This one ended up being way harder than I thought it would, because there were just so many roles that came up. In fact, this was going to be a top ten list but that was just a list of classic comedy roles (hilarious sure, but not a lot of fun), and adding just five to the list didn’t give it enough snap. Twenty seemed good, but there were still so many great ones, that I ended up throwing in ten Honorable Mentions. Also in order to shoehorn extras in here and there I did have to cheat a couple of times and rank an ensemble cast as one role. If that truly bothers you, go write your own freakin’ list! Also, its important to remember that these are funniest ROLES, not funniest films.
ENJOY!
20 - Cooper Harris, EUROTRIP (2004)
Jacob Pitts portrayal of slacker best friend Coop makes the list almost entirely based upon the deadpan delivery Pitts brings to the role. Whether confronting what he thought was Scott’s coming out to him, blowing off his boss to go to Europe, or finally hooking up with Jenny on the plane ride home, Coop never looses his cool. Add in his signature quote, “This isn’t where I parked my car…” anytime he’s in a tight spot and he’s a comedy icon.
Best Scene: Coop’s trip to Club WanderSexxx.
19 - Alan, THE HANGOVER (2009)
Physical comedians will tell you that the number one thing you have to do to make the joke work is to commit to it, and in his breakout role, Zach Galifianakis goes way above and beyond the call. Sure everyone likes his crazy antics on the car ride to Vegas, and his speech to Doug started a cottage industry (www.wolfpack.com), but the genius of this role lies in the little things, such as his enthusiasm while hugging Eddie or his absolute insistence that tigers hate cinnamon. And its Galifianakis’ wide eyed portrayal of Alan that makes us not only believe him, but love him at the same time.
Best Scene: Driving into the desert for meeting with Mr. Chow.
18 - Coach Wally Rigg, NECESSARY ROUGHNESS (1991)
Usually cast as a stern but lovable guy in charge (see BIG, OPPORTUNITY KNOCKS, etc..) Robert Loggia is a comfortable face to most of us, so much so that he once did an orange juice add where the entire gimmick was that the kid would only drink his juice because it was Loggia telling him to do it. And in this role he got to take it a step further and be the wise-ass, take no prisoners yin to Hector Elizondo’s quiet Coach Gennero yang. The result was freaking hilarious, and enduring at the same time.
Best Scene: Rigg’s pre-game speech before the final game.
17 - Van Wilder, NATIONAL LAMPOON’S VAN WILDER (2002)
Crossing over from TV to film can be pretty tricky for most actors, but then most actors don’t get to jump into a role that is undeniably custom made for their talents. Ryan Reynolds’ star making turn as the ultimate college slacker provided not only decades of idiots like me quoting his shtick any chance I got, but also multiple direct to video sequels and prequels desperate to cash in on his popularity. And ultimately, what’s not to like about the guy, Van’s actually a genuinely good guy that likes to spread the party around. Plus he’s got a comedic timing that’s just about unbeatable.
Best Scene: Van’s evening with Gwen’s parents and their friends.
16 - Harry Dunne and Lloyd Christmas- DUMB AND DUMBER (1994)
So inseparable that I had to list them together, Jeff Daniels and Jim Carrey’s iconic performances are probably two of the most quotable characters of all time (“No, it’s a cardigan, but thanks for noticing!”). When it debuted, it was the third in a string of hits for Carrey (right behind ACE VENTURA: PET DETECTIVE and THE MASK) and he was quickly becoming Hollywood’s most bankable star, so perhaps pairing him with that other cop from SPEED seemed like an odd choice. When it hit though, these guys became everything that anyone was talking about, and rightfully so.
Best Scene: Tricking Sea Bass into picking up the tab.
15 - Mrs. White - CLUE (1985)
Long time fan favorite Madeline Kahn has had dozens of iconic comedic roles (see YOUNG FRANKENSTEIN, BLAZING SADDLES, ets…) but its her portrayal of the pale and tragic Mrs. White that stands the test of time. From opening frame to multiple endings, this film’s magic is performed completely by its ensemble cast, and while Tim Curry’s manic Wadsworth gets the screen time, its Kahn who steals the show. Aided by her complete mastery of the less is more approach to a scene, not to mention her ability to throw her voice from tiny to huge at any given moment, Mrs. White is still my favorite of Kahn’s characters.
