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Watch: Donald Trump was obsessed with winning “Emmy Idol” in 2005

Constance Grady
Constance Grady is a senior correspondent on the Culture team for Vox, where since 2016 she has covered books, publishing, gender, celebrity analysis, and theater.

Earlier this year, it became canon that Will & Grace’s Karen is a Trump supporter. “I helped him pick out Melania!” she chirped during the show’s reunion special in September. The actress who plays Karen, however, is emphatically not. Megan Mullally dropped by The Late Show Wednesday night, and during her visit she told the story of the one time she worked with Trump.

The year was 2005, the mood American Idolcentric. It was that strange era in our nation’s history when millions of people were obsessed with watching non-famous people sing high-budget karaoke (as opposed to now, when millions of people are obsessed with watching famous people sing low-budget karaoke in cars), and so the Emmys that year were Idol-themed. Various TV stars paired up and sang covers of TV theme songs, and viewers called in to vote for their favorites.

It was, for all intents and purposes, the most low-stakes TV contest ever to occur, a joke about a funny TV trend. There wasn’t even a cash prize. But according to Mullally, then-host of The Apprentice Donald Trump had never seen a contest he didn’t immediately get obsessed with. He had to win; losing would be for losers.

So he teamed up with Mullally to sing the theme to Green Acres. He was, Mullally says, intense about taking the top prize.

You couldn’t tell it from his performance, which features Trump shambling from side to side in an arrhythmic fashion and talk-singing off-key. But Mullally, in character as Karen, threw herself and her signature comic timing into the number and carried the pair to victory.

Trump called Mullally the next day to thank her. “He said, ‘You know what, we really needed to win that thing, and we did,’” Mullally said. “‘And not only did we win it, but I hear we killed it, and it was a landslide.’”

Some things never change.

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