The longtime Jeopardy! host held his annual Christmas party at Feinstein’s at Vitello’s in Los Angeles on Wednesday, when he expressed to his friends, staff and colleagues that they were in for a real treat: a surprise performance by Don McLean, as seen in PEOPLE’s exclusive photos from the night.
As it turns out, Trebek, 79, had long dreamt of having the American singer/songwriter perform for him and even tried to bring his music to the Jeopardy! stage before finding out that it was out of budget.
Fast forward to this year, when Trebek began researching whether the “American Pie” crooner was still performing while planning his party — and ‘lo and behold, he was.
“I sent an email to Don’s people on his website and here we are tonight,” Trebek told the audience at the party. “I can officially take this off of my bucket list. This was a real treat for me.”
The party was entirely planned and executed by Trebek personally, and the TV host even hand-picked the seven songs McLean performed for the crowd.
“I had never met Alex and normally I just come in and do my thing,” said McLean, 74. “When I arrived, Alex handed me a piece of paper with a list of songs he wanted me to perform and in the order he wanted them performed in. Then when I looked next to each song, he had timed them out.”
“I looked at Alex and said, ‘Well, tonight is your night and I will do exactly what you want,’ ” he continued. “And that is what I did. Except I did toss in one Christmas song in the spirit of the event! Alex is a wonderful man and is loved by the world.”
In addition to McLean, comedian Paula Poundstone also surprised the crowd with a performance.
It’s been a challenging year for Trebek, who announced his diagnosis with stage 4 pancreatic cancer in March.
During his cancer battle, the star has often expressed how much he’s appreciated the ongoing outpouring of love and well wishes from fans around the world. In May, he told PEOPLE that he had been responding extremely well to his first round of chemotherapy.
“I’ve got a couple million people out there who have expressed their good thoughts, their positive energy directed towards me and their prayers,” he said. “I told the doctors, this has to be more than just the chemo, and they agree it could very well be an important part of this.”
In September, he announced that he was once again undergoing chemotherapy.
“I was doing so well and my numbers went down to the equivalent of a normal human being who does not have pancreatic cancer, so we were all very optimistic,” he said on Good Morning America. “They said, ‘Good, we’re going to stop chemo, we’ll start you on immunotherapy,’ and I lost about 12 lbs. in a week and my numbers went sky-high, much higher than they were when I was first diagnosed.”
While he told GMA at the time that he hoped to continue hosting Jeopardy! for as long as he could, he said in October that there may be a point in the not-too-distant future when he has to step away from the beloved game show.
“I will keep doing it as long as my skills do not diminish, and they have started to diminish,” he told Canada’s CTV News. “I’m sure there are observant members of the television audience that notice also, but they’re forgiving. But there will come a point when [fans and producers] will no longer be able to say, ‘It’s okay.’ “