In 1985, Joan Rivers asked Oprah a question. Three years later, she wheeled out a wagon of fat.

"What size are you, by the way?"

It's the pointed question, asked by Oprah Winfrey on her self-titled talk show, that's dated particularly badly over the last two decades. 

Oprah was speaking to 17-year-old actors Mary-Kate and Ashley Olsen in 2004, during an interview watched by millions in America alone. At the time, Mary-Kate was being relentlessly photographed and covered in the press because it was suspected she had an eating disorder. Watching the clip back now, the tension is palpable. 

"I know there's been a rumour that has recently surfaced that's really upset you..." Oprah says to Mary-Kate.

"You know," she continues, "the one about the eating."

Mary-Kate's twin sister Ashley replies, "Yeah, you know, people are going to write what they're going to write. We try not to read the good or the bad because it just kind of comes with the territory. Either you're too fat or you're too skinny."

Oprah then interrupts Ashley to ask, "What size are you by the way?" 

"Size…?" Ashley clarifies, then adds, "I'm short!" 

Mary-Kate interjects to say the sisters have always been petite, and Oprah interrupts again. 

"Oh, you're not sure? That's so interesting," she says, and the audience starts laughing. 

"I'm obsessed with size and you're like, 'I really don't know!'"

Later that same year, Mary-Kate Olsen checked into a rehabilitation facility to seek treatment for a food-related health disorder.

It's now far more widely understood that eating disorders are complex and severe, with anorexia being one of the deadliest mental health conditions. By today's standards, Oprah's interview with the Olsens is deeply misguided, especially given they were still teenagers. 

Mary-Kate (r) and Ashley Olsen (l) in 2004. Image: Getty. 

But for those of us who grew up watching The Oprah Winfrey Show, it's also entirely unsurprising.

Oprah had and continues to have a long and very public relationship with her own weight, often tackling it as a subject on The Oprah Winfrey Show and in her highly circulated magazine, O!

In 1988, Oprah famously wheeled a red wagon onto the stage of her national television show. Wearing a slim pair of Calvin Klein jeans, a tight, black top, and a black and gold belt around her waist, she pulled 67 pounds of animal fat behind her - the exact amount of weight she'd lost in four months by replacing her meals with shakes. 

"If you can believe in yourself, and believe that this is the most important thing in your life... you can conquer it," she told her studio audience. 

At the time, 62 million - or one in four - Americans were watching. It would go down as the highest rating episode of Oprah's 25-year run. 

Of course, Oprah had "literally starved" herself for four months, and two days after eating normally, those Calvin Klein jeans no longer fit. 

Three years later, she appeared on the cover of People and vowed to never diet again, before going on to co-write a book a few years later, titled Make the Connection: Ten Steps to a Better Body and a Better Life. 

By 2002, she announced she'd made peace with her body, but a few years later she was asking, 'how did I let this happen again?' This being weight gain. 

Oprah has since gone on to describe the 'wagon of fat' as a "big, big, big, big, big, big, big mistake."

"When I look at that show, I think it was one of the biggest ego trips of my life," she told Entertainment Tonight in 2011.

"The ego was my belief that being in those Calvin Klein jeans made me worthy as a human being, or more valuable, or made me better," she said.

Listen to Cancelled on Oprah Winfrey. Post continues after audio.

The wagon of fat has gone down in pop culture history as an example of our pathological obsession with weight loss - an obsession that has far more to do with aesthetics than health. Over the years, Oprah routinely came back to those conversations around body weight, shape and size, but the wagon of fat seems like the insidious start of it all. A moment of stigmatising fat, and telling an audience of - primarily women - that if they just cared enough, theirs could be set aside too, rather than attached to their bodies.

Justifiably, Oprah's dialogue around weight is now being interrogated, with people questioning how the most influential woman in the world may have impacted the body image of a generation of viewers. When Oprah suggested a diet, people tried it. When she got the advice of a health professional (even when their claims were widely debunked), people listened. When she said things like, "All the success doesn't mean anything if you can't fit into your clothes. It means the fat won," people believed her. 

It would be a simple story if we could point the finger at Oprah, holding her accountable for the culture that disrupted countless women's relationships with food and their bodies. If we could label her an aberration, with a calculated awareness of how women's self-loathing would make certain companies a lot of money. 

But, of course, that's not the full story. It's more complicated than that. 

In 1985, a 31-year-old Oprah Winfrey sat opposite comedian Joan Rivers during her first ever appearance on The Tonight Show. 

At this point, Oprah had been working in media for almost a decade, but primarily in radio. In the last year, she'd been hosting AM Chicago, a morning TV show that was faltering when she took over. Now, her show was the highest rating program on the network, and months after this interview, it would be renamed The Oprah Winfrey Show.

In the footage from that appearance, Oprah wears a navy dress with signature 80s shoulder pads and statement earrings. She doesn't hold herself with the same confidence she does now - she was younger and less experienced, but still unmistakably warm. Initially, Rivers asks Oprah about her success in beauty pageants as a teenager. Then, suddenly, she changes direction.

"So how did you gain the weight?" Rivers asks. 

Oprah glances at the floor. She pauses, then smiles.  

"I ate a lot," she says. 

"You shouldn't let that happen to you!" Rivers shouts. "You're very pretty."

When Oprah starts to speak, Rivers interrupts. "I don't want to hear!" she says. "You're a pretty girl and you're single, you must lose the weight."

Oprah then brings up the singer Nell Carter, who had recently been on the show, and had herself lost weight. "Oh yes, but you couldn't tell," Rivers says. "She's still very chubby, she needs to lose more."

Rivers goes on to say, "you must tell a friend the truth! You must say you're still a pig, lose more weight. That's a friend."

Oprah Winfrey and Joan Rivers in 1985. Image: NBC.

More than 30 years later, Oprah wrote about this exchange in her cookbook, Food, Health and Happiness.

She recalls, "It was all going smoothly; 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?’

"Wait a minute - did she just use my national television debut to ask me why I was so fat? The studio started spinning. The word fat… fat… faaaaatttttt reverberated in my brain."

Oprah goes on to describe how the "audience laughed nervously" as Rivers "wagged her flawlessly manicured finger at me."

"And the whole time I just sat there smiling breezily," she writes, "wanting nothing more than to crawl under my chair."

From the moment she appeared on television, Oprah was placed in a world that said - in no uncertain terms - that a woman's worth was tied to her weight. It's what we're missing when we cringe about the wagon of fat, or gasp about Oprah's interrogative questioning of a teenage girl with an eating disorder. She too was a casualty of diet culture. 

It's uncomfortable when a person is a victim of the very harm they've gone on to perpetuate, but it's far more common than we like to believe. 

Almost 40 years on from the day Oprah wheeled a wagon onto her stage, and almost 20 years from her insensitive interview with Mary-Kate and Ashley Olsen, we can acknowledge that elements of The Oprah Winfrey Show dated badly. But what we forget when we try to judge the past by the standards of the present is context. An understanding of the messy, challenging reality that the people who define an era are also the product of it, and have their own experiences that inform their values and beliefs. 

It's unclear whether Oprah's views on weight have evolved. Just this year, she shared a video of herself throwing out a cake to 'reset' her diet for 2022. But perhaps we should look at the painful moments of her show less as evidence that she is bad, and more as evidence that we have changed. We're more sensitive and considered in how we discuss eating disorders and weight, and hopefully that also means we understand how Oprah's views were internalised from the damaging messages around her. 

A 30 second clip from an old interview rarely tells the whole story, and often the context - as tedious as it might feel - is far more interesting. 

For more from Clare Stephens you can follow her on Instagram and TikTok.