracle.”

The two of them definitely have similar backgrounds. Both experienced poverty and abuse before making it in the world of show business, and they bonded over this. Oprah wrote in her magazine article, “When I’m near him, I have the same experience I had back when I first went to one of his stage productions: I leave feeling more connected to others, like I just came from church.”

But perhaps even more interesting is Oprah’s relationship with her long-term partner, Stedman Graham. They’ve been together for an impressive 35 years at this point, but never actually married. Looking at their life together sheds light on how Oprah approaches relationships in general.

Oprah wrote about Graham in a 2020 article for O magazine. Upon first meeting him, she said, she assumed he was a “player.” Then, she “proceeded with caution, even with a friendship. It wasn’t until months later, when I learned he’d broken up with his girlfriend and had been inquiring about my dating status, that I gave him a serious thought.”

Graham proposed to Oprah in 1992 — but the wedding never went ahead. Oprah said in her O article many years after the fact, “I wanted to know he felt I was worthy of being his missus, but I didn’t want the sacrifices, the compromises, the day-in-day-out commitment required to make a marriage work. My life with the show was my priority, and we both knew it.”

But it wasn’t just about putting the career first. Oprah, it seems, simply isn’t a fan of marriage as an institution. In 2017 she told Vogue magazine that if she and Graham had ever tied the knot “We would not have stayed together, because marriage requires a different way of being in this world.”

Oprah went on, “His interpretation of what it means to be a husband and what it would mean for me to be a wife would have been pretty traditional, and I would not have been able to fit into that.” And when asked “What has not getting married taught you about women in our society?” she answered, “Live life on your own terms.”

It’s clear that Oprah very much does live life on her own terms, and there are only a handful of people she truly shares that life with. When she listed her friends to Hoda Kotb after stating that she didn’t have many, the list consisted of only three people. Tyler Perry wasn’t on there, and perhaps Stedman Graham is in a different category altogether.

Oprah revealed the names of her only close friends to the Making Space podcast: Gayle King, Maria Shriver, and Bob Greene. Two of those names you might recognize as Oprah’s fellow celebrities. Oprah remembered during the interview that, “Gayle and Maria, I met around the same time” and she’d known them both for 42 years. Who’s Bob Greene, though?

Bob Greene is a fitness expert, and one Oprah credits with changing her life. In 2007 she wrote an article about him and his work for O magazine, saying, “I feel like I’ve always known Bob Greene, though the truth is it’s only been 14 years since we first met. My life has not been the same since.”

Greene helped change Oprah’s attitude to her health, you see. She wrote in the article, “When I first met Bob and he asked me why I was overweight, I thought he was being a smart-ass. I was overweight for the same reason everybody else is, I answered smugly. I loved food. It took me a while to get to the truth. I didn’t love food. I used food to numb my negative feelings.”

Oprah remembered, “In 1992 I won another Emmy for best talk show host. I had prayed that Phil Donahue would win so that I wouldn’t have to embarrass myself by rolling my fat butt out of my seat and walking down the aisle to the stage…. I had filled journals with prayers to God to help me conquer my weight demon.”

Bob Greene, Oprah wrote, “was the answer to my prayers.” She said, “When I first met Bob at that last-ditch-effort spa in Colorado, I thought for sure he was judging and labeling me as I had already judged and labeled myself — fat and out of control. Bob, it turned out, wasn’t judging me at all. He really understood.” And that sparked a lifelong friendship that continues to this day.

Oprah has a different but no less strong relationship with Gayle King. She’s another friend Oprah has written extensively about in O magazine. In 2006 she noted, “We’ve been close since she was 21 and I was 22, and have been through a lot together: my previous bad relationships, her divorce.”

That same month the pair debunked a rumor that had often swirled around them. Asked in a joint interview for O magazine whether they were romantically together, Oprah answered, “I understand why people think we’re gay. There isn’t a definition in our culture for this kind of bond between women. So I get why people have to label it – how can you be this close without it being sexual?” 

But it really wasn’t sexual. King said, “The truth is, if we were gay, we would so tell you, because there’s nothing wrong with being gay.” And Oprah added, “I’ve told nearly everything there is to tell. All my stuff is out there. People think I’d be so ashamed of being gay that I wouldn’t admit it? Oh, please.”

Years later in 2018 Oprah sang the praises of King when she was inducted into the Broadcasting & Cable Hall of Fame. Oprah declared of her friend, “She deserves to be celebrated, not just for her news acumen, but for being her consistently joyful, vibrant, best-outlook-on-life, best-outlook-on-everybody self.”

