Norm Macdonald’s death has left fans around the world shocked and saddened.

“In every important way, in the world of stand-up, Norm was the best. An opinion shared by me and all peers,” tweeted David Letterman. “Always up to something, never certain, until his matter-of-fact delivery leveled you. I was always delighted by his bizarre mind and earnest gaze. (I’m trying to avoid using the phrase, 'twinkle in his eyes'). He was a lifetime Cy Young winner in comedy. Gone, but impossible to forget.”

Conan O’Brien expressed similar sentiment. “I am absolutely devastated about Norm Macdonald,” the former late night host admitted. “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.”

These reactions would be expected -- both O’Brien and Letterman had close relationships with Macdonald, the late comedian having been a regular guest on their respective programs. But to see the truth breadth of Macdonald’s influence and legacy, one should look to the people who were regularly the butt of his jokes.

Frank Stallone, one of Macdonald’s favorite non sequitur punchlines during his stint on Saturday Night Live, admitted he was “saddened” to learn of the comedian’s death. “He had a lot of fun with me on weekend update with, ‘You Guessed It Frank Stallone.’ I thought it was funny,” Stallone wrote on Instagram. “My only regret was that I never got to do the show with him. I thought he was an original and very funny.”

Likewise, senator Bob Dole, who Macdonald impersonated on many occasions, tweeted his condolences. “Norm Macdonald was a great talent, and I loved laughing with him on SNL. *Bob Dole* will miss Norm Macdonald.”

These reactions sum up Macdonald’s distinctive character. He was unapologetically true to himself, projecting a keen awareness and always smiling with a look on his face like he knew something no one else in the room did. Even if he made fun of you, he did so in such a charming way that you couldn't help but laugh along.

Here are 10 memorable moments throughout Norm Macdonald's career.

'Weekend Update' - O.J. Simpson Coverage

While Macdonlad’s SNL tenure included many priceless moments, he’ll undoubtedly be best remembered for his stint behind the Weekend Update desk. From 1994-1997, the comedian brought his unique style to the anchor role, infusing the position with wry humor, sarcasm and a fair share of non sequiturs. Macdonald’s time as the Weekend Update host aligned with the so-called Trial of the Century, after O.J. Simpson was accused of murdering his ex-wife, Nicole Brown Simpson, and Ronald Goldman. Unafraid to ruffle feathers, Macdonald mercifully mined the trial for jokes, finding new and unique ways to label O.J. a murderer. Macdonald’s refusal to back away from such humor contributed to his removal from Weekend Update and eventual firing from Saturday Night Live.

 

'Billy Madison' (1995)

MacDonald’s SNL castmate Adam Sandler recruited him for the 1995 film Billy Madison. The flick, which saw Sandler as a slacker hotel heir who goes back to school to prove his worth, became an unexpected hit. Though it was Sandler who’d go on to become one of the biggest comedy box office draws in history, Macdonald stole nearly every scene he was in. As one of Billy’s loafing buddies, the comedian delivered such classic lines as “Who would you rather bone: Meg Ryan or Jack Nicholson?,” "You wanna feed that donkey some beer?," Now, now, maybe it's somebody else" and “Yahoo, Billy! Billy’s number one!”

 

Carrot Top Comments (1997)

As great as he was in scripted roles, Macdonald’s comedy truly shined when he could feed off of the natural reactions of another person. This made him the perfect guest for late night talk shows, with Conan O’Brien, David Letterman and Jimmy Kimmel all regularly welcoming him on their shows. During this 1997 stop on O’Brien’s Late Night program, Macdonald couldn’t help but butt in during another guest’s interview. Actress Courtney Thorne-Smith was on the show, explaining why she’d left the successful drama Melrose Place. When O’Brien asked about a film she’d shot with prop-comic Carrot Top, Macdonald dug in. “If it’s got Carrot Top in it, you know what a good name for it would be? Box office poison,” the comedian remarked. When Smith -- who, to her credit, seemed to take things in stride -- noted that the movie was called Chairman of the Board, Macdonald responded with, “I bet that board is spelled B-O-R-E-D.” Needless to say, Macdonald’s appearance was much more popular than the film.

 

'Dirty Work' (1998)

Dirty Work gave Macdonald his first feature film starring role, playing one of two buddies who set up a revenge-for-hire business. Though it was lambasted upon release, the flick has since developed a cult following. Comedy legend Don Rickles was among the supporting characters in the film, playing Mr. Hamilton, a curmudgeonly movie theater owner and the first victim of revenge. In a 2011 interview with Kimmel, Macdonald described working alongside the famed insult comic as “so awesome,” despite the fact Rickles regularly flubbed his lines and instead needed to be left to improv.

