The kids had nothing to do. It was the cocktail hour before a dinner party in Massachusetts, and B.J. Novak, years away from playing Ryan Howard on “The Office,” was a boy standing around with his family, waiting.
They’d been told one thing ahead of time, and it was the reason he was paying attention.
“I was 12 years old. It was 1991,” Novak told David Letterman, in a clip the official Letterman channel posted on September 13, 2025. “And we were told that a man my father was working with was invited to a dinner at Deepak Chopra’s house in Western Massachusetts. And we were told that Michael Jackson was going to be at the dinner.”
Novak’s father is the author William Novak, and the family is from Newton, outside Boston. Chopra, the writer and doctor, was a friend of Michael’s for about 20 years. The house, as Novak remembers it, was in Lincoln, Massachusetts. “I’m in eighth grade,” he said.
Then the guest of honor arrived, and he didn’t stroll in. “A man just runs in in a red military uniform and a black top hat and mirrored sunglasses and sits behind a book on the Beatles,” Novak said. The boy couldn’t believe the real one had just come through the door. “And I thought, well, this has to be a Michael Jackson impersonator.”
B.J. Novak tells David Letterman about his dinner with Michael Jackson
The whole clip is this one story, and it runs 2 minutes and 50 seconds. Novak gets to the dinner table at about 0:52 and to the game at about 1:50.
“We sat down at dinner and I was seated next to him,” Novak said. “There was no conversation for like two minutes straight. Everyone was just too shy.”
So a full table sat there, and nobody could find a first word. Michael found it himself, and he gave it to the kid beside him.
“And then finally he says to me, ‘So, do you like music?'”
Novak said yeah. Michael didn’t introduce himself or explain who he was. “And I couldn’t make this up,” Novak told Letterman. “He pulls out of his coat pocket three CDs. They are Aerosmith album ‘Pump,’ the Beatles album ‘Let It Be’ and the Kris Kross album.”
Novak had a simple explanation for it. “He had just gone to Tower Records,” he said. Michael had been to the record store like any other music fan, and he still had his new CDs on him at dinner.
That wasn’t the end of the evening. “And then we played Categories,” Novak said.
Categories is the parlor game where a letter gets picked and every player has to come up with a word starting with it for each category on the list. Michael’s letter was N, and Novak still remembers one of his answers. “I was very impressed,” he said, because Michael “got a double word score under fictional characters for Nicholas Nickleby.” Novak drew his own conclusion for Letterman: “So he’s a Dickens reader.”
Michael won the game. Novak saved the celebration for the end of his story.
“Then when he won, he sang two a cappella bars of ‘We Are the Champions,'” Novak said. “Absolutely gorgeous.”
Two bars of Queen’s victory song, with no band behind him, for a dinner table and a 12-year-old he’d just beaten at a word game. It also settled the question the boy had been carrying since the cocktail hour. “So there’s no doubt now that it’s Michael Jackson,” Novak said.
He finished the story with the morning after. “Who would have believed me the next day at school?” he said. “I had dinner last night with Michael Jackson and we played Categories and he won.”