And in 2020 Oprah interviewed King herself for the first time. During Oprah’s Vision Tour she sat down with her friend, and they discussed their almost lifelong friendship. King said, “The secret to me is trust. I trust you totally, even if I disagree with you, I still trust you… we’re honest with each other and trust each other and actually are very like-minded.”

That just leaves Oprah’s other close friend Maria Shriver. Shriver was present at Oprah’s side when she did the Making Space with Hoda Kotb podcast, and both of them revealed some fascinating tidbits about their relationship and how it started. Oprah believed they had always shared a “spiritual connection.”

Oprah remembered that she first met Shriver while both of them were working at WJZ-TV. She said, “[She] was in the bathroom, literally, splashing water on her face, and we started a conversation. I forever think that that was, like, a divine moment that happened because she was one of my true, grounded friendships that carried me through my entire career.”

As for Shriver, she remembered that Oprah used to bring her cups of coffee at work, and that cemented their friendship. She said, “In a funny way, even though I had a very close relationship with my mother, I wasn’t nurtured, mothered in that way, right? And [Oprah] wasn’t mothered in her own way. But I think, in a way, we have mothered each other.”

You might recognize the name Maria Shriver for a reason unconnected to Oprah, and that’s because she used to be married to the famous actor Arnold Schwarzenegger. Their relationship very publically fell apart in 2011 when news hit that Schwarzenegger had previously fathered a love child with the family’s maid, Mildred Baena.

Oprah was there to support Shriver as she went through the painful divorce. The day after Schwarzenegger confessed to the affair, Shriver appeared on Oprah’s last ever show as a special guest, looking stunning. And in the hours before the show started, she was seen in a restaurant with both Oprah and Gayle King.

During the show Shriver told Oprah, “For more than 30 years, you bestowed the most amazing friendship on me, given me love, support, wisdom and most of all truth. I know I would not have gone on without receiving those gifts from you. You believed in others so they could believe in themselves.”

It’s clear that Oprah’s most important friendships are strong and life-affirming. But is there room for anyone else in her life? During the Hoda Kotb interview, Oprah mentioned that “recently” she had “expanded that circle” and “had become friends with a couple of people in my later adult life in the past five years.”

Oprah didn’t name these people, so who could they be? One possibility is Prince Harry and Meghan Markle. She was one of the guests at their wedding in 2018, for a start. And after the ceremony was over she told the Entertainment Tonight show she thought the event was a “cultural moment.”

Oprah has repeatedly stood up for the couple whenever they’re slammed in the media. In a 2019 This Morning conversation with King, she said, “I feel that if people really knew [Meghan] they would know that she is not only everything you perceive her as being — graceful and dynamic in holding that position — but that she just has a wonderful warm, giving, funny heart.”

The chat show queen also sent the couple’s baby son Archie some books as a present when he came into the world. She told the Access Hollywood show in 2019, “I have a standard gift that I do for people that I really care about. I don’t know the baby’s name or the baby’s gender, but this baby will have enough books to last a lifetime.”

That same year, Oprah told Entertainment Tonight that Meghan had made the right decision to go against royal protocol to keep her baby’s birth private. She said on the show, “To be able to stand up and say this is what I really want for my baby and my family and now I’m going to do it a different way when it's been done that way for a thousand years? I’m just so proud of her.”

And of course it was Oprah who sat down with Prince Harry and Meghan for their bombshell interview in 2021. After it took place, Oprah told journalist Nancy O’Dell “Our shared intention was the truth. They wanted to be able to tell their story and tell it in such a way that allowed them to be as truthful as possible.”

Is Oprah also close to Meghan’s mother, Doria Ragland? We don’t know the full details, but the two women seem to be forming a friendship. Reportedly Ragland, who is close in age to Oprah, spent a whole day at the TV star’s house at some point before the wedding. 

A few people suggested that Oprah was angling to get an interview with Ragland, but she soon set them straight. She told Entertainment Tonight, “The story was that Meghan’s mom had come to my house and she left laden with gifts. You know what the gifts were? First of all, she’s great at yoga, so I said, ‘Bring your yoga mat and your sneaks in case we just want to do yoga on the lawn.’”

Ragland did leave the house with lots of fruit, however, fruit from Oprah’s own tree. Oprah explained, “It was a basket of kumquats, people. For all of the people who said I am getting her gifts and I’m trying to bribe her for an interview — they were kumquats. If kumquats can get you an interview, I’m all for it!”

So there are some contenders for who Oprah’s new friends might be, but she seems to be perfectly content no matter how many people are in her inner circle. And that’s probably a good thing — especially when you consider that there are quite a few celebrities who aren’t big fans of the star...

