Top 10 Funniest Movies – The 00’s

Article by Terry Plucknett

Posted - 10/21/09

Go to Top 10 Funniest Films List

There is a difference between comedies and funny movies.  I want to start by saying that.  There are many amazing comedies like Sideways and Lost in Translation that are more cleverly funny with great stories.  That is not what we are interested here.  We are interested in the movies that make you laugh the hardest.  There are the films that may not necessarily be the greatest films ever, but you will quote them forever.  With that said, here are the movies I find hilarious no matter how many times I watch them.

Honorable Mention – Evolution (2001), Kiss Kiss Bang Bang (2005), Shoot ‘Em Up (2007), I Love You, Man (2009), Stranger Than Fiction (2006), Grindhouse (2007)

10.  Leatherheads (2008).  This is one of the most unique comedies of the last 10 years.  It is set in the 1920’s and chronicles the struggles of a professional football league.  Not only is this when it is set, but it also is a throwback to slapstick comedies of the 30’s and 40’s.  George Clooney, John Krasinski, and Renee Zellweger form your typical, classic love triangle and hilarity ensues.  You forget that this is a film from this decade and start to think you are watching a classic Cary Grant film such as Bringing Up Baby or His Girl Friday.  Clooney radiates classic Hollywood more than anyone working today.

Carter Rutherford (Jon Krasinski): These are a lot like your plays, only a little more . . . effective.

9.  Keeping the Faith (2000).  “So a priest and a rabbi walk into a bar…”  We have all heard this start to a joke before, but this film plays out what this joke means.  Ben Stiller is the rabbi and first-time director Edward Norton is the priest and they are best friends that fall in love with the same woman, the hilarious Jenna Elfman.  It is a love triangle where both men technically can’t have the girl because of their office, Stiller because she is not Jewish and Norton because of his oath of celibacy.  The situations surrounding the love story, as well as the bizarre friendship between the two leads, bring about some very funny moments, including the two going shopping for a karaoke machine.  Check it out if you haven’t seen it.

Indian Bartender (Brian George): May those who love us, love us. And those who don't love us - may God turn their hearts. And if He cannot turn their hearts, may he turn their ankles, so that we may know them by their limping.

8.  Juno (2007).  The only Oscar-nominee on my list, Juno brings out a very good indicator of a funny movie: quotability.  Diablo Cody’s script brings out a Juno McGuff character that takes everything with a light-hearted, sarcastic sense of humor that you can’t help but laugh at.  Michael Cera is equally funny as the love interest.  However, my favorite characters are played by two character actors that have emerged in several hilarious roles throughout the decade: Allison Janney and J.K. Simmons who play Juno’s parents.  Simmons is my favorite.  Just the simple tone and inflections in his voice as he utters a line makes me laugh every time.

Bren (Allison Janney): Doctors are sadists who like to play God and watch lesser people scream.

7.  Knocked Up (2007).  The first, but definitely not last, appearance by the Judd Apatow crew on the list brings Apatow’s second directed movie and the emergence of one of the funniest people in film right now in Seth Rogen.  His ability to portray the average Joe with a heart of, well, slightly tarnished gold, has become a staple of Apatow inspired movies.  The whole group is on top form in this film, including Katherine Heigl, Jonah Hill, Jason Segel, Leslie Mann, Paul Rudd, and Jay Baruchel.  Not to mention the cameos from Ryan Seacrest, James Franco, and Steve Carell.  Apatow finds the happy medium between inappropriately hysterical and kind-hearted.  The best laughs in this film, though, come when the roommates are sitting around and just adlibbing insults back and forth at each other.  Well, either that or a road trip to Vegas and a hotel room with a variety of chairs.

Pete (Paul Rudd): Marriage is like a tense, unfunny version of Everybody Loves Raymond, only it doesn't last 22 minutes. It lasts forever.

6.  Walk Hard: The Dewey Cox Story (2007).  I really was not expecting this to be as funny as it ended up being.  However, this fictional story making fun of every music biopic ever made is hilarious from start to finish.  John C. Reilly is perfect as the title character who is part Johnny Cash, part Bob Dylan, and part insane.  He goes through many phases in his career, including a variety show host like Sonny & Cher and going through a hippie phase with the Beatles, portrayed as over-the-top as humanly possible by Paul Rudd, Jack Black, Justin Long, and Jason Schwartzman.  However, the funniest parts of this film come from the all-original songs that are on par with the best in comedy music.  Each song is different yet hilarious and perfect in its context of the story.

