Each year the game show presenter hosted a festive shindig for the "Jeopardy!" team, but last year's (19) bash was a more poignant occasion due to Trebek's battle with pancreatic cancer - a fight he lost, aged 80, on Sunday, november 08.
Following the news of the TV legend's death, the "American Pie" singer paid tribute to him and revealed the show was on Trebek's "bucket list" of things to do before he died.
"Alex asked if I would come and sing for him and his Jeopardy! family at his annual Christmas party last year," McLean told People magazine. "I was on his 'bucket list,' he told me. It was at a lovely Italian restaurant near his home.
"It was a joyous and sad occasion and I was very touched that my music was that important to him. There was not the slightest hint of self-pity or weakness in this man."
Explaining how Trebek inspired him to carry himself better in old age, the 75-year-old singer-songwriter added: "He was as elegant and dignified as you saw him on television.
"Old school for sure and someone who we all can learn from. I thought of him often afterward and I'll think of him in the future and maybe try to be a little more like him."
Trebek passed away on Sunday, November 8 at the age of 80. A spokesperson for the popular quiz show tells TMZ, " 'Jeopardy!' is saddened to share that Alex Trebek passed away peacefully at home early this morning, surrounded by family and friends."