I experienced Oprah for the first time on her 2020 live tour. This is what it was like

The longtime self-help guru brought her new live act to Brooklyn. Here’s how she wowed the crowd.

I experienced Oprah for the first time on her 2020 live tour. This is what it was like
[Photo: Paras Griffin/Getty Images for Oprah]

Oprah’s 2020 has not been off to a great start. The media mogul has been roiled by two separate controversies. Her book club’s latest pick, American Dirt, has been called stereotypical and culturally appropriative, and earlier this year she pulled her production credit from On the Record, a documentary investigating allegations of sexual assault against hip-hop mogul Russell Simmons.


These bits of bad press, though, did not stop roughly 15,000 people from packing the Barclays Center in Brooklyn for her “2020 Vision” tour launched in partnership with WW (Winfrey owns 8% of the company formerly known as Weight Watchers).

I was one of them.

Oprah has been a cultural barometer for 35 years, though having grown up abroad, I was relatively unfamiliar with Oprah: I never watched her show, which aired in daytime syndication around the country for 25 years until 2011, and hadn’t engaged much with the rest of her media empire, which extends from her magazine (O) to her TV network (OWN) to her hit podcast (SuperSoul Sundays). Just as signs of Winfrey’s zeitgeist reading appeared to be faltering with her recent controversies, she’s launched the ultimate 2020 confluence of entertainment and branding: the experiential tour.   

There’s something askance about one of the most famous non-musicians in the world developing an arena show and hitting the road. But at a time when the relentless news cycle occasionally makes me feel hopeless, and after a cancer scare—I was cleared the day before the event—I thought that a day of worship at Oprah’s semi-secular church that has inspired so many people might be just what I needed.

Oprah’s world

With tickets ranging from $30 to $200, the day attracts a diverse (though mostly female) crowd. I quickly like the women standing in line to enter the arena with me. A teacher from New Jersey tells me that this was her second Oprah event—the first one inspired her to lose 35 pounds—as we tried to ignore the phalanx of anti-vaxxers around us holding signs stating that vaccinations can cause brain encephalitis and autism and are somehow manufactured from aborted fetuses.


In Oprah’s hermetic world (attendees were not permitted to reenter if they left before it ended at 4 p.m.), nothing is crazy and everything makes sense. Nine a.m. on a Saturday is a preposterous time to host a rave, but when employees of Daybreaker, the early-morning sober dance party company flood the stage wearing sequined outfits dancing to remixes of “Ain’t No Mountain High Enough” and “I Wanna Dance with Somebody,” I immediately join in, singing along with my hands in the air. (Daybreaker proudly notes on its website that “We’re backed by science, y’all.”) At one point, a man on stage yelled “Brooklyn! Keytar!” and launched into an extended funky solo. Despite myself, I enjoy it. I am acting like a drunk uncle at a wedding—but so is everybody else.

When Winfrey walks on stage, she asks the crowd, “Is New Jersey in the house?” On its face, this is ludicrous, as if she doesn’t realize that the Nets moved to Brooklyn eight years ago, or that she really believes that that many people would trek all the way from there to here. In the dark, sealed environment of this arena, it occurs to me that I could be anywhere in the world, and if Oprah told me that we were in New Jersey, I would believe her. When a resounding roar rings out, it signals that yes, New Jersey is in the house—and Oprah always knows her audience. She jokes that instead of Oprah’s 2020 Vision Tour, they had considered calling the event the Oprah 2020 Tour, but she was worried people might get the wrong idea. Everyone laughs, but it’s also a sign that Winfrey is very aware of her power.

At the same time, she wants us to know that she is just like us: She talks about being stuck in the car on the way to work, and she professes her love for tequila (fun!) and bread (same!) multiple times. Her friends in the audience—including Lupita Nyong’o, Niecy Nash, Hoda Kotb, and Gayle King—were like mine, except rich and famous. Once in a while, though, her stories didn’t land: An anecdote about hesitating to accompany her friend Tina Turner down the red carpet at the premiere of Tina Turner: The Musical proves hard for the audience to relate to.

Oprah Winfrey congratulates members of the NYPD for their wellness transformations. [Photo: Theo Wargo/Getty Images]

Wellness Watchers

In her opening speech, Winfrey tells us that she, too, has struggled in the past, and she also found help through WW. When it was announced in 2015 that she had purchased a stake in the company and would be its public face, I thought that Winfrey was a curious choice because she has been associated with yo-yo weight loss and dieting. She addresses this during the event, playing a devastating clip where Joan Rivers made fun of her weight gain and another where she wheeled in a wagon of fat intended to represent weight she had lost on her show.

But the new WW markets itself as “beyond weight.” Realizing that its old message centered around shedding pounds was not resonating with an audience that increasingly sees talking about weight loss as body shaming, WW ditched its famous points system in favor of a model called “Beyond the Scale” and claims that “wellness” is core to its mission. At the event, Winfrey says that those who joined WW are not seeking to lose weight. Rather they are looking to find the “truest, highest expression of themselves as a human being.” This seems in contradiction to a recent WW commercial where the media mogul stated, “Inside every overweight woman is a woman she knows she can be. Many times you look in the mirror and you don’t even recognize your own self because you got lost, buried in the weight that you carry.” Her partnership with the company has been mutually beneficial until last year: The company has struggled to compete with both older (Nutrisystem) and newer (the app-based Noom) weight-loss companies.