Best Scene: Defining her hatred of Yvette.
14 - Dark Helmet - SPACEBALLS (1987)
Believe it or not, there was once a time when no one thought that George Lucas needed a kick in the junk, and therefore any spoof of his beloved STAR WARS would actually be an homage of sorts. Luckily for us, Mel Brooks was the man for the job, and lucky for him, Rick Moranis was a comedic genius. By spoofing one of the most visually iconic villains of all time, Moranis could have easily spent the movie behind the mask making breathing jokes and threatening people, but its when he lifts Helmet’s facemask that he’s funniest. And what better way to contrast Vader than a whining, glasses wearing little guy that pouts at almost everything. Comic Gold.
Best Scene: Playing with his dolls.
13 - Navin R. Johnson - THE JERK (1979)
Much like Kahn in the fact that Steve Martin could conceivably take up multiple spots on this list (in fact, I resisted the temptation to list two separate Martin characters in this one spot), this is undeniably his funniest role. Stealing liberally from his incredibly popular comedy routine, Martin made the jump from stage to screen at a time when it wasn’t a given that comedians would just do that. And from its opening scene to its wonderful ending, The Jerk is pure Martin zaniness the entire way. Some naysayers might say that he’s not really acting (and he is a long way off from the subtle charisma he’ll eventually develop for films like FATHER OF THE BRIDE) but that’s not the point, throughout the entire film, he’s still freaking hilarious.
Best Scene: Storming out of his house and taking the things he’ll need.
12 - Det. Axel Foley - BEVERLY HILLS COP (1984)
Known for his hilarious outbursts and raw standup routines, Eddie Murphy hit his stride when he portrayed the free styling Detroit cop that’s in town to check on a friend and gets involved in a murder investigation. Paired beautifully with stuffy Beverly Hills Detectives Taggert and Rosewood (played by John Ashton and Judge Reinhold), Murphy is allowed to bellow and laugh his way throughout the entire film. Everything from him getting thrown out of a building to his beautiful attempt at explaining the strip club shoot-out to Taggert and Rosewood’s Captain is a perfect vehicle for Murphy to exude Foley’s swagger and charm.
Best Scene: Visiting the art gallery with Bronson Pinchot.
11 - Sally Albright and Harry Burns - WHEN HARRY MET SALLY (1989)
Forever remembered for the orgasm scene, this film truly went after the issue of can two friends sleep together and remain friends in the morning long before network sitcoms where making it a weekly topic. And who better than Billy Crystal, then most known for his comic shows and Saturday Night Live, and Meg Ryan, already in the midst of her successful campaign for America’s Sweetheart, for us to latch on to. From the moment they’re paired up, Harry and Sally couldn’t be more different, and both of them think the other one’s nuts for the first half of the movie. But once they become friends, they generate the warmth for each other that makes these two such an endearing pair.
Best Scene: Discussing their day at the museum.
10 - Jimmy Dugan - A LEAGUE OF THEIR OWN (1992)
Tom Hanks, once again an actor that could own this list (BIG, TURNER AND HOOCH, BACHELOR PARTY, etc…), gives his best and most understated comedic performance as the sauced up manager to the Rockford Peaches. Spending the first half of the movie cussing his lot in life and drunk out of his mind, he eventually morphs into a true manager and protector of the girls he’s managing. But its Hanks’ incredible comedic timing that sustains the transformation throughout, as well as gives us some of the greatest scenes from a sports movie. Everything from teaching kids about STDs to politely insisting that Evelyn learn to hit the cut off man is hilarious simply because Tom Hanks is the man.
Best Scene: “There’s no crying in baseball!”
9 - Jim - BLAZING SADDLES (1974)
For a film that set the record of one joke every minute, almost everyone involved in this picture has an iconic scene to their credit (‘The Sheriff’s !”; “Numthim, eh?!”; and of course the famous campfire scene), but the standout is Gene Wilder as Jim, the Waco Kid. Perfectly complementing Cleavon Little’s Bart with understatement and aplomb, Wilder breezes through the film with that bemused look on his face, and ends up stealing the show right out from under everyone.
Best Scene: Jim’s introduction in the jail.
