This list was a suggestion from my only reader, so, as they say, “give the person what the want!” I will say it was an enjoyable list to think up, reminiscing about the movies, characters, and lines that most made me laugh. A couple of things about this:
Humor is inherently subjective, so funniest has an implied “in my opinion” to it.
Also, a movie’s reception can change as individual people change and as society changes with what is acceptable. Humor is perhaps the most susceptible genre to people going back an adjudicating what is okay and what is not. With that in mind, I tried to remember my reaction at the time, as well as whether these characters hold up.
I will try and link to a scene where possible that exemplifies the character.
This post is about the funniest movie characters, not necessarily the funniest movie or the funniest ensemble of characters. I imagine it’ll tilt a bit toward movies with one dominant main character.
Also, will tend to favor lead comedy performances. Screen time is a blessing and a curse, but there are plenty of random supporting parts that have less than 10 minutes on screen who steal the show. Generally, I stayed away from those.
SPOILERS of course. People don’t worry about spoilers with comedy as much, but who wants good jokes ruined?
Anyway, on to the list!
The most honored of honorable mentions: As with the last post, I have to throw out 2 honorable mentions at the top, based on a technicality. These are the funniest movie characters, and even though Borat (Sacha Baron Cohen) and Eric Cartman (Trey Parker) were both in a movie, and were very funny, I became aware of both characters from their TV shows, and therefore walked into the theater knowing I thought those two were funny. For that reason, I have to leave them off this list.
10. Derek Zoolander – Ben Stiller, Zoolander
I was late to the game on Zoolander. It was one of those movies that everyone was quoting and acting out early in high school, and by the time I had seen it, everything was kind of played out for me. Flash forward 8 or 10 years and I watched it with some buddies, I believe shortly after college, and I thought Zoolander was awesome.
Zoolander might be the first time I remember a movie being centered around a character who was actively dumb, maybe Bill and Ted, but they were high school kids, it just felt different. Derek was an actual adult, with a loft in New York City, who was stupid, just a vain, flaky “model idiot”. At the same time, he takes himself and his modeling career seriously, a living satire of the overemphasis we put on human beauty, and how good-looking people actually get to live a better life because of their looks, whether or not they’re a model.
One thing about Ben Stiller is that I think he is a really underrated actor. He does more serious roles now, which might get him a bit more respect, but the thing with Derek Zoolander or White Goodman or Tony Perkis is that 1) Stiller goes all the way, and 2) It’s a full character, his reactions in all situations are the reactions of the character. More on this at a later date, but I don’t get why character work like this doesn’t merit more Oscar consideration?
9. Susan Cooper – Melissa McCarthy, Spy
Melissa McCarthy is very funny, and it was hard to choose which role of hers was my favorite. The Heat, is very funny, Bridesmaids was the first time I’d ever seen her, but I like her in Spy because we get to see multiple versions of McCarthy. Early on, she’s the nervous, self-effacing person who stuff happens to, and then later when she’s undercover, she starts being the mouthy, aggressive alpha, similar to her character in The Heat. She also plays the straight woman at times to Jason Statham and Peter Serafinowicz. There is also a fair amount of physical comedy in the role. That versatility is great because it gives us multiple reasons to find her funny.
McCarthy’s bold confidence tends to be what makes me laugh the most. In Spy, she’s barking at billionaire arms dealers, making people cry, and fighting. When she gets backed into a corner, she turns up the aggressiveness and starts attacking.
It was hard to pick, which role for McCarthy, but I think she has the most time on screen here, the most different personas, as well as the most laugh out loud moments. I also think that overall it’s the funniest movie she’s in.
8. Beanie – Vince Vaughn, Old School
You were expecting Luke Wilson? It was very difficult to pick between Vince Vaughn and Will Ferrell in this movie. Both are hysterical. For me, the edge goes to Vaughn because it was the first time I saw him and his fast-talking sarcasm, and it was a thing to behold. I watched Ferrell on SNL and loved him, so although he was awesome it was semi-expected. Beanie was a dick, and nearly everything out of his mouth was funny.
This is where “ear muffs” came from. He’s also responsible for “…Columbus wasn’t looking for America my man, but that seemed to work out for everyone, didn’t it? You’re here.”
