"American Pie" singer Don McLean opens up about being invited to perform at Alex Trebek's annual Christmas Party

Turns out, Alex Trebek is a huge fan of “American Pie” singer Don McLean. And that feeling is now mutual.

“It’s funny, because I felt like I’d always known the guy,” McLean, 74, tells PEOPLE, of being invited to play several of Trebek’s favorite songs at the Jeopardy! host’s annual Christmas party for his friends and staffers, which was held at Feinstein’s at Vitello’s in Los Angeles on Dec. 20. “But as far a [playing] the party goes, it was something that just came out of the clear blue sky,” McLean says.

Trebek told the crowd at the party that he personally reached out to McLean’s team through his website inviting him to perform, and McLean jumped at the chance. Once at the venue, he says he was handed a list of Trebek’s favorite songs to play, including “Castles in the Air,” “Crying,” “Wonderful Baby,” “Vincent,” and yes, “American Pie.”

“I don’t take direction well, and I’ll get up and walk out of something if I don’t like it,” McLean says with a laugh. “I’ve never had a boss. But he was such a nice person, and I realized this was so important to him. When I told this story to the audience… that he had basically scripted my set, they were laughing because they know him. They know how he is. But I said, ‘I’m going to do exactly what he tells me!’ They were roaring.”

Alex Trebek, Don McLean
Credit: Jeremy Westby/2911 Media

McLean says the party was a great success, and that Trebek, 79, was happily mingling with everyone. “He was right there, kidding around. He was upstairs, downstairs, all over the restaurant.”

McLean adds, “He’s a very funny guy. A very joyful person. A happy person. This is a sh—y thing to be in the middle of,” he says, referring to Trebek’s current pancreatic cancer battle, which he was diagnosed with last March. “But he didn’t wear it on his sleeve. He was just easygoing and funny.”

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Alex Trebek, Don McLean
Credit: Jeremy Westby/2911 Media

Still, he says emotions were running high at the event.

“There were a lot of tears,” McLean says. “The songs can do that But under the circumstances, there was also a propensity to want to let some emotion out. Everyone is trying to be joyful, but there is this undercurrent of worry.”

As far as Trebek’s joy at having McLean perform? He told the crowd, “I can officially take this off my bucket list. This was a real treat for me.”

Trebek is hosting Jeopardy!: The Greatest of All Time tournament, which kicks off Jan. 7 at 8 p.m. ET on ABC.