“It was like being at someone’s house who doesn’t really want you there.” That’s how Ludacris described his 2005 appearance on The Oprah Winfrey Show to promote Best Picture Oscar winner Crash. The hip-hop star made that shocking revelation in a 2006 interview with GQ magazine, saying that he’d been unfairly targeted after Winfrey had called him out for his questionable lyrics about women.

Ludacris also claimed that Winfrey was anything but the perfect host off air. In the same GQ interview, the Dirty South rapper alleged that many of his comebacks had been cut out of the broadcast. He added, “Of course, it’s her show, but we were doing a show on racial discrimination, and she gave me a hard time as a rapper when I came on there as an actor.”

Winfrey has unarguably become just as renowned for her humanitarian and philanthropic work as her talk show career. And in the 2000s, she added to her list of many achievements when she opened up a South African boarding school designed to help girls from deprived areas to fulfill their potential. But when Winfrey asked for help from a celebrity to promote the academy, the star in question declined the invitation.

You see, while Angelina Jolie is no stranger to humanitarianism herself, she reportedly felt as though she couldn’t play a part in Winfrey’s project. The Oscar winner was allegedly upset with the way that the talk show host had appeared to take Jennifer Aniston’s side in the tabloid-baiting love triangle involving Brad Pitt.

“Kiss from a Rose” singer Seal isn’t particularly renowned for courting controversy. In 2018, though, he made headlines by insinuating that Winfrey had been aware of the Harvey Weinstein scandal long before it became public. The vocalist took to Instagram to post a meme that read, “When you have been part of the problem for decades, but suddenly they all think you’re the solution.”

Seal also used several photos to back up his point – one of which sees Winfrey planting a kiss on the disgraced producer. He accompanied the meme with the message, “Oh I forgot, that’s right… You’d heard the rumors, but you had no idea [Weinstein] was actually serially assaulting young starry-eyed actresses who in turn had no idea what they were getting into. My bad.” Ouch.

Mo’Nique’s feud with Winfrey looks to date all the way back to 2010. In the same year that she won the Oscar for her performance in hard-hitting drama Precious, the actress and comedienne agreed to let Winfrey interview her older brother. And during the conversation, Gerald Imes admitted to sexually abusing Mo’Nique as a youngster, backing up his sister’s previous allegations.

Yet while Mo’Nique may have been consulted about the interview beforehand, she claims that she wasn’t made aware her mother and father would be sitting in the audience, too. The star believes, moreover, that her parents had never grasped the severity of the situation and that Winfrey had betrayed her trust by inviting them onto the set. For her part, the host apparently told the comedienne that she didn’t know her folks would be present. Mo’Nique has also suggested that Winfrey may have had a hand in her having seemingly been snubbed by Hollywood since her Academy Awards victory.

Winfrey and Whoopi Goldberg have thankfully managed to patch up their differences in recent times. However, for roughly three decades, the pair barely spoke. The drama began when Goldberg picked up a Best Actress Oscar nod for her performance in The Color Purple – a moment that biographer Kitty Kelley claims upset co-star Winfrey.

Interestingly, Goldberg never appeared as a guest on Winfrey’s show following the film’s release, while she was also notably absent from the talk show host’s Legends Ball in 2006. But the two ultimately made amends when they bumped into each other at a Tyler Perry party and learned that their apparent beef was all simply a misunderstanding.

50 Cent incurred the wrath of the talk show queen in 2006 when he described her as an “Oreo” during a chat with Elle magazine. The rapper argued, too, that while Winfrey had “started out with black women’s views, [she] has been catering to middle-aged white American women for so long that she’s become one herself.” And to add insult to injury, 50 also named a pet dog after the TV host.

However, the two appeared to make up when 50 guested on Oprah’s Next Chapter in 2012. The rapper explained that he’d been upset by Winfrey’s snubbing of hip-hop, revealing, “I would see moments when you would discuss your feelings on the [rap] culture. And everything that was wrong with the culture was what was on my CD, and I was like, ‘Oh, she doesn’t like me.’”

It seems that Winfrey probably shouldn’t expect any Christmas cards from Randy Jackson. And that’s despite the fact that the host invited his mom, Katherine, and father, Joe, onto her show in 2010 in the wake of his brother Michael’s death. However, the King of Pop’s sibling was allegedly left seething by the interview – owing, it appears, to Winfrey’s actions five years beforehand.

You see, in 2005 Winfrey addressed the subject of pedophilia on several episodes of her hit show. This, of course, just happened to be during the same period when Michael was on trial for child molestation. And Randy believes that Winfrey deliberately scheduled these episodes for that time as a ploy to help put Michael behind bars.