Aside from Oprah’s opening monologue and a video highlighting NYPD officers who had lost weight through a WW program (she invited those who had lost significant amounts on stage), there is little mention of shedding pounds. But I experience some cognitive dissonance when immediately after lunch, rail-thin actress and dancer Julianne Hough, sporting a skimpy sports bra and leggings, leads us through an energetic dance routine that I (and many others) decided to sit out for fear of vomiting up the WW-branded tortilla chips that we had just consumed.

Oprah Winfrey greets audience members during Oprah’s 2020 Vision: Your Life in Focus Tour. [Photo: Theo Wargo/Getty Images]

Finding my 20/20 vision

Winfrey’s is not the first wellness event to incorporate exercise: As I considered writing this piece, a friend sent me an article about the Goop summit as a possible point of comparison. But Oprah’s endeavor is fundamentally different from Gwyneth Paltrow’s (though our morning did include a sound bowl performance and guided meditation). While happiness for Paltrow may be achieved by consuming the best combination of vitamins and wearing the right designer skirt, happiness for Oprah comes through struggle.

Her central message is that we have to work to be happy.

Chomping on an improbably delicious WW bar, I embark on my “Oprah’s 2020 Vision: Your Life in Focus” workbook “journey.” On the book’s first page, a serene photo of the porch of her home in Maui is accompanied by the quote, “This porch is a manifestation of a dream,” a sentiment reminiscent of The Secret, a book which became an international phenomenon after Winfrey promoted it. I write a contract for myself vowing to spend more time in nature by walking through Fort Greene Park, hanging out friends who make me feel good, and talking to my family more often. 

The goals are modest and achievable: Manifesting a home with a fancy porch in Maui felt like a stretch. The day before, I had been sitting in a doctor’s waiting room thinking that my goal for “2020 and beyond” was just to be alive. Oprah is the ne plus ultra of bad circumstances. She is the product of teen pregnancy, and drugs and sexual abuse are also part of her story—but her message seems to be that we are responsible for overcoming them, like she did. On another page of the book, a block quote reads, “You don’t get what you want, you get what you intend.”


It’s an appealing message that when so much is out of our hands, we can still control our happiness. But the more I think about it, the more it seems out of step with the times. Another block quote reads, “Wellness for me is simply all things in balance. We long for a life without constraint, free from conflict, fear, or judgment—where our health, relationships, career, and finances coexist in perfect flow with our spiritual center. This is the highest form of well-being.”

But what if we have no control over our health? Or our finances? As the income inequality gap widens, and companies continue to destroy the environment, it feels strange to hear her ask people to pull themselves up when it is becoming clear that the system is rigged against them.

Girl, What Are You Talking About?

Winfrey’s philosophy is also espoused by the bestselling author of Girl, Wash Your Face, Rachel Hollis, who’s a sort of Joel Osteen for the mommy blogger set, who spoke at the event. In her talk, she preached the #Girlboss gospel: “You get to decide who you want to be.” Later I flipped through her book, pausing on a page where she described the power of goal-setting and how it got her a Louis Vuitton bag she had been coveting. To Hollis, being happy is a matter of personal responsibility. 

After bounding on stage, Hollis wastes no time launching into a very (very) long story about her thinking how she had cancer in her vagina before realizing that she had in fact left a tampon in for three weeks by accident. It seems as though she was using the story to say, “We are the same! All of us have private parts and delay visiting medical professionals!” I think of alternative titles for her talk: “Girl, That’s Disgusting,” “Girl, Why Are You Telling Me This!” “Girl, I Am Begging You To Get Off Stage!”

Maybe this part was to be expected: Oprah is not known for promoting sound medical advice. The success of Dr. Phil (recently I caught an episode of his show dealing with a teenage couple that was in love but also occasionally possessed by the devil), and Dr. Oz, who has been criticized for promoting quackery, can be traced back to her show. The impact of her longstanding flirtation with junk science cannot be overstated. An appearance by actress and Playboy model Jenny McCarthy on her show popularized the anti-vaxxer movement, and perhaps even galvanized them to show up and try to convert me to their cause that morning.

Michelle Obama (left) and Oprah Winfrey (right) during Oprah’s 2020 Vision: Your Life in Focus Tour presented by WW. [Photo: Theo Wargo/Getty Images]

Preaching to the converted

The crowd’s loudest applause is saved for Winfrey’s last guest: Michelle Obama. In the 2008 election, Oprah was credited with securing the first black American president approximately 1 million votes. But on stage, the two old friends didn’t talk politics. Instead, Obama discusses having more time for Barack, loving being an empty-nester, and watching Schitt’s Creek. I ate it up. The event has felt like a hug: A day in Winfrey’s world, removed from my job, friends, family, and politics, mindlessly absorbing her and Hollis’s messages makes me feel momentarily like I could achieve anything through sheer desire and willpower.

Upon exiting the megachurch and reacclimatizing to the real world, I watch YouTube videos of Winfrey’s 2005 Legends Luncheon where she brought together 25 black women entertainers and activists. I find myself moved thinking of all the barriers that she had broken in her career, and how historic it had been for an event like that to be televised. I remember the hopeful and excited women that I had met earlier waiting in line. While flawed, Winfrey’s gospel of personal responsibility also sends a powerful message that many people can take comfort in. “You are enough.” Hit with a bad case of the Sunday scaries while writing up a to-do list for the week, I find myself scrawling one of Oprah’s mantras at the top of the page: “I can, I will, watch me.”