 

Introducing Artie Lange to Howard Stern (1998)

While promoting Dirty Work, Macdonald stopped by The Howard Stern Show. He brought with him his co-star in the film, Artie Lange. Macdonald gleefully told Stern about the antics in Las Vegas that resulted in Lange getting fired from Mad TV, including losing thousands of dollars gambling, doing cocaine and getting arrested. Lange’s wild shenanigans endeared him to Stern. The appearance led to Lange joining the show, replacing Jackie the Jokeman. Lange would stay with the hugely successful program for eight years, though he continued to struggle with substance abuse. The comedian always credited Macdonald for helping his career reach new heights.

 

Return to 'SNL' as Host (1999)

Macdonald was welcomed back to Saturday Night Live to host the episode airing Oct. 23, 1999. During his opening monologue, the comedian immediately addressed the elephant in the room. “I don’t know if you remember this, but I used to actually be on this show,” Macdonald slyly remarked. “So then, a year and a half ago, I had a sort of a disagreement with the management at the NBC. I wanted to keep my job. And they felt the exact opposite.” Macdonald went on to explain that he’d been fired because “they said that I wasn’t funny.” “But now, this is the weird part, right? It’s only a year and a half later and they asked me to host the show! So I wondered, I go, ‘Hey, wait a second here. How did I go, in a year and a half, from being not funny enough to be even allowed in the building, to being so funny that I’m now hosting the show? How did I suddenly get so goddamn funny?” Naturally, Macdonald answered his own question. “It occurred to me, I haven’t gotten funnier. The show has gotten really bad!”

 

Turd Ferguson (1999)

Arguably the most quintessential Celebrity Jeopardy sketch in SNL’s history, Burt Reynolds (Macdonald) went up against Sean Connery (Darrell Hammond) and French Stewart (Jimmy Fallon). While Connery certainly scored comedic points with his lines about Alex Trebek’s mother, the star of the scene was undoubtedly Macdonald’s Reynolds. The mix of arrogance and indifference, the constant gum smacking, the oversized foam cowboy hat, his insistence to be referred to by his new name, Turd Ferguson -- every part was gold.

 

Gift Basket for Conan (2010)

O’Brien’s brief and messy tenure as the Tonight Show host ended in January 2010. In one of the final episodes, Macdonald arrived as a surprise guest and brought with him a gift basket. The comedian explained that it was actually a present he had purchased seven months ago (when O’Brien started his ill-fated Tonight Show run) but that he’d simply forgotten to bring it with him during his previous appearances on the show. Macdonald then proceeded to read the card attached to the basket. “Congratulations, Conan, on finally securing your place as permanent host of the Tonight Show. That’s something they can never take away from you,” Macdonald deadpanned. “Sure, the pressure is on. But if I know you, Conan O’Brien, miserable failure is not an option.” The tone -- heartfelt, hilarious and sardonic -- was a perfect representation of Macdonald’s unique talents.

 

The Moth Joke (2014)

Another conversation with O’Brien delivered this gem from 2014. During his stop on Conan, Macdonald explained that his best material comes often from daily life, and that on the way to the show his driver told him a very funny joke. From there, the comedian meandered through a story about a moth who visits a podiatrist. The tale goes on and on, at times even getting quite dark. We won’t spoil the punchline that takes more than three minutes to get to, but trust us when we say it’s worth watching.

 

Last Appearance on Letterman (2015)

Fans were used to seeing Macdonald be cynical, silly and even occasionally rude, but on the final episode of the Late Show with David Letterman, the former SNL cast member showed his emotional side. Letterman had long been an idol of Macdonald’s, and the latter comedian was more than willing to pay his respects. During his set, Macdonald called Letterman the “the greatest talk show host who ever lived,” while also crediting him with helping jumpstart his own comedy career. Somehow, Macdonald managed to weave these heartfelt messages between jokes about LSD use, old-timey photography and Germany’s history in World Wars. Still, he was sure to end on a poignant note, choking up as he admitted the influence Letterman had on his life. “I know that Mr. Letterman is not for the mawkish, and he has no truck for the sentimental, but if something is true it is not sentimental, and I say in truth, I love you.”