Honestly, trying to rank the funniest Bill Murray movies is like trying to pick the best slice of pizza in New York. Everyone has a different "holy grail," and most of the time, the reasons we love them are totally personal. You’ve got the people who swear by the chaotic energy of the 80s, and then you’ve got the Wes Anderson devotees who think a raised eyebrow is more hilarious than a pratfall.
Bill Murray isn't just an actor. He’s a vibe. He’s that guy at the party who shows up uninvited, washes the dishes, tells a joke that changes your life, and then vanishes into the night. That weird, elusive "Bill Murray-ness" is exactly what makes his filmography so hard to pin down. Is he funnier when he’s being a total jerk, or when he’s being a deeply depressed oceanographer?
Basically, the answer is both.
The Improvised Chaos of the Early Years
If you want to talk about raw, unfiltered funny, you have to start with the era where Murray was basically just a live wire. Take Caddyshack (1980). Here’s a wild fact: Murray was only on set for six days. He didn't have a script. Harold Ramis just pointed a camera at him and said, "Go."
That legendary "Cinderella Story" monologue? Pure improv. He’s literally just muttering to himself while decapitating flowers with a golf club. It shouldn't work. On paper, it’s a weird guy in a bucket hat talking to himself. But because it’s Murray, it’s arguably the most quoted scene in comedy history.
Then you have Stripes (1981). This is peak "slacker Murray." He plays John Winger, a guy who loses his job, his car, and his girlfriend in one afternoon and decides the best solution is to join the Army. It’s the ultimate "anti-authority" movie. Most people remember the graduation drill, but the real magic is his banter with Harold Ramis. They had this effortless chemistry where they just looked like two guys who were way too smart for the room they were in.
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Why Groundhog Day is Actually a Dark Masterpiece
It’s impossible to discuss the funniest Bill Murray movies without hitting the big one: Groundhog Day (1993).
But here is what most people forget: the set was a nightmare. Murray and director Harold Ramis—who were basically creative soulmates—had a massive falling out during filming. Murray was going through a divorce and wanted the movie to be a philosophical exploration of the human condition. Ramis just wanted it to be funny.
The tension created something perfect. Phil Connors is a miserable, arrogant weatherman, and Murray plays that "jerk" phase with terrifying accuracy. But as the loop continues, the humor shifts. It gets dark. It gets weird. He kidnaps a groundhog. He commits "suicide" in a dozen different ways.
The movie works because Murray doesn't play it for laughs; he plays it for keeps. When he finally starts to become a "good person," it doesn't feel like a cheesy Hollywood ending. It feels earned. It’s the bridge between his "funny ha-ha" era and his "sad-funny" era.
The King of the Supporting Role
Sometimes, Murray is funniest when he’s only on screen for ten minutes. Take Kingpin (1996). His hair in that movie—that thinning, sweat-drenched comb-over—deserves its own Oscar. He plays Ernie McCracken, a professional bowler who is a total villain but is somehow more likable than the hero.
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He did the same thing in Tootsie (1982). He’s just the roommate, Jeff Slater. He wasn't even credited in the initial posters because he didn't want to mislead audiences into thinking it was a "Bill Murray movie." He just stands in the background, making deadpan observations that steal the entire scene.
And don't even get me started on the Zombieland cameo. Playing himself, pretending to be a zombie just so he can play golf without being bothered? That’s not just a movie plot; that is probably how Bill Murray actually lives his life.
The Wes Anderson "Murraynaissance"
Around 1998, something shifted. Rushmore happened.
Wes Anderson wanted Murray so badly for the role of Herman Blume that Murray agreed to work for a mere $9,000. He loved the script that much. This ushered in a whole new category of funniest movies—the ones where you laugh because everything is so awkward and sad.
- The Royal Tenenbaums (2001): He plays Raleigh St. Clair, a neurologist whose wife is cheating on him. He says almost nothing, and yet his face tells the story of a man who has completely given up.
- The Life Aquatic with Steve Zissou (2004): This is Murray at his most eccentric. He’s a washed-up oceanographer wearing a red beanie and carrying a Glock. It’s absurd, stylish, and oddly moving.
- The Grand Budapest Hotel (2014): Even in a tiny role as M. Ivan, he manages to anchor the whimsical chaos with that trademark dry delivery.
Ranking the Heavy Hitters
If you’re looking for a watchlist, you can't just look at Rotten Tomatoes scores. You have to look at the "rewatchability factor."
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- Ghostbusters (1984): Peter Venkman is the role he was born for. He’s a scientist who doesn't believe in science. He’s a hero who just wants to get paid.
- What About Bob? (1991): The chemistry between Murray (the needy patient) and Richard Dreyfuss (the ticking-time-bomb therapist) is legendary. Mostly because they apparently hated each other in real life, too.
- Scrooged (1988): It’s a cynical, loud, chaotic version of A Christmas Carol. It shouldn't be a holiday staple, but Murray’s Frank Cross is so deliciously mean that you can't help but love him.
- Lost in Translation (2003): It’s a drama, sure. But his performance as Bob Harris—doing those ridiculous Suntory whisky commercials—is some of his funniest work. "For relaxing times, make it Suntory time."
Why We Still Talk About Him in 2026
There’s a reason his movies haven't aged poorly. While other 80s comedies feel dated or "cringe," Murray’s humor relies on a specific type of detachment. He’s never trying too hard. He’s the king of the "deadpan," a style that is essentially timeless.
Whether he’s hunting a gopher or stuck in a time loop, he always feels like he’s in on a joke that the rest of the characters haven't figured out yet. It’s a rebellious kind of funny. It tells the audience that the world is a bit ridiculous, and the only way to survive it is to keep a straight face and a sharp tongue.
If you’re looking to dive back into his filmography, start with the stuff you haven't seen in a decade. You'll realize that Quick Change (the only movie he ever directed) is actually a hidden gem, or that his voice work in Fantastic Mr. Fox is better than most actors' live performances.
Your Bill Murray Action Plan
If you want the full experience, don't just watch one movie. Watch the evolution.
- Step 1: Watch Caddyshack to see the raw, unscripted energy of a guy who didn't care about the rules.
- Step 2: Watch Groundhog Day to see him perfect the "lovable jerk" archetype.
- Step 3: Watch Rushmore to see the moment he became an indie film icon.
- Step 4: Seek out Quick Change. It’s a heist movie where he’s dressed as a clown, and it’s criminally underrated.
The best way to enjoy a Bill Murray movie is to stop looking for the jokes and just watch his eyes. Usually, that's where the real comedy is happening anyway.