Late Night Time Machine: Oprah Winfrey’s Tale of Two Tonight Show Debuts

Few can rival Johnny Carson’s status as a television icon, but Oprah Winfrey is one of them. Winfrey made her Tonight Show debut on January 29, 1985 seated across not from Johnny, but Joan Rivers, who, that year, was nearing the apex of her fame. Their first meeting would reverberate through decades.

At the time, Winfrey was ascendant. It was just a year earlier that she’d begun hosting  A.M. Chicago, a half-hour talk show airing on WLS-TV, an ABC affiliate in Chicago. It was from the same city that the king of daytime talk, Phil Donahue, was broadcasting his eponymous show. The crown would soon change hands.

“Within a few weeks, Phil Donahue was no longer top-rated,” Roger Ebert, then hosting a syndicated Chicago-based show of his own, wrote years later. “Oprah’s show was expanded to an hour and became a smash hit.” It was Ebert who advised Winfrey to ditch the ABC affiliate and go into syndication with King World. The Oprah Winfrey Show began broadcasting nationally in the fall of 1986 and the rest is history.

When Winfrey guested on The Tonight Show in 1985, it was in the relative calm before the storm—but the tides were rising.

The same was true for Rivers. By then Rivers was the bonafide second fiddle to Carson on The Tonight Show, a friend and the show’s permanent (and most popular) fill-in host. That would all soon come crashing down. Rivers, in 1986, left for Fox to host The Late Show Starring Joan Rivers. Carson never spoke to her again, and the show was canceled the following year.

However, on this night in 1985, all was well as Winfrey and Rivers began their conversation—until it wasn’t. Rivers asked Winfrey whether it was true she had won a beauty pageant. “Yeah, fifty pounds or so ago,” Winfrey responed in jest. Winfrey then explained that, in 1971, she had won the Miss Fire Prevention contest, sponsored by Nashville radio station WVOL.

Rivers, though, soon pivoted back to Winfrey’s comment: “So, how’d you gain the weight?”

“I ate a lot,” Winfrey replied without missing a beat, eliciting some quick but uncomfortable laughs from the audience.

Rivers didn’t like that answer: “No, no, no, no, no, no” she said, waving off the audience. “You  said fifty pounds. You shouldn’t let that happen to you. You’re very pretty.” Winfrey tried to interject, but Rivers continued, raising a finger: “I don’t want to hear [it]. You’re a pretty girl and you’re single. You must lose the weight.”

Winfrey then went on to insist that she would, in fact, lose the weight, explaining that A.M. Chicago would soon be hosting a “Diet with Oprah” initiative in collaboration with the Chicago Tribune. “Great,” Rivers said. “I have been put under pressure to finally do it,” Winfrey replied.

The conversation continued. Rivers said she was trying to lose five pounds, to which Winfrey replied, “you’re teenie tiny!” Rivers ignored her, instead inviting Winfrey to return in March for a check-in: “You lose 15, I’ll lose five,” she said. “Listen, I’ll lose thirty,” Winfrey replied. They then shook hands, agreeing to a return visit that never materialized.

As the years went on, Winfrey’s weight became a national obsession and tabloid fodder. On one occasion, in 1988, she entered her talk program pulling a wagon containing 67 pounds of animal fat, equivalent to the amount of weight she had lost. She later called the move one of the biggest mistakes of her life.

Nearly forty years after her appearance with Rivers, in the summer of 2024, the interview resurfaced. In an appearance on The Jamie Kern Lima Show, Winfrey brought up her Tonight Show debut as part of a larger discussion about the general obsession with her weight.

“They pre-interview you before. We’re supposed to be talking about the great success of this little talk show in Chicago that’s beating Phil Donahue,” Winfrey said, adding that Rivers “shamed” her. “And I don’t know what to do with that,” she said. Winfrey remembered the experience as Rivers saying, “Shame on you! Shame on you! Shame on you!”

Of the Rivers weight loss challenge, Winfrey said: “And I accepted. I accept that I should be shamed, because how dare me be sitting up here on The Tonight Show.”

In 1986, a year after her debut on the program, Winfrey made her first appearance on The Tonight Show with Carson behind the desk. She is visibly delighted. “I’m on The Tonight Show with Johnny Carson and Ed McMahon!” she exclaims. “I’m on too by the way,” a young voice chimes in. To her right on the couch is none other than relative unknown Jerry Seinfeld. “You’re very funny too,” Winfrey replies.

Carson and Winfrey went on to have a friendly conversation about the latter’s work, including her then-recent Academy Award nomination for The Color Purple and the success of her television program. “You have a natural ability for it, don’t you,” Carson said.

“I think what works best in television, as you know, the master of us all,” Winfrey replied, “is your ability to feel comfortable in front of the camera. And I feel real good.”

With Carson behind the desk, Winfrey got a proper Tonight Show debut.

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