Sideways

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🎙️ EPISODE 603: 11.22.22 This is probably Alexander Payne's best movie. It's certainly his most beloved. I'm torn on whether or not I should put it atop the list and bestow it with a perfect 10 grade, though. I think my main issue on this most recent rewatch was the simple (and unavoidable) fact I've seen it too many times? I felt this way going through some of the Paul Thomas Anderson classics earlier this year. There does seem to be a max-out point for even the best films ever made. I can't really put my finger on it. I find myself having to almost remove my personal experience/relationship to the picture completely. However, in Payne's case, it had been interesting viewing his work in chronological order. There's a wonderful bit of connective tissue running through these first four Alexander Payne films.

Aside from the obvious dissections of various American ideals, each one seems to feature an increasingly loathsome figure at the center. Where it's easy to feel bad for and connect with some like Citizen Ruth, the plight of Miles in Sideways is far harder to actually empathize with even if it's probably more tangible for the average member of the target audience. The character of Jack (Thomas Haden Church) is kind of a parlor trick. He's so overtly 'bad' that it almost overshadows what a vile loser his pathetic pal is. All of this is anchored by the truly great performances, and the actual trick of the movie is Paul Giamatti making us feel sympathy for Miles in the end.

Also, the tonal shift from black comedies to the world of the dramedy is complete now, no looking back. While there are still plenty of laughs, this is a Serious Movie, void of an even an ounce of satire. To that end, it registers more gravitas and sincerity right at the onset, almost by definition. In and of itself, this is neither bad nor good, but it does signal (perhaps) that Payne wants to be taken more seriously. And he has the receipts to prove it.

CHRONOLOGICALLY
⫷ EPISODE 602 - (YOU ARE HERE) - EPISODE 604 ⫸

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Sideways is a 2004 American comedy-drama road film directed by Alexander Payne and written by Jim Taylor and Payne. A film adaptation of Rex Pickett's 2004 novel of the same name, Sideways follows two men in their forties, Miles Raymond (Paul Giamatti), a depressed teacher and unsuccessful writer, and Jack Cole (Thomas Haden Church), a past-his-prime actor, who take a week-long road trip to Santa Barbara County wine country to celebrate Jack's upcoming wedding. Sandra Oh and Virginia Madsen also star as women they encounter during their trip. The film premiered at the Toronto International Film Festival. Sideways received widespread acclaim from critics and regarded as one of the greatest films of the 2000s. It was nominated for Best Picture, Best Director, Best Supporting Actor (Haden Church) and Best Supporting Actress (Madsen), winning Best Adapted Screenplay at the 77th Academy Awards. It was released on September 13, 2004.