5. Polonius in Hamlet

Watching Bill Murray do Shakespeare is like… it’s like watching a dog do Shakespeare. Firstly you’re surprised that such words can come out of their mouth, and secondly you’re surprised about how goddamn entertaining it is. If only he was able to ad-lib somehow – that would be amazing. He does, however, play with his inflection and movements it seems – making the part oddly his. When he waves away Laertes with a “The time invites you; go!” it sounds positively Bill Murray.

Then again, it’s hard to tell if he takes so many pauses in his lines for emphasis or because he has to keep remembering them. Either way is probably fine; that Shakespeare shit is just hogwash. It’s not even real words.

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4. Frank Milo in Mad Dog and Glory

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This film comes with a bonus: not only does Bill Murray play a ruthless yet sarcastic mobster who roughs up a timid police officer, but that officer is played by Robert De Niro. That’s right, De Niro gets beat up by Bill Murray, and also has the most awkward sex scene known to man with Uma Thurman. Like, really awkward – think drunken dog having sex with a bag of snakes. This film is all kinds of confusing awesomeness, and yet nobody I bring it up to seems to know it exists – it’s like that movie where Julianne Moore and McNulty can’t find their kids and it turns out to be aliens.

This was directed by the guy who did Wild Things, which probably also deserves a nod on this list as it features Murray as a slime ball lawyer in a neck brace. It’s weird to think that you can have both lesbian make out scenes and Bill Murray in the same film, as those two concepts exist in very different parts of my brain.

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3. Happy Shannon in Passion Play

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In this 2010 film made by the same guy who wrote Scrooged and the aforementioned Mondo Video, Bill Murray plays what is probably the closest you could ever get to an unlikable character – an abusive mobster named Happy Shannon who is gunning for Mickey Rourke’s girlfriend, a winged showie played by Megan Fox. Yeah, that’s actually the plot.

While not perfect, a lot of people seemed to miss the point of this film. When it was first reviewed by Variety it was panned for having gaps in realism, and at least one critic walked out of its first hour at its Toronto International Film Festival screening. The irony of both events is that, if you actually watch the ending, the purpose of the film and its lack of realism are actually explained perfectly.

Again, I’m not saying this film was perfect, rather that – at least these days – it feels like if people don’t instantly understand what they are witnessing right away they completely turn on it. I think back to high school watching films like Wings Of Desire and The Illustrated Man and having an appreciation for the weirdness, and the art of that. It makes me wonder if the same people, people like myself who praise those films, would praise them if they came out today. Also I was stoned out of my grill in high school so that… that probably played into it.

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2. Ted Breughel The Sky Host in Nothing Lasts Forever

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This is as perfect of a rare and bizarre combination as it gets. The film, based on the book of the same name, was directed by Tom Schiller – a writer for SNL. It starred Lauren Tom and Gremlin’s Zach Gilligan and included Dan Aykroyd and our man Bill Murray. It was made in 1984 and never officially released to DVD. While occasionally there are showings, there’s not much else you can do to watch this film, which features Murray as a sinister bus driver for a magical bus that goes to the moon. Yeah, that’s the kind of film we’re talking about here.

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1. Johnny Blaze aka The Human Friggin Torch in Fantastic Four

This is so freaking weird that I wrote this entire list just to share it. Bill Murray was in a Fantastic Four radio show. Seriously that happened. ‘Twas 1975 and a young Bill Murray was mere months away from becoming a member of Saturday Night Live. Until then he would do work for the 10-episode Marvel Fantastic Four Radio Show, a show that you can listen to right here.

In it, Murray depicts the Human Torch exactly like you’d imagine it: like Bill Murray. It’s so not the right role for him, and yet who cares? Brilliance.

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