George Harrison (Justin Long): I just sit here while my guitar gently wimpers.
Paul McCartney (Jack Black): Well you are the quiet one so why don't you shut the fuck up!
Ringo Starr (Jason Schwartzman): I wrote a song about an octopus.
John Lennon (Paul Rudd): Jam it up your ass. You're lucky we still let you play the drums!

5.  Forgetting Sarah Marshall (2008).  This is the best of movies made by the Apatow cew, but not Apatow himself.  This film, written by Jason Segel, stars Segel as a musician trying to get over a bad break-up with his ex-girlfriend.  He goes to Hawaii and runs into her on vacation with her new boyfriend, played by Russell Brand in his introduction to the U.S.  Segel is hilarious, as is Brand.  The supporting characters played by some familiar names to this list, Jonah Hill and Paul Rudd, add to the craziness.  However, just like Walk Hard, the best part of this film is the music, including several shocking numbers performed by Brand’s fictional band, Infant Sorrow.  The highlight of the movie is “Dracula’s Lament,” a song performed by Segel that is from a puppet Dracula musical he is writing.  It is moments like this that make Jason Segel my favorite of the Apatow clan.

Aldous Snow (Russell Brand): I've lost a shoe... have you seen it anywhere? Excuse me, missus, I've lost a shoe... like this one. It's like this one's fellow... it's sort of the exact opposite in fact of that - not an evil version but just, you know, a shoe like this... but for the other foot. Otherwise I'd have two right...

4.  Bandits (2001).  This is my guilty pleasure of the decade that I find endlessly hilarious and quotable.  Bruce Willis and Billy Bob Thornton are bank robbers that escape from prison and continue their criminal waves in their own unique way.  Their character quirks are what bring about the laughs.  Willis is instinctive, while Thornton is overly-cautious.  They both fall in love with Cate Blanchett, and she falls in love with each of them for their very different quirks.  This film may have more one-liners than any movie on this list as well.  It’s just fun stuff.

Terry (Billy Bob Thornton): Beavers and Ducks!

3.  Inglourious Basterds (2009).  In what might be the funniest and most entertaining Tarantino movie, Inglourious Basterds is the only representative on my list from this year, but it deserves it.  It is a fictional account about a group of World War II soldiers who take it upon themselves to slaughter and kill as many Nazi soldiers as possible.  The entire cast is spot-on perfect, led by Brad Pitt, whose accent will make you laugh every time he speaks.  This, along with Grindhouse, were possibly the most entertaining movie-going experiences of the decade for me.

Lt. Aldo Raine (Brad Pitt): Bonjourno...

2.  The 40 Year-Old Virgin (2005).  The first Apatow-directed movie is still his funniest.  Steve Carell plays the title character.  His quirkiness is enough to carry a film, but we add in Seth Rogen, Paul Rudd, Romany Malcow, and Jane Lynch giving him advice and the very funny Catherine Keener becoming his love interest, you have pure comedy gold.  My favorite scene of the entire movie is just like my favorite scenes from Knocked Up.  It is just guys sitting around adlibbing for an extended period of time.  In this case, it is Paul Rudd and Seth Rogen making fun of each other while they play video games.  Just delightful.

Andy Stitzer (Steve Carell): I'm gonna tell her.
Cal (Seth Rogen): You should totally tell her.
Andy Stitzer: I'm going to.
Cal: 'Cause I watched this movie called Liar Liar and the message was, "Don't lie." And that was a smart movie.

1.  Anchorman: The Legend of Ron Burgundy (2004).  “You stay classy.”  “I’m kind of a big deal.”  “I don’t speak Spanish.”  “It’s a deep burn.  I don’t know if you were paying attention, but I did over 1000.”  “I could be wrong, but I believe diversity is an old, old wooden ship.”  “I just ate a big red candle.”  “They’ve done studies.  60% of the time it works every time.”  “Newsteam assemble!”  I could continue, but I would just quote the entire movie.  I even quoted this film in my write-up on The 40 Year-Old Virgin above.  This is the movie that just keeps on giving.  Will Ferrell’s best by far that he keeps trying duplicate and comes up short.  Great performances, once again, by Paul Rudd and Steve Carell along with others, add to the absolute ridiculousness of everything this movie is about.  From shameless womanizing to a newsteam rumble, this film is as classic as Ron Burgundy himself.  How could I not make this number one on my list?

Brian Fantana (Paul Rudd): Ron, where are you?
Ron Burgundy (Will Ferrell): I'm in a glass case of emotion!