One ofNorm Macdonald’s most celebrated moments was when he roasted Courtney Thorne-Smith and herChairman of the Boardco-star Carrot Top, and theMelrose Placestar considers it one of the highlights of her career. The famous interview occurred on an episode ofLate Night with Conan O’Brienin 1997 when both Macdonald and Thorne-Smith had appeared as guests. Footage of the interview was uploaded to YouTube by Team Coco after Norm’s passing, and you can watch the hilarious video below.

A bulk of Norm’s barbs are focused on Thorne-Smith’s then-upcoming movieChairman of the Board. Macdonald was practically relentless with his jabs, joking that a good name for the movie would be “Box Office Poison” if Carrot Top was in it. WhenCourtney Thorne-Smithrevealed the real title of the comedy, Macdonald then asked if the “Board” inChairman of the Boardwas spelled “B-O-R-E-D.” Even though she was one of the movie’s co-stars, even Thorne-Smith could not suppress her laughter.

Looking back at the incident after Macdonald’s recent passing, Courtney Thorne-Smith, who went on topick up a recurring role on Two and a Half Men, has nothing but fond memories of that day. Speaking with Vanity Fair, she reveals how Conan O’Brien had sometimes apologized to her for the roasting in subsequent years, and she always had to remind him that it was one of the best days of her life. She also explained how she was actually grateful for Macdonald’s presence during the interview. As Thorne-Smith explains:

“Every once in a while, I’ll run into Conan and he’ll apologize, and I say, ‘That was one of my favorite moments of my life.’ Teased by Norm Macdonald? Are you kidding? … I was not thrilled about having to do [the interview], so when Norm took over, I’m like, ‘Oh, thank you, God and Norm Macdonald.’ It was a blessing. Look - had I thought thatChairman of the Boardwas my path to an Oscar, I might have been offended. I did not. So it was a joy to be teased about it. Because I didn’t know what I was going to say. I was like, ‘Good, Norm, you take over.'”

Norm Macdonald totally called it when he predicted thatChairman of the Boardwould be box office poison. It was a total dud at the box office and fared even worse with the critics. Thorne-Smith apparently also realized going in that the movie wasn’t going to get a lot of love at the Academy Awards, so she didn’t take Norm’s criticisms too personally.

For his part, Carrot Top took his roasting from thatConanappearance by Norm very well, joiningother celebrities in paying tribute online. After Macdonald’s passing, the prop comic posted a video of himself on stage specifically praising the famous bit. In the video, Carrot Top says, “Norm was a very funny dude, a unique kind of talent. I wouldn’t say we were best of friends. But I think we were friends, and I met him many times. This thing he did on Conan O’Brien is just f—ing great. So cheers to Norm Macdonald.”

On Twitter, Conan O’Brien also posted a message that read: “I am absolutely devastated about Norm Macdonald. Norm had the most unique comedic voice I have ever encountered and he was so relentlessly and uncompromisingly funny. I will never laugh that hard again. I’m so sad for all of us today.”

Many other of Macdonald’s famous pals are also in mourning.Bob Saget posted a lengthy tribute videorevealing his thoughts on losing his close friend along with some touching stories. It’s clear that everyone who knew him personally had such great respect for him, and he’ll forever be missed. This news comes to us fromVanity Fair.