When we first see Beanie he is on the altar at Frank’s wedding, semi-berating Mitch (Luke Wilson) for not being appreciative of how “sexually enlightened” his ex-girlfriend was – the one who had literally just cheated on him and broke his heart. When Frank, the groom, interjects to thank them for being there, Beanie redirects his venom at Frank, chastising him for making the poor decision to get married. “You need to walk away from the A-S-A-P…”. Once the bride and her father are down the aisle, Beanie shakes the father’s hand and drops, “it takes man to give away an angel.” While the priest is talking he coughs “Don’t do it!” and coughs again.
It’s just non-stop one-liners out of Vaughn for the whole movie. He’s the man with the plan. He’s the one who decides to start the fraternity, he’s hosting pledges at the house without Mitch there. He’s thinking about the kick-off party. Beanie is constantly moving forward, and if you don’t like or understand what he’s doing, he’ll talk you into it. He’s also “surprisingly good at paperwork.”
7. Ace Ventura – Jim Carrey, Ace Ventura: Pet Detective
Eight year-old me can’t believe it! Ace Ventura was my guy! His faces, movements, and voices, he was ridiculous. His silliness may only be 90% as funny as it was in the 90’s, but the jabs and sarcasm still hold true. I do that move he does with the sliding door whenever I’m near a sliding door. If I’m eating with my family, I make sure my sister is watching me, and then I’ll show the food I’m chewing to my mother or father, when they aren’t looking – just like Ace does at the party! I’m an adult!
Ace Ventura is just a bizarre guy, with a rare, if unrealistic profession, that lands him in the middle of a criminal conspiracy that actually plays pretty well as just a noir-ish mystery movie.
Jim Carrey was very big, comedically. There wasn’t a ton of subtlety. He’s chloroforms a former member of the ’84 Miami Dolphins to see if his AFC Championship ring is missing a piece that he thinks he found at the scene of the crime. He runs around in a tutu, pretending to be crazy so he could get access to files at a medical facility. At the end of that video above he’s hip thrusting as a celebration in front of other adults. This is Carrey’s biggest and craziest performance. There is no other character like Ace, and he’s still one of the funniest people ever. Carrey has other funny movies, but unfortunately it was going to be hard to top his breakout role.
6. Willie (Santa) – Billy Bob Thornton, Bad Santa
This movie came out of nowhere, and for that, I’ll always probably have it on a pedestal. I was generally pretty attuned to what movies were coming out, and I remember it was Thanksgiving weekend, I hadn’t heard of it, my buddies and I go see it and it is in my top 5 hardest laughs in a movie theater.
It may seem somewhat obvious now, but this Santa just being ruthlessly mean to kids was, and still is, very funny. It just kind of comes out of nowhere each time, and even though you know the general principal, what he ends up saying is so much harsher than you’re expecting.
Juxtapose that with the kid. I felt so bad for that kid I almost cried a few times in the theater. But as bad as I felt, hearing Billy Bob yell, “what is your deal?” gets me every time. The consistent severity of everything he says is just unparalleled. I think watching someone be either mean or sarcastic with children in a fake world, with no actual negative repercussions for the children, will just always be funny to me.
5. Alan – Zach Galifiankais, The Hangover
“Are you ready to let the dogs out?” Another breakout role, most of the world was not familiar with Zach Galifianakis. I was a fan of his standup, but never saw this coming. He is the ultimate wild card, as Alan.
He’s mean to old men and children; he roofies his friends’ drinks; he makes a baby pantomime masterbating.
Every reaction he has is completely unexpected, and particularly when few knew Galifianakis, his jokes and oddities hit big. As I write this, #5 seems too low…
4. Dr. Evil – Mike Myers, Austin Powers Trilogy
Dr. Evil’s voice is perhaps the most fun impression to do around the house. Mike Myers is a brilliant physical comedian, and we get to see that in Dr. Evil’s physical stiffness, and occasional athletic outburst, like when he dances to “Beyond The Sea”. He has a ton of attitude and often mocks his colleagues (subordinates?)
Much like many of the James Bond movies they’re spoofing, this trilogy is epic because the villain is as good as the hero. Austin Powers is very funny and enjoyable, but if Dr. Evil wasn’t his equal, both in terms of savvy and silliness, we wouldn’t want him to ever be on screen.
It’s difficult to explain why Dr. Evil is so funny beyond his inherent goofiness, and sort of insecure confidence. He’s a brilliantly played satire of James Bond super-villains, where although he asks for ransoms, he’s mostly evil for evil’s sake. More than the money, he just seems to be obsessed with villainy.
