Paul Giamatti as Miles Raymond
Thomas Haden Church as Jack
Virginia Madsen as Maya
Sandra Oh as Stephanie
Marylouise Burke as Phyllis
Missy Doty as Cammie
M.C. Gainey as Cammie’s husband
Patrick Gallagher as Gary the Bartender
Alex Kalognomos as Alex Erganian
Joe Marinelli as Pourer
Alysia Reiner as Christine

Hilarious breakout performances by Paul Giamatti and Thomas Haden Church make Sideways Alexander Payne’s funniest film so far, but as always, the filmmaker’s keen eye for human nature and behavior makes it equally poignant.

Miles and Jack (Giamatti and Church) are college buddies, who take a weeklong tour of California wine country to celebrate Jack’s impending marriage. Miles is a writer and a wine lover, trying to recover emotionally from a painful divorce, while Jack is a third-rate actor using the trip to get a bit of action before he has to commit himself to one woman. Along the way, they meet Maya and Stephanie (Virginia Madsen and Sandra Oh), two women who have a deep impact on their plans and on their lives.

For his fourth movie, filmmaker Alexander Payne and writing partner Jim Taylor have adapted Rex Pickett’s semi-fictitious book that transplants the typical buddy road comedy into the classier setting of wine tasting. Unlike their last movie, About Schmidt, which looked at aging and retirement, Sideways‘ protagonists are in their late 30’s and early 40’s, allowing them to explore another side of the human experience.

The movie’s title represents the lateral movement of Miles and Jack’s lives, and though Jack’s upcoming marriage may change that, Miles has gotten so used to his lackadaisical lifestyle teaching 8th grade English rather than writing. Even the one novel he did write, an enormous unreadable tome, has been turned down by most publishers, and there’s very little that can get him out of his cycle of drinking and depression. Both guys have gotten very good at avoiding the reality of their pathetic lives by putting on facades to everyone they meet, including each other.

The duo’s road trip starts innocently enough with visits to a number of wineries as Miles tries to teach his less cultured pal Jack about wine, but Jack is more interested in hooking up with Stephanie, a single mother that gets Jack rethinking his upcoming marriage. Jack’s not all bad though, as he does give Miles the opportunity to spend time with Maya (Madsen), a local waitress who shares his love for wine. Things go “sideways” when Stephanie and Maya find out that Jack is getting married. It’s a fairly simple premise with a cast of just four characters, but that’s all that is needed for Payne to create a rich story.

Paul Giamatti’s Miles is a particularly colorful character on a par with his take on Harvey Pekar in last year’s American Splendor. It allows Giamatti to show off his usual comic timing, but lacing it with a certain pathos that viewers will be able to sympathize or even empathize with. It’s this ability to play a very realistic everyman that makes Giamatti such an amazing actor, even if he is once again playing a rather odd character. Thomas Haden Church, whose claim to fame came from roles on sitcoms like “Wings” and “Ned and Stacy”, gives a totally over-the-top performance as a guy who is always “on”. When he breaks down later in the movie, you’re not sure whether he’s acting to try to manipulate Miles into doing something for him or if he’s really been destroyed by the thought of losing his fiancĂ©.

The actors are better matched than their characters, playing off each other as well as the original Odd Couple, and it often only takes a face or reaction to one another that brings on great laughs. Almost every aspect of being a man and dealing with women and relationships-both good and bad-is covered between them, but that doesn’t necessarily make Sideways a “guy’s movie,” since there’s a good deal of romance and humanity that should appeal equally to both genders.
This becomes clear when the movie’s turning point is a quiet moment between Miles and Maya sitting on a porch talking about wine. This scene gives the lovely Virginia Madsen the chance to deliver a soliloquy that will have every man in the audience eating out of the palm of her hand. It’s a key scene that defines their relationship for the rest of the movie, making you want to yell out “Kiss her, you idiot!”

Beyond the onscreen interplay between the four actors, the movie’s most entertaining moments are those that are the most genuine, such as a side trip to visit Miles’ mom. It’s this realistic interaction between people that Payne is so good at and really nails it in this movie. In the midst of all the humor and drama, he also creates a beautiful travelogue of California wine country with montages scored by Rolfe Kent with light upbeat jazz, and it’s a fun way to learn more about wine. The only real problem is that the movie is a bit long at two hours, although it never really gets boring.

The Bottom Line:
Alexander Payne has done it again, making a comedy that rings so true to real life that most people in a certain age bracket should be able to relate with some aspect of the characters. Rich with humor and romance, Sideways also shows a continued maturity in Payne as a filmmaker. It’s a very special film and one of the year’s best.

Sideways opens in New York and Los Angeles on Friday and elsewhere over the course of October and November.