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Owen Wilson's Best & Worst Films

October 21st, 2008 9:21am EDT | Dee Doyle By: Dee Doyle
Owen WilsonThe Frat Pack has been a powerful force in the new Millennium, and for awhile it was like we could not see a comedy without Ben Stiller, Will Ferrell, Vince Vaughn, Luke Wilson, and Owen Wilson. These comedic geniuses are quirky, timely, and have a lasting power that will keep them in movies for years to come. The goofy, charming Owen Wilson has proven himself not only as an actor, but as an Oscar-nominated screenwriter. There's a lot more going on beneath those blonde surfer bangs than one might expect, and with "Marley & Me" coming out this Christmas, let's take a look at some of the finest and worst Owen Wilson movies.

The Best

"The Royal Tenenbaums"

This cult classic won the heart of critics and audiences alike with its odd characters and dark sense of humor. It was written by Owen Wilson and Wes Anderson (their third movie after "Bottle Rocket" and "Rushmore") and starred Ben Stiller, Gene Hackman, Anjelica Huston, Gwyneth Paltrow, Luke Wilson, and Owen Wilson of course, among many other stars. It is a story about an eccentric family with three child geniuses (Paltrow, Luke Wilson, and Stiller) who find failure in their later lives after their father (Hackman) abandons them. This is a movie about his attempt to rejoin their lives for nefarious and/or heartwarming reasons. Wilson plays Eli Cash, the boy who is 'one of the family' and the best friend of Ritchie (Luke Wilson). He has always desired to be one of the Tenenbaums and finds a way by sleeping with Margot (Gwyneth). He only shows up a few times in the film, but each time is both hilarious and pathetic. Wilson's real stardom in this brilliant movie is the fact he co-wrote it and was nominated for an Oscar.

The Royal Tenenbaums



Wedding Crashers

The "Wedding Crashers" grossed over 200 million dollars in its theater run and shocked everyone by its lasting power. This along with "The 40-Year-Old Virgin" is considered one of the films that brought back the R-Rated comedy, which Judd Apatow dominates currently. The magic of this movie is in the form of its two stars: Owen Wilson and Vince Vaughn. Their incredible chemistry as John and Jerry had the audience falling out of their chairs laughing. Popular phrases and iconic sayings came from this film, like the term wedding crashers itself, which means people who come to weddings uninvited to pick up women and have fun. Wilson played John, the sweet hearted crasher who falls deeply in love with aristocrat Claire Cleary (Rachel McAdams). He cons his way into being invited for a family weekend which he and best friend Jerry (Vaughn) will never forget. This raunchy film was hilarious and yet heartfelt at its core, with an unbreakable friendship and a genuine romance. Wilson proves his laid back attitude can be lead man quality, and he actually plays straight man to Vaughn's insanity for once.

Wedding Crashers



Zoolander

Owen Wilson is a good looking guy, but could you really see him as a fashion model? Ben Stiller could, and that's why he ended up co-starring in "Zoolander." This movie is one of the funniest and silliest movies of 2001. It suffered slightly due to coming out soon after September 11, but in DVD sales and fandom it achieved a higher status. The movie is about male model Derek Zoolander (Stiller) and his midlife crisis due to the emergence of Hansel (Wilson) as a more popular model. He is secretly trained to assassinate a Prime Minister. Sounds insane? Absolutely. Wilson is hilarious as the peyote smoking model Hansel and the runway 'walk off' between Stiller and Wilson may just go down in history as one of the funniest moments in a comedy … ever.

Zoolander



Shanghai Noon

Jackie Chan often does movies where he partners off against someone very unlike him (see "Rush Hour" and Chris Tucker), and Owen Wilson fit that bill brilliantly. His easy going manner works as failing cowboy Roy, and although he is often typecast as this type of character, it really does work. Chon Wang (Chan) is trying to rescue the kidnapped Princess (Lucy Liu), and he becomes partners with Roy to do it. Chan and Wilson had enough chemistry to get a sequel out of this film, and it is one of the ways in which Wilson went from side character to full blown comic star. This was his big break movie, but it is his charm that sold him to audiences.