3. Les Grossman – Tom Cruise, Tropic Thunder
So this was the one rule-bender. Les Grossman probably has less than 10 minutes of screen time, and he is not the main attraction in this movie, a very funny movie, by the way. But Tom Cruise is throwing heat. It might be the most heat anyone has ever thrown. It’s the same intensity we see in Mission Impossible VI when he’s running to to catch a plane that’s in the process of taking off. Other side characters come in, make a joke or two and disappear. Les Grossman comes in and, to borrow his phrasing, scorches the earth.
Tropic Thunder is a very smart and funny movie satirizing Hollywood, and Grossman is, somehow, the funniest, and most memorable character in a movie in which Robert Downey Jr. does blackface. He is a force of nature, something that doesn’t usually track well in comedy, but like I said, force. of. nature.
2. Dale Doback – John C. Reilly, Step Brothers
Step Brothers is also in my top 5 hardest laughs in a movie theater. Every scene in that movie his hilarious. It’s a hysterical concept, with two hilarious lead actors, and multiple funny supporting actors. Which brings me to Reilly vs Ferrell.
I was first exposed to Reilly in this duo’s first movie together, Talladega Nights. He was damn funny in that, but Ferrell is definitely the lead in that movie. In this movie, they’re equals, and they’re battling for supremacy. The Ringer’s Sean Fennessey said in a podcast about this very movie that there’s something that’ll always be funny about stupid people who think they’re smart. That’s why Reilly gets the edge over Ferrell here. Dale is more confident and less apologetic than Brennan. He thinks he’s that much smarter, and has an answer for everything.
When you think about it, this movie could easily be a hardcore drama. A widower and divorcee are both hampered by their 39 year-old deadbeat sons, who have had a hard time growing up and moving on. It brings them together and then drives them apart. If Dale and Brennan were addicts, it’s not funny; if they’re criminals, it’s not funny; even if they were just confused screw-ups, it’s mildly funny, at best. It’s the brashness behind everything they do and say that makes it a comedy. And Dale is the brashest.
1. Ron Burgundy – Will Ferrell, Anchorman
It’s easy to forget this now since this movie has been so over-quoted and over-impersonated that it lost some of its freshness. I was 17 when this came out, and for a few years, quotes form Anchorman were basically how my friends and I communicated.
There is so much potential for re-watch with this movie because the first time you see it you laugh at all of the obvious parts and miss some of the more subtle lines, which you pick up on repeat viewing.
It’s a great ensemble cast, but “Papa Burgundy” is king. He is the most heavily quoted and celebrated of the bunch, and for good reason. He kind of wins the funny guy decathlon here without maybe being the most extreme version of any characteristic in the movie. He’s dumb, but not as dumb as Brick; clueless, but not as clueless as Brian; crazy and belligerent, but not to the extent Champ is. And so on and so forth. He is a character of extreme characteristics, but the propensity for the extreme to be irritating is neutralized by the rest of the news team.
I probably thought this in 2004, and I think it now, Ron Burgundy is the funniest movie character of all time.
Honorable mentions: Megan – Melissa McCarthy, Bridesmaids; Detective Shannon Mullins – Melissa McCarthy, The Heat; Jeremy Grey – Vince Vaughn, Wedding Crashers; Steven Stifler – Seann William Scott, American Pie franchise; White Goodman – Ben Stiller, Dodgeball; Tony Perkis – Ben Stiller, Heavyweights; Lloyd Christmas – Jim Carrey, Dumb & Dumber; Kirk Lazarus – Robert Downey Jr., Tropic Thunder; Walter – John Goodman, The Big Lebowski;
Austin Powers – Mike Myers, Austin Powers franchise;
Tom Callahan – Chris Farley, Tommy Boy; Al Czervik – Rodney Dangerfield, Caddyshack; The Joker – Heath Ledger, The Dark Knight; Deadpool – Ryan Reynolds, Deadpool; Tony Stark – Robert Downey Jr., MCU; Daniel Hillard/Mrs. Doubtfire – Robin Williams, Mrs. Doubtfire; Ricky Bobby & Cal Noughton Jr. – Will Ferrell & John C. Reilly, Talladega Nights; Chazz Michael Michaels – Will Ferrell, Blades of Glory; Chazz Reinhold – Will Ferrell, Wedding Crashers
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