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Norm Macdonald's Best Movie And TV Roles Ranked

The comedy world was dealt a devastating blow on September 14, 2021 when news came out that Norm Macdonald had died at the age of 61. He was a comedian's comedian, expertly threading the needle between dark humor and fringe comedy. To recognize that fact, all you have to do is watch one of the many talk show appearances he had. Even when other comedians were on the show, he'd find a way to have them bust up in hysterics. Without Norm Macdonald, the world's a little less funny.

However, Macdonald probably wouldn't want the world to feel too sad about his passing. A report by Deadline contains a quote from his long-time friend Lori Jo Hoekstra: "He never wanted the [cancer] diagnosis to affect the way the audience or any of his loved ones saw him. Norm was a pure comic. He once wrote that 'a joke should catch someone by surprise, it should never pander.' He certainly never pandered. Norm will be missed terribly.

In honor of that spirit, we'd like to look back at some of the most defining roles of his career. It's hard to narrow it down to a handful, but honestly, you could watch any Norm Macdonald movie or TV show and end up laughing uncontrollably.

Norm Macdonald got his own TV show in the late '90s

You know a comedian's made it when they get their own TV series where the name of the show is their own name. You have "Everybody Loves Raymond" starring Ray Romano and, of course, the recently released "Kenan" starring Kenan Thompson. One such sitcom that ended far too soon was the short-lived "The Norm Show," which kicked off on ABC in 1999. Later retitled to merely "Norm," Macdonald plays Norm Henderson, a former hockey player who's permanently banned from the league for various crimes, so he must undergo five years of community service. It's a cavalcade of comedic talent with a cast that also includes the likes of Artie Lange, Laurie Metcalf, and Ian Gomez.

Sadly, the show's tough to come by these days. It only lasted three seasons over the course of 54 episodes, and DVDs appear to be sold out almost everywhere. One of the streaming services would do well to remaster the series and make it available so that more people can witness Macdonald in all of his sardonic glory.

Macdonald could most recently be seen on The Middle

Despite the short lifespan of "Norm," the comedian didn't call it quits on sitcoms after that. He continued popping up here and there, and in 2010, he took on the recurring role of Rusty Heck on "The Middle." Rusty's your classic Norm Macdonald character. He's lazy, drunk, and smokes all of the time. He's also entirely unreliable, which frequently puts him at odds with his brother, Mike (Neil Flynn). 

Macdonald's last appearance in the middle came in the 2018 episode "Guess Who's Coming to Frozen Dinner." After the show ended, he'd go on to various voiceover roles in TV shows and films, including "Skylanders Academy," "The Orville," and "Mike Tyson Mysteries." Of course, Macdonald didn't need a script or a sitcom premise to prove how hilarious he was. He could riff off the top of his head and come up with pure comedy gold.

Norm Macdonald palled around with Adam Sandler in Billy Madison

"Billy Madison" is '90s-era Adam Sandler at his best. It's goofy, a little gross, but ultimately hilarious. Sandler plays the titular Billy, a spoiled rich kid who goes back to elementary school to prove to his dad that he deserves to take over control of his company. While he learns some lessons along the way, he's still pretty immature when all is said and done, as evidenced by him continuing to hang out with his two best friends — Jack (Mark Beltzman) and Frank (Macdonald).

Frank has many standout moments throughout the movie, like when Billy asks his friends what day it is, and Frank responds, "October." Or when Frank asks Billy if he'd rather have sex with Meg Ryan or Jack Nicholson from 1974. He may have been a slacker, but Macdonald brought his patented dry wit to the character to help elevate him above some of the other archetypes you'd find in movies of that era. If anything, it proved he would have a fruitful career in film in no time.

Norm Macdonald remains one of the best Weekend Update hosts ever

Norm Macdonald broke out into the mainstream as a featured player on "Saturday Night Live" in 1993. He was part of a fresh batch of faces that would define humor for the remainder of the decade alongside such giants as Adam Sandler, Chris Rock, and Chris Farley. But while a lot of the performers utilized grandiose, over-the-top caricatures, Macdonald was a different breed. 

He became synonymous with dry, sardonic humor. His delivery was often understated, and in many cases, it would take you a few seconds to realize what Macdonald just said was hilarious. Nowhere was this better encapsulated than his time as the Weekend Update host, starting in 1994. Behind the desk, he was able to do what he did best — deliver jokes as wryly as he could. And it was punctuated by one of the best running jokes in comedy history, which entailed Macdonald frequently making jokes about O.J. Simpson whenever he could, no matter how random it was.

Years after he started Weekend Update duties, Macdonald was abruptly fired in the middle of the 1997-1998 season (via Uproxx). It's become one of the most contentious points in "SNL" history, but luckily, we'll always have the clips to enjoy.

Norm Macdonald became a leading man with Dirty Work

Norm Macdonald often found himself in supporting roles, which tended to work best for his comedic sensibilities. But he proved he had what it took to lead his own project with 1998's "Dirty Work." Norm plays Mitch in the film, who, along with his best friend Sam (Artie Lange), realize the only thing the two are good at is enacting revenge on others. They start up their own company called "Dirty Work," where they'll mess with whoever you want ... for a fee, of course. 

"Dirty Work" wasn't exactly well-received when it first came out, but over the years, it's developed a cult following of sorts and is very much worth your time if you're a fan of Macdonald's brand of humor. In fact, Nathan Rabin wrote a piece about the movie for The A.V. Club in 2009, where he described the movie as "the ironic dumb comedy, the slyly postmodern lowbrow gag-fest that so lustily, nakedly embraces and exposes the machinations and conventions of stupid laffers that it becomes a sort of sublime bit of meta-comedy."

The comedy's available to watch on HBO Max, so don't let it pass you by. And as an honorable mention for the greatest Norm Macdonald roles of all time, make sure to check out his classic moth joke he did on "Conan."