8 - Dr. Rumack - AIRPLANE! (1980)
Everyday when the sun rises, the Wayans brothers turn towards Hollywood and give thanks for the invention of the Parody Film, and when they do, they thank Jim Abrams and the Zucker brothers for this leap of comedic genius. And while its chocked full of famous performances (Barbara Billingsley as the Jive Lady!!) the one to beat is Leslie Neilsen as the unflappable Dr. Rumack. In what could have been a one joke performance (“and don’t call me Shirley.”) Nielsen makes Rumack funnier and funnier by simply remaining calm and delivering almost every line in a perfect comedic deadpan.
Best Scene: Sneaking into the cockpit during the landing for his famous line.
7 - Cousin Eddie - NATIONAL LAMPOON’S CHRISTMAS VACATION (1989)
After nearly stealing the first film away from Chevy Chase in only a few scenes, this is the film that made Randy Quaid’s Cousin Eddie infamous. From the moment he shows up till the moment their all out on the lawn singing the National Anthem, Eddie’s a madcap of stupidity and surprising heart. While he kidnaps Clark’s boss because he can’t get Clark anything else for Christmas and in a mad rage, Clark says that that’s the thing he wants most; he also challenges the validity of Clark telling the kids that the National Weather Service has spotted Santa on radar. That’s Cousin Eddie, and we wouldn’t have him any other way.
Best Scene: Shopping with Clark before Christmas.
6 - Tommy Callahan - TOMMY BOY (1995)
Taken from us way too early, as so many comedians seem to be, Chris Farley’s career defining turn as the lovable loser Tommy Callahan still rings as one of the funniest characters of all time. Joined at the hip to David Spade while on SNL, Farley racked up hit character after hit character and was known for his jovial characters suddenly going nuts and expounding at full volume (“in a van DOWN BY THE RIVER!!!!”). But when he made the jump to leading man in Tommy Boy, his biggest moments came when he used his boyish wonderment to provide earnest feelings. Not to mention that Tommy is one of the most quotable SNL characters to ever make it to the big screen.
Best Scene: Tommy’s disaster filled brake scenario in the sales meeting.
5 - Kelly - THE GIRL NEXT DOOR (2004)
When it came out in 2004, The Girl Next Door was this little comedy that was actually one of those movies that’s sum was greater the its parts. Sure it boasted mega-hottie Elisha Cuthbert as a porn star and a bitchin’ soundtrack, but it was buoyed further by a likable performance from new comer Emile Hirsch and an outrageously over the top turn from Chris Marquette as best buddy Eli.
But it was Timothy Olyphant’s role as Kelly the porn pimp that gave blew everything out of the water for this one. Prior to this film, Olyphant was best known for some minor roles in GONE IN SIXTY SECONDS and GO, but this is what vaulted him into the stratosphere as a true leading man. Kelly’s role could have been a completely unfeeling jerk, and from the moment he steps on screen, you don’t know what to make of him. But the beauty of Olyphant’s performance, whether friendly or diabolical, is that he does everything with complete confidence and doesn't waste a second thinking about how anyone will respond to him.
Best Scene: Visiting a strip club with Matthew and Danielle.
4 - The Channel 4 News Team - ACHORMAN: THE LEGEND OF RON BURGUNDY (2004)
Easily the hardest to rank in my list, not only because out of everyone else these guys are hands down the most quotable members of the group, but also because I’m totally cheating by lumping in all four of them into one slot. Nevertheless, the combination of Will Ferrell, Paul Rudd, Steve Carrell, and David Koechner as Ron Burgundy, Brian Fantana, Brick Tamland, amd Champ Kind will live in infamy as pure comedic gold. Produced as a throwaway summer comedy, Anchorman became a generational sensation when it debuted in 2004, not only boosting the careers of every single person in it, but also creating a viable presence for these types of films at every major studio.
And at the helm of the mayhem was Adam McKay, Ferrell’s longtime buddy and writing partner, who rightfully became a sought after writer-director following the films success. Introduced to us with a combination of voice over narration and fourth wall breaking direct talking to the camera, the Channel 4 News Team became an iconic comedy team, with everyone of them handily covering their area of the joke, these guys set a new bar in comedy.
Best Scene: The Street Fight Royal Rumble.
