The Best and Worst of Matt Dillon

“The Best and Worst of” series chronicles the career highlights and lowlights of an actor starring in one of the week's new theatrical releases. This week, I take a look at the filmography of “Head Full of Honey” star Matt Dillon.

Films starring Matt Dillon that I've seen:
Drugstore Cowboy
There's Something About Mary
One Night at McCool's

Crash
You, Me and Dupree
Armored
Takers
Going in Style

Best Performance:  Drugstore Cowboy (1989)
Seeing Drugstore Cowboy nearly 30 years after its release has made me wonder why this didn't propel Dillon to superstardom. His raw, charismatic performance as the leader of a crew of young adults roaming around the Pacific Northwest robbing pharmacies to support their drug habits is the singular reason this character study ended up being such a haunting and enthralling watch.  

Worst Performance: You, Me and Dupree (2006)
Owen Wilson's overwhelmingly grating turn as the freeloading title character may overshadow him, but Dillion wasn't exactly great here either. As a stand-in for constant Wilson collaborator Ben Stiller in the straight man role, he seems to have absolutely no clue what he signed up for. Instead of serving as the voice of reason/reliable person to bounce jokes off of, he just looks super uncomfortable with  all of the zany antics that are going on around him.  

Best Film: There's Something About Mary (1998)
While The Farrelly Brothers early resume is loaded with gems (Dumb and Dumber, Kingpin, Me, Myself and Irene), There's Something About Mary is easily my favorite thing they've ever done. Outside of The 40-Year Old Virgin, no other movie I've seen has concocted a more stunningly effective cocktail out of gross-out sex/bodily fluid jokes, morbid situational comedy and legitimately heartfelt romantic sentiments.  

Worst Film: You, Me and Dupree (2006)
About eight years before The Russo Brothers became central figures in a little canon of films known as the Marvel Cinematic Universe, they burst onto the scene with an equally well-liked cultural touchstone in You, Me and Dupree. Of course since I'm a contrarian prick, I wasn't a fan of this revered classic. The hallmarks of a good buddy movie (chemistry between the leads, amusing banter, good-natured atmosphere) are completely MIA and as a result, all that's left are the ingredients for a well below average comedy driven by characters that are either dull or obnoxious.

Thank you for reading this week's edition of “The Best and Worst of”. The next victim of my praise and ire will be “Ben is Back” star Julia Roberts.