Behind Enemy Lines

Owen Wilson … the serious war action hero? Now that is a little strange to think of, but he did star in "Behind Enemy Lines" in 2001. This thriller movie is about a naval aviator named Chris Burnett(Wilson) who gets caught on the wrong side of the border during the Bosnian war. He is gunned down and manages to escape the Serbian army as they hunt him due to evidence in his possession. Gene Hackman stars as his commanding officer, and this movie was not exactly favored by the critics. It did not do exceptionally well, but Wilson's turn as a battered soldier trying to do the right thing was a surprising move for him. His performance proved that comedy isn't his only skill!

Behind Enemy Lines



The Worst

The Big Bounce

This is probably the biggest box office disaster of Wilson's career. It cost about $50 million to make and only made around 7 million in theaters. Ouch. Remade from a 1969 movie, it suffered with the same criticism as the original which was it deviated too much from the book it was based from. Wilson plays main character Jack Ryan who is a scam artist and gets lead back into danger by a beautiful woman (Sara Foster). He agrees to help her steal from her boyfriend Ray (Gary Sinise) and the usual bumbling scam attempt occurs. It had a pretty great cast with Morgan Freeman and Charlie Sheen also involved but generally suffered due to its lack of focus, real plot, or any character likeability.

Drillbit Taylor

This movie came out on the tail end of Wilson's depression, and maybe that would explain why he did it at all. He stars as the title character who is hired by a trio of nerds that want protection from a bully at school. His intention is to steal from the boys and run off to Canada, but he starts to like them and find self worth in himself, yadda yadda, seen it a hundred times. This is kind of like a light version of "Bad Santa." The movie proves that Wilson really needs a partner in the movie to bounce off of. His humor is at its peak when playing against someone else, and it just falls flat in an uninspired movie like "Drillbit Taylor."

Drillbit Taylor



I Spy

Eddie Murphy just hasn't had the best of luck in his starring roles lately, and "I Spy" is one of the examples of his poor choices. Special Agent Alex Scott (Wilson) is paired with middleweight champion Kelly (Murphy) in a mission to recover an invisible aircraft and … seriously that sentence should be enough to explain why this movie failed. A boxer. For a top secret mission. To get an invisible … you know what, no. Nothing else needs to be said. Wilson probably just wanted to work with Murphy, but this script should have tipped them both off early on.

Anaconda

There have been a lot of horror movies that try to get "Jaws" fame with killer animals on the loose. "Anaconda" was one of these low level films starring Jennifer Lopez, Ice Cube, Jon Voight, and Wilson played a supporting role. It is about a video crew filming along the Amazon River for a documentary that run into trouble when a giant vicious snake starts hunting them. They come across a snake hunter (Voight) who is trying to hunt the anaconda. Snore. This is a horror film with a few great moments of snake murder, but overall is kind of a dud. Wilson supplies some comedy relief and is actually one of the few characters people would've liked to see in the sequel (even worse). Okay, he was trying to make a name for himself before hitting it big. Everyone does a few bad horror films to start out. You're forgiven, Owen.


The Haunting

Here's another bad horror flick that Owen used to gain a foot in Hollywood. The unfortunate thing is that other celebrities followed his path that didn't need to like Catherine Zeta-Jones and Liam Neeson. This film is about a doctor (Neeson) who claims to be running an insomnia trial at a creepy old house. He really intends to study their reaction to fear, but things quickly go out of control when the ghost stories about the house turn out to be true. No one can leave the house, and Wilson plays insomniac Luke Sanderson. His death is actually the coolest of the film and one of the few real scary moments, but otherwise it used poor judgment in special effects and extremely cliché lines. It's a good thing for Wilson that Shanghai Noon came out the next year.


Dee Doyle
Story by Chelsea 'Dee' Doyle
Starpulse contributing writer