3 - Clark Griswold - NATIONAL LAMPOON’S VACATION (1983)
Creating an iconic character that will endure not only an entire career, but three separate sequels in two separate decades is no small feat, luckily Chase is no average actor. Almost making the list twice as the equally enduring Fletch (although in the end, I decided that Fletch is more cooler than cool than hysterically funny), Chase has made a career out of creating incredibly over the top performances from mundane situations. From his early days on SNL, to his current days on Community, Chase still has the market cornered on lovable loser striving to be the hero.
So it was that his performance as Clark Griswold, the hapless family man who allows his desire to give his family the ultimate summer vacation deteriorate into a kamikaze mission from hell, that puts Chase near the top of the list. Every moment that he’s on screen, Chase infuses Clark with so much manic energy that he’s just as funny while naively asking for directions in a ghetto as when he’s flirting with Christie Brinkley using a urine drenched sandwich. In the end, what makes Griswold so enduring is that he truly is doing everything he does all in the name of his family.
Best Scene: Clark finally losing it and taking the Wally World guard hostage.
2 - Miracle Max - THE PRINCESS BRIDE (1987)
Every once and a while a movie comes along and breaks away from conventional form only to become a generational icon. For everyone from my generation, that film was the Princess Bride, because I honestly don’t think that I’ve ever met anyone my age who’s never seen it. Plus, it has such an odd combination of action, comedy, and romance that makes it so unique. Held together by an impeccable cast that includes everyone from Columbo to a professional wrestler, Rob Reiner created one of the most enduring family films of all time with this wonderful fairy tale.
However, no matter how good everyone else was in this film, and they were all at the top of their game, no one lays a finger on the incredible Billy Crystal and his wonderfully over the top performance as Miracle Max. He’s only on screen for less than ten minutes, but every moment counts because he’s so freaking funny (set note: not only did Reiner have to leave the set during filming because Crystal was too funny, Miracle Max was responsible for the film’s only injury as Mandy Patinkin broke a rib trying to prevent laughing on set). Add in his pitch perfect report with Carol Kane as his wife, and Max stands at the top of the heap of iconic hysterical mythical witch doctors.
Best Scene: Examining Wesley (pretty much the only one he was in).
1 - Dr. Peter Venkman - GHOST BUSTERS (1984)
They say that necessity is the mother of invention, if so whatever necessitated Dan Aykroyd to write this gem of a movie deserves a long overdue thank you from millions of loyal fans. Thought of during production as a bit of an underdog with way too difficult of a plot to attract audiences, Ghost Busters did not generate the highest of hopes during its production. Those fears were soon put to bed, not only by the hype the fictional advertisement/teaser for the film created but also as it became a bona fide hit during the summer of 1984. The strength of the piece was the camaraderie of the three leads and how easily you believed that these guys could get together and do these things.
But it was Bill Murray’s performance of Dr. Peter Venkman (“I have degrees in psychology and para-psychology.”) that became the one to beat for funniest role. Played with equal parts aplomb and wise-ass disinterest as only Murray can do, Venkman is compulsively watchable the minute he steps on screen. While Aykroyd’s earnest portrayal if Ray gave the film its heart and Harold Ramis’ deadpan turn as Egon gave the film its believability, Murray delivered knock-out one liners again and again as the film just kept coming at you. To top it all off, Venkman’s absolute confidence that he is a lady’s man, all the while looking like Bill Murray in 1984.
Best Scene: Negotiating in the Mayor’s office.
HONORABLE MENTIONS: (not ranked)
Coach - SAVING SILVERMAN (2001) played by R. Lee Emery
Kirk Lazarus - TROPIC THUNDER (2008) played by Robert Downey Jr.
Broken Lizard - BEERFEST (2006) played by Jay Chandrasekhar, Kevin Heffernan, Steve Lemme, Paul Soter, and Erik Stolhanske
Barf - SPACEBALLS (1987) played by John Candy
Melvin Udall - AS GOOD AS IT GETS (1997) played by Jack Nicholson
Det. Phoebe Ohara - KINDERGARTEN COP (1990) played by Pamela Reed
Lenny Haise - THAT THING YOU DO (1996) played by Steve Zahn
Neal Patrick Harris - HAROLD & KUMAR GO TO WHITE CASTLE (2004) played by Neil Patrick Harris
Corky St. Clair - WAITING FOR GUFFMAN (1996) played by Christopher Guest
Derek Zoolander - ZOOLANDER (2001) played by Ben Stiller
