Review by Derrick Carter

Running Time: 2 hours 6 minutes

MPAA Rating: R for Language, some Strong Sexual Content and Nudity

Sideways poster

Directed by: Alexander Payne

Written by: Alexander Payne & Jim Taylor

(based on the novel SIDEWAYS by Rex Pickett)

Starring: Paul Giamatti, Thomas Haden Church, Virginia Madsen & Sandra Oh

Alexander Payne has a very distinct style to his work. His films usually offer strong characters worth emotionally investing in and leave the viewer laughing or crying or both. There’s something about his serene sense of honest human emotion that manages to capture a realistic slice of life on the screen. That’s definitely the appeal for some people and may cause others to steer clear. I found myself split almost down the middle on my opinion of the hugely acclaimed, award-winning SIDEWAYS while watching it. By the time the credits began roll, I understood why this movie is so beloved. Aside from some minor pacing issues, SIDEWAYS is pretty much the perfect combination of heartfelt drama and charming comedy.


Miles Raymond is a deeply depressed writer struggling to get his first novel published. In addition to this character trait, Miles is also a huge fan of wine, a middle-school English teacher, recently divorced, and an alcoholic. Life might be looking up when he goes on a week-long trip through wine country with his soon-to-be-married best friend, Jack Cole. The two of them meet up with two fellow wine-loving women. Reluctant Miles finds himself falling for a waitress named Maya, while Jack is more than a little eager to cheat on his fiancé. Needless to say that both newfound relationships have their rocky points and the pair of friends wind up in hijinks aided by wine.


It should come as no surprise that characters are extremely important in a movie mainly centered around conversations and relationships. SIDEWAYS excels in bringing to life a group of people who feel too real for the screen. Thomas Haden Church plays the two-timing asshole Jack, but he’s not a one-dimensional scumbag. Jack seems to really care about Miles and tries his best to cheer him up throughout the film (albeit, most attempts backfire). Sandra Oh and Virginia Madsen are convincing as gals who could be on the lookout for love. The best performance comes in Paul Giamatti’s stellar Miles though. This is easily the most realistic portrayal of someone suffering from Depression that I’ve ever seen in any film. Miles may fly off the handles and cope with his problems in a damaging way (getting drunk seems to be his solution to everything), but he’s totally relatable to most people going through a severe rough patch in their lives. There’s something instantly likable about him, aided by some of the better comic relief moments throughout.


This may seem odd, but I think SIDEWAYS almost comes off as a more dramatic feature-length episode of SEINFIELD. That’s not mean to be a disparaging remark in the slightest. There isn’t really a story to be had. The plot is that these two friends go on a trip through wine country and meet some gals. There’s almost a quasi-sitcom like structure to be found within the film. It’s a film that’s technically about nothing, but winds up being emotionally about everything. The banter between Miles and Jack are mainly of the comedic variety, while Miles interactions with Maya lean heavily on the dramatic side of things. There are moments in SIDEWAYS where the film almost seems to lose focus, but then another scene or conversation comes along that snapped me right back into the film. The last 30 minutes or so of this movie are absolutely stellar containing the funniest scene of the entire film and an ending that hit my deepest emotions.


For a film that boils down to a group of friends tasting wine and talking with each other, SIDEWAYS packs a lot of emotion and humor. This is definitely a dramedy that starts off as a comedy, strikes a balance between the serious and funny scenes before ending on heartfelt drama. Paul Giamatti’s performance alone makes this film worth viewing. Add in witty dialogue, other smartly written characters (Thomas Haden Church is great as well), and a powerhouse final third, then you’ve got yourself a winner. SIDEWAYS does have a couple of small pacing issues, but there’s something so honest and touching about this film that I couldn’t help but love it! Like a fine wine, SIDEWAYS will only get better with age.

Grade: A

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