What’s more, Winfrey apparently added Janet to the list of Jackson family members that she’s riled when she interviewed Michael’s three children in 2010. Allegedly, the “Rhythm Nation” singer was left angry after hearing about the televised chat and subsequently accused Winfrey of exploiting Prince, Paris and Blanket in a quest for ratings. In fact, she reportedly even tried to stop the interview from going ahead.

And according to the National Enquirer, Janet and Winfrey were at loggerheads shortly before the chat took place. The tabloid reported, “The two women had a blistering blow-up during a telephone call on the day that the show was taped. When Oprah made it clear that she was going ahead with the interview, Janet screamed, ‘Oprah, you make me sick!’”

Another daytime talk show stalwart is said to have started an all-out war with Winfrey in 2007. In that year, gossip site TMZ reported that celebrity chef Rachael Ray had made all sorts of derogatory comments about the star during a drunken night out. Perhaps the most damning, however, was the claim that Winfrey had been in “slave drag” while appearing in the 1998 film Beloved.

Yes, the seemingly mild-mannered Ray reportedly argued that Winfrey had an issue with “being black” as she continued to get more “loud and aggressive.” The star also allegedly described Winfrey as a “demanding b***h,” according to the National Enquirer. Nevertheless, Ray’s camp was quick to deny that such inflammatory insults had ever been uttered.

In the wake of Chris Brown’s attack on then-girlfriend Rihanna in 2009, Winfrey hosted an episode of her show that tackled the issue of domestic violence. And following the transmission, the R&B singer told People magazine that he felt as though he’d been thrown under the bus. He said, “I did a lot of stuff for [Winfrey], like going to Africa and performing for her school. She could have been more helpful, like, ‘Okay, I’m going to help both of these people out.’”

A Winfrey representative responded to Brown, however, through a statement that read, “Oprah is very appreciative that Chris Brown performed at her school, but she takes domestic abuse very seriously. She hopes he gets the counseling he needs.” That didn’t placate Brown, who told radio station Hot 97, “As a young black man myself, I need older black male role models to step in and kind of mold me. Not people-bashing me, ’cause that’s not how you learn from mistakes.”

Winfrey’s relationship with Jonathan Franzen has been turbulent, to say the least. In 2001 the author kicked things off by describing the host’s famous book club as “schmaltzy” and “one-dimensional” while in conversation with Salon. Franzen even took umbrage with Winfrey’s decision to select one of his own novels, The Corrections, telling the website, “I see this as my book, my creation, and I didn’t want that logo of corporate ownership over it.”

But Franzen later changed his tune and even accepted an offer to appear on Winfrey’s show. He said to The New York Times, “I said things that ended up hurting [Winfrey’s] feelings… I feel bad because the person being hurt is actually a really good person for American writing and reading.”

Roseanne Barr is certainly no stranger to the celebrity feud, and in 2008 she added Winfrey to her list of targets. In particular, the motormouthed comedienne criticized the TV legend for favoring Barack Obama over Hillary Clinton in the Democratic presidential primaries. And on her official website, Barr described Winfrey as a “closeted Republican” who didn’t like “other women who actually stand for something to working American women besides glamour, angels, Hollywood and dieting.”

However, less than 24 hours later, Barr said sorry for her harsh words towards Winfrey. She wrote, “I got upset because I felt Oprah was adding to the divisiveness in this country. I am sorry, Oprah, I really do admire and love you for all the good you do and have done in this country and the world at large.”

“She’s had damn rapists, child molesters and lying authors on her show. And if I’m not a rags-to-riches story for her, who is?” It seems fair to say that Ice Cube isn’t particularly happy about seemingly being constantly snubbed by the Queen of All Media. Yes, the rapper has never been asked to be a part of Winfrey’s show, and in 2006 he told FHM that he believes she has a “problem with hip-hop.”

Ice Cube also referred to the specific occasion when his co-stars Eve and Cedric the Entertainer were both invited to promote the movie Barbershop on the show – but he wasn’t. Yet Eve’s appearance perhaps undermines his argument that Winfrey hates hip-hop. And the media mogul herself even later told MTV, “I’m not opposed to rap. I’m opposed to being marginalized as a woman.”

The late great Joan Rivers was never one to hold back, and she certainly lived up to her cutting reputation when she interviewed Winfrey on The Tonight Show in 1985. In her cookbook, Food Health and Happiness, Winfrey recalled the incident – which just so happened to take place during her national TV debut – writing, “I was starting to settle in. And then it happened. Joan interrupted with perhaps the only question I hadn’t prepared for: ‘So, how’d you gain the weight?’”

