Nick Maslow
January 08, 2018 AT 03:01 PM EST

Perhaps Oprah Winfrey’s most interesting endorsement for political office came from Donald Trump.

In 1999.

Long before he took the oath of office, the future president entertained his political aspirations on CNN’s Larry King Live. When King pushed Trump about his dream vice president, the real estate mogul immediately thought of Winfrey.

“I love Oprah,” Trump said with a smile during the interview, which CNN posted on YouTube Monday as calls for a Winfrey presidential bid gained steam following her moving speech at the Golden Globes on Sunday. “Oprah would always be my first choice.”

Trump continued singing her praises, adding: “I’ll tell ya, she’s really a great woman, though. She is a terrific woman. She’s somebody that’s very special.”

After explaining that he had “not yet even thought about it,” Trump was asked if he was kidding. “If she’d do it, she’d be fantastic,” said Trump. “She’s popular. She’s brilliant. She’s a wonderful woman. If she’d ever do it, I don’t know if she’d ever do it.”

Trump also compared himself to Winfrey, saying, “She’d be sort of like me. I mean, I have a lot of things going, she’s gotta a lot of things going.”

Jeff Vespa/WireImage; Saul Loeb/AFP/Getty Images

But Trump would not get Winfrey’s endorsement in the 2016 election. “There really is no choice, people,” Winfrey said on T.D. Jakes’ self-titled talk show less than a month before Election Day. “All the people sitting around, talking about [how] they can’t decide, here’s what I want to say.”

She went on to mention Hillary Clinton, saying, “You get in conversations — and there’s not a person in this room who hasn’t been in the same conversation — where people say, ‘I just don’t know if I like her.’ She not coming over your house!”

As the audience applauded, Winfrey continued: “You don’t have to like her. You don’t have to like her. Do you like this country? Do you like this country? You better get out there and vote.”

Should Winfrey decide to seek the White House — people in her inner circle have conflicting opinions about whether she’ll run, but CNN reports Winfrey is “actively thinking” about it — surely more focus will be put on the icon’s TV moments of yore. Near the top of the list will be Trump’s interview on Winfrey’s daytime talk show in 1988, when Winfrey asked the businessman if he wanted to run for president.

Watch both clips above.

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