Bill Murray has a litany of films to his credit, ranging from comedies to some very dark dramas. My favorite Bill Murray films are invariably his funniest. Unlike some current big names in comedy, Murray has displayed significant range in his most popular comedies. See if you agree with the list below of the funniest Bill Murray films.

5. The Man Who Knew Too Little
This is a relatively obscure Bill Murray comedy from 1997. It made just under $5 million on its opening weekend but it stands as one of Murray’s funniest films. In this movie Murray plays a hapless American visiting his brother in England. In an effort to get him out of the house while his in-laws are visiting, Murray’s character (Ritchie Wallace) is signed up to ‘star’ in a ‘real life movie’ in which the participants are shuttled all around London pretending to be a tough character.
Of course, Murray’s character gets mixed up in some real life nonsense that almost gets him killed and all the while he has no idea. Be warned, this is a very corny comedy. I like it because it shows more of Murray’s silly side, which he doesn’t seem to favor these days. If you haven’t seen this film but love Bill Murray, I highly suggest you check it out, number five of Bill Murray’s top five funniest movies.
Notable Quotes: “Time out! Time out! I got something in my eye!” (While being shot at.) “Yo matey, you just stabbed me with your pen.” (After being punctured with sleep syrum.)

4. Rushmore
Rushmore was quite a departure from Murray’s more silly roles. Wes Anderson and Owen Wilson penned this film about a clueless high school (Max Fischer played by Jason Schwartzman) student who crosses paths with Murray’s character (Herman Blume) and they become friends. Unfortunately they also fall for the same girl who happens to be a teacher at Max’s school, the same school that Herman’s children attend. Like many Anderson films, Rushmore possesses a calm cuteness about it with endearing characters who often find it difficult to overcome their selfish tendencies to help others they love.
The humor here is slow, witty and sometimes a bit dark. The main characters are childish and selfish and it makes for great comedy. The jokes are not always explicit though and I have talked to many people who simply don’t think this movie is funny. I still think, for fans, it ranks as one of Bill Murray’s top five funniest films. When it was released it saw more than 16 straight weeks of over $10 million dollars from box office earnings.
Notable Quotes: Max: You think I got kicked out for just the aquarium? Nah, it was the handjob. And you wanna know something else? It was worth it.
Herman: You guys have it real easy. I never had it like this where I grew up. But I send my kids here because the fact is you go to one of the best schools in the country: Rushmore. Now, for some of you it doesn't matter. You were born rich and you're going to stay rich. But here's my advice to the rest of you: Take dead aim on the rich boys. Get them in the crosshairs and take them down. Just remember, they can buy anything but they can't buy backbone. Don't let them forget it. Thank you."

3. Caddyshack

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Many fans consider Caddyshack to be Bill Murray’s funniest movie. I definitely think it is in the top five. Chevy Chase is hilarious in the movie as well. I don’t think Murray is in the movie quite enough for it to be considered his very best. The character he plays (Carl Spackler) is possibly the weirdest and most unique he has ever played (Yes, I am including Steve Zissou). This is one of those movies where nearly every single line is a memorable quote (though not necessarily a funny one). If you haven’t seen it, watch it. If you have seen it, watch it again.
Notable Quotes: Spackler: “Cinderella story! Out of nowhere! Former greenskeeper, now about to become the Masters Champion!”
Ty: “I like you Betty” Danny: “It’s Danny sir.”

2. Ghostbusters
Ghostbusters is likely the most merchandised movie of the 1980s. Dan Aykroyd, Harold Ramis and Rick Moranis certainly make the film that much funnier. The box office take worldwide for Ghostbusters is over $280 million dollars. Murray plays a character who seems to be most like who he is in real life (or who I think he is). You have likely seen this film many times but it never hurts to watch it again. Rumors have run around that there may be another Ghostbusters film in the works (but I doubt it since that rumor has been floating for a few years now).
Notable Quotes: Spengler: Don’t Cross the Streams
Venkman: The flowers are still standing!

1. What About Bob?
Most fans would not agree that this is Bill Murray’s funniest movie.  I definitely think that Bob Wiley is the funniest character Bill Murray has performed. Richard Dreyfuss plays opposite Murray and is a bit stiff but that’s what his character calls for. The movie is corny and a bit over the top at times but I always find Murray’s character utterly hilarious. Unlike some of his more recent performances, Bob Wiley is a happy-go-lucky character with a litany of mental issues to deal with. Dreyfuss is his psychiatrist and loses his own mind a bit when Bob attaches himself to his family and they begin to sympathise with him. If you are thinking, “No way, this isn’t Bill Murray’s funniest movie.”
Notable Quotes: Bob: “Take a vacation . . . from my problems.”
Bob: “Baby step to four o’clock, baby step to four o’clock. . . “
Bob: “There are two types of people in this world: Those who like Neil Diamond, and those who don't. My ex-wife loves him.”

What do you think? Do you agree with this list of Bill Murray’s top five funniest movies?

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