“[Rivers] wagged her flawlessly manicured finger at me, pointed out that I was still ‘a single girl’ and challenged me to come back 15 pounds lighter next time she hosted,” Winfrey continued. And Rivers didn’t go any easier on the star over the years, either. Indeed, an insider reportedly once told the National Enquirer that the comedienne believed Winfrey was “the biggest phony in the world.”

In 1995 David Letterman publicly made Winfrey an enemy with a jibe at her expense while hosting the Oscars. He didn’t help matters, either, when he introduced a sarcastic segment on his late-night hit called Oprah Log. Yet Letterman claims that his beef with Winfrey actually began long before the Academy Awards incident.

In 2010, you see, Letterman told The Daily Show’s Jon Stewart that he had first encountered Winfrey when he was having lunch on vacation with his girlfriend. The star admitted that as a joke he had told the waiter, “Oh, this woman right over there [Winfrey] has been kind enough to take care of our check. We got a free lunch, and that’s where it started.” Finally, though, the pair patched up their differences in 2005.

James Frey no doubt rues the day that he ever agreed to appear on The Oprah Winfrey Show. By then, the writer had already topped The New York Times’ Best Sellers list with his 2005 semi-fictionalized memoir A Million Little Pieces – largely thanks to Winfrey’s seal of approval. However, after Frey graced the show, website The Smoking Gun decided to research his story, with the investigation ultimately discovering that much of the information presented in the book as fact had been entirely fabricated.

Then, when Frey returned to the show at the start of 2006 to explain his actions, Winfrey said that he’d “betrayed millions of readers.” The TV icon embarrassed the author’s publisher, Nan Talese, to boot when she also appeared on set to justify the book being marketed as an autobiography. Talese would later criticize Winfrey for her “fiercely bad manners.”

In 2009 Winfrey met pop provocateuse M.I.A. at a Time magazine party honoring some of the 21st century’s most influential people. Yet it seems that their encounter didn’t exactly go swimmingly. Recalling the incident in a 2015 interview with Rolling Stone, M.I.A. said that she had asked Winfrey to help shine the spotlight on the oppressive regime of her native Sri Lanka. However, it’s claimed that the TV icon had little interest in talking to someone who had previously been so “rude to Lady Gaga.”

M.I.A. alleged, “[Winfrey] shut me down. She took that photo of me, but she was just like, ‘I can’t talk to you because you’re crazy and you’re a terrorist.’ And I’m like, ‘I’m not. I’m a Tamil, and there are people dying in my country. And you have to, like, look at it because you’re f**king Oprah, and every American told me you’re going to save the world.’”

Iyanla Vanzant apparently clashed with Winfrey in 1998 following a misunderstanding about a new talk show. After appearing on the host’s series to promote her book In The Meantime, the inspirational speaker subsequently became a protégée of the TV legend. But unfamiliar with how the industry worked, Vanzant ended up cutting her ties with Winfrey when she approached the other woman to help her launch her own vehicle.

Vanzant told syndicated U.S. radio show The Breakfast Club, “I was just being naive and stupid and asking, but it wasn’t received well. And that created a breakdown in communication. But we were able to repair that. It took 11 years… They didn’t think I was ready [for my own show], but that was never communicated to me.”

Toni Braxton certainly didn’t appreciate Winfrey’s opinion when she went bankrupt for the first – but not the last – time. In particular, the R&B singer was chastised by Winfrey for possessing Gucci cookware in her kitchen at a time of serious financial trouble. And Braxton hit back as a result, calling the TV star “so frickin’ mean” in a 2012 episode of Behind The Music.

In fact, Braxton even went on to claim that Winfrey had made a damaging impact on her career. Several years later, however, the chart-topping singer appeared to let bygones be bygones. In any case, Braxton agreed to portray unsung hero Darlene Love in a TV movie biopic screened on Winfrey’s OWN network.

Winfrey doesn’t appear to be a particularly gracious loser, according to Anjelica Huston. In an interview with New York magazine, the actress revealed that Winfrey had reportedly snubbed her ever since the pair had gone head to head in the same Oscars category in 1986. On that occasion, Huston ended up winning the Best Supporting Actress gong for her turn in Prizzi’s Honor – and apparently Winfrey has never forgiven her for it, either.

Huston added, “The only encounter I’ve had with Oprah was when I was at a party for the Academy Awards [at] a private residence. I was talking to Clint Eastwood, and [Winfrey] literally came between us with her back to me. So all of the sudden I was confronted with the back of Oprah’s head. Nobody else would dislike me so much as to literally, physically come in between the person I was talking with that way.”