Top 5 Funniest Characters of The Last 30 Years

Because of the evolution of comedy since the beginning of cinema, this was a very difficult list to put together.  Comedy tends to go through phases and trends.  It has also stayed paradigm in many ways.  How do we compare the past to the present?  Take, for example, "It Happened One Night".  This was the beginning of light romantic comedy. How do you compare that with "Annie Hall", the first romantic comedy to deal with real issues? Or take "Arsenic and Old Lace", the most traditional of comedies and compare it to "Shrek" which spits in the face of tradition.  It just cannot be done. So, I am going to focus on the last 30 years of live action characters.  I also want it to be understood that there are dozens of characters that may deserve to be on this list, but I have to draw the line somewhere.  I desperately wanted to make this a "Top 8" because with Holly Hunter and Nicholas Cage as H.I. and Edwina McDunnough from "Raising Arizona", Will Ferrel as Buddy the Elf in "Elf", and Zach Galifianakis as Alan Garner in "The Hangover" this list would have been the most perfect list I have ever created.  But I have my principles, and in the words of the great Harry Waters (Ralph Fiennes in "In Bruges"), "You've got to stick to your principles."

5. Jason Schwartzman as Max Fisher- "Rushmore" 1998:

A great comedic character has a very specific recipe. That recipe is 1 part acting, 2 parts directing, and 3 parts writing. What makes this comedy so great is that we receive a five-part dose of Wes Anderson in one film.  As the writer and director he was able to put his unique style into every aspect of his characters.  The way Wes Anderson develops a character has done for comedy what Alfred Hitchcock did for mystery. He

gave it a complete reinvention. His new style will become a cinematic tradition that will carry on for years to come.  Comedy before Wes Anderson was, with few exceptions such as "Harold and Maude", about silly, campy, goofy laughs and we, the people, loved it.  We still love it.  However, Mr. Anderson took out the goofy and replaced it with the real.  His comedies do still have that slightly inane quality, but they also have an honesty about them.  He has created hilarious drama that does not subscribe to anyone else's brand of comedy.  His writing and directing style produces characters we relate to and characters that become more amusing each time we watch them on screen. He is always good, but his talent for character development is most flawless in "Rushmore".

Jason Schwartzman did a phenomenal job in his debut role as an elitist, loner high school student who falls in love with his young British teacher.  The dry and direct manner with which he delivers his lines gives his teenage angst an intelligence and flare exclusive to his character.  His complete self-confidence, equally admirable and irritating, is comical .  Though his superior manner can be grating we find ourselves rooting for this eccentric teenager, laughing at his back-handed compliments and cheering on his insulting tone. The audience's love for this humorous character derives from a recognition of how we were, how we wish we were, and how we wish we hadn't been in high school.  To follow in Max's straightforward footsteps I will end by saying this; his character is funny. Really, truly funny.

4. Marisa Tomei as Mona Lisa Vito- "My Cousin Vinny" 1992:

Funny actresses are a rarity in cinema.  Most comical roles for women are either poorly developed or developed to be completely unaware. However, Marisa Tomei nailed her Oscar winning role as a loud, Italian-American Brooklyn girl with a "Ticking biological clock". She is loud, opinionated and completely

completely ridiculous. But, she is funny.  Her comedic power comes directly from two sources.  The first is her ability to play off of her equally absurd co-star Joe Pesci who plays Vinny, her lawyer boyfriend who refuses to tie the knot until he wins his first case. She loves him.  She hates him. She helps him.  She hurts him.  No matter what she does she is funny.  The second source is the delivery of her lines.  Without a moment of hesitation, Mona Lisa Vito says what she means no matter how offensive or inappropriate.  She holds back for no one.  She is the perfect female character because she does not lean on the film for support, she makes us laugh all on her own.

3. Chris Farley as Tommy- "Tommy Boy" 1995:

1978- 1988 may have been the greatest decade for comedy in history. It was the heyday of the likes of Bill Murray, Dan Aykroyd, John Belushi, Whoopie Goldberg, Bill Cosby, and Steve Martin to name a few. It

produced gems like "Ghostbusters", "The Jerk", "Animal House" and "Caddyshack".  Then it was gone, as quickly as it came it vanished.  Then something beautiful happened. That great, campy genre of comedy was briefly resurrected with "Tommy Boy".  Triumphantly, the comedians finally took back their territory, if only for a moment.

What makes Tommy a fabulous character in the world of comedy is that he has a charming underdog quality that we root for.  We find that ridiculous personality type tender.  He is that character that messes up again and again for our entertainment, but once he finds his voice he saves the day in his own unique way for our satisfaction.  We get lots of laughs along the way and a feeling reminiscent of the golden age of comedy.  However, the main reason he receives the honorable #3 position is that thanks to "Tommy Boy" every time an adult sees a child's jacket lying on a chair the world gets a reenactment of "Fat Guy in a Little Coat".    

2. Mark Wahlberg as Tommy Corn- "I Heart Huckabee's" 2004: 

If you haven't seen this movie you may not believe that this stoic action hero with the rippling biceps could pull off a truly humorous role, but he most certainly can. Wahlberg plays a firefighter that hires existential

detectives after 911 to help him understand "How come we only ask ourselves the really big questions when something bad happens?"  Determined not to use petroleum, because if you do "you are a murderer, that's a fact", he rides his bike everywhere, even on the job.  After befriending Albert Markovski, another brilliant role by Jason Schwartzman, they become obsessed with "the cracks and the pain and the nothingness, because THAT's more real" to them then their original philosophy that "the universe is an infinite sphere whose center is everywhere and whose circumference is nowhere".  All of this may seem dark and joyless, but the absurdity of his character is endearing and comical.  Tommy Corn loses his center and in doing so he is able to completely be himself, a man trying to understand his place in the world, innocuously and sincerely. He becomes the offbeat individual that is inside of a us all.  Watching Tommy is like looking in a mirror, and it is that subconscious self recognition that is truly hysterical.

1. Bill Murray as Bob Wiley- "What About Bob" 1991:

Bill Murray, the quintessential every man, must be represented on this list of "Top 5". He is brilliant. A comedic genius. I have never seen him in a role I didn't love. His vulnerability on screen is alluring and

simultaneously disenchanting. He has a great gift for honesty, be it beautiful or ugly. He will display truth when truth is needed and when it isn't needed he shows us a good time with good ol' fashioned jesting. Finding his number one role as an actor is nearly impossible. How was I to choose between "Lost in Translation", "The Royal Tenenbaums", "The Man Who Knew Too Little", "Ghostbusters", and "Groundhog Day"?  Becuase of my previously mentioned principles I did choose. I chose "What About Bob" for three reasons.  Reason #1:  Quotability.  One of the most quotable comedies of all time. I could say any line from this movie in a group and I will get big laughs.  For example: "Isn't this a breakthrough, that I'm a sailor? I sail? I sail now?" or "Hi, I'm Bob. Would you knock me out, please? Just hit me in the face." It is just good stuff.  Reason #2:  Body language.  This is one of the most physically humorous movies out there.  The way he leans in and gets too close to the already agitated Dr. Marvin (Richard Dreyfuss) while begging him to treat the Turrets Syndrome that he doesn't have is perfect.  Or, the way he can't look while teaching Dr. Marvin's son, Sigmund, to dive because of his own anxieties. It is classic.  Reason #3:  Feel Good-ability:  That's not a word.  However, the principle is present.  There is nothing sad or dark about this comedy and when it comes right down to it that is what comedy is about.  It is about feeling good, laughing and enjoying a little bit of gaiety, and there is no one in the world more qualified to give us that then Bob Wiley.