- Alexander Payne’s Sideways blends a poignant character study (really, it is three-headed character study) with perceptive comedy.
- Paul Giamatti plays Miles- and he is at the center of Payne’s (and writing partner Jim Taylor’s) sublime screenplay. Miles is (in his eyes at least) a failed writer and a failed husband. He is also a hilariously smug wine enthusiast “Quaffable, but far from transcendent” (haha!) and as his best friend Jack (a marvelous Thomas Haden Church) describes him “a negative guy”.
- Told in a largely invisible visual style by Payne.
- There are days of the week titles as we approach Jack’s upcoming wedding. This is a trip for Miles and Jack to wine country the week prior to the big day.
- Miles steals from his mother, and then catches the eye of himself in old photos on the dresser- potent melancholy. Payne deserves half the credit for casting Giamatti (who has never been better). Giamatti is coming off another all-time depressive in American Splendor (2003) and is the perfect fit for Miles.
- Virginia Madsen’s achievement is near equal to Giamatti’s and the three of them (including the energetic and jocular Haden Church) all really shine here. It is no fault of Sandra Oh that her Stephanie character is not quite as fleshed out as the other three.

Payne makes so many right choices that when he steers wrong—it is painful. The Rolfe Kent score (which has some nice pieces, like the theme for Madsen’s Maya) is, largely, a disaster. When it combines with a half-baked split-screen montage of wine country it feels like a parody almost. If Payne (and Kent) stick to Maya’s theme, and keep the rest of the score closer to that derivation (instead of trying to devise a wildly different theme for every mood) and stick to the patient dissolves (which Payne does well at times- give him credit) instead of seemingly hitting “random scene transition generator” (there are wipes thrown in for the fun of it) it is a markedly better film.
- Apparently for a period of time in 2004-2005 it actually helped spike Pinot sales and hurt Merlot sales.
- The scene where Miles and Jack are covered in blood (Jack) and spilled red wine (Miles) makes me laugh every time even after five viewings.
- In the film’s best scene (which is largely all acting and writing)- Miles describes himself when talking about his love of pinot. “thin skin, temperamental” and the need to be “coaxed out” to discover. This is genius. Madsen’s piano-soaked monologue after is just as strong.

At the 93-minute the best frame in the film is the shot of the two friends on the park bench looking- a superior cinematic painting
- Hayden Church is given a breakdown scene as well- the scene where he is talking about his missing rings.

The location scouting for Maya’s (Madsen) apartment deserves praise– her cute little corner apartment up the stairs will serve as the location for the conclusion of the film—the voicemail (where we hear her music theme again) and Payne shows Miles knocking on the door- brilliant.
- There are many lovely and painful truths in Sideways—though they capture characters at different ages—it feels like Lady Bird is a film worth comparing it to.
- Recommend but ultimately not in the top 10 of 2004—perhaps enough to push to the R/HR border
Damn, I’m sure this one hurt a little. If I remember correctly you had this as a MS in the past but you’ll probably tell me in a second I’m confusing it with some other Payne film.
Not sure about it’s history on the site, but MS is indeed in line with my recollections of Drake’s position on this film. This is a bit of a shock.
Yes on Payne’s page it is a MS and listed at #72 of the 2000’s. It is one of my favourite films right now so disappointed to see it drop so heavily.
@Harry and Matt – It is also Payne’s only film in the TSPDT Top 1000, at #780, as well as #66 on the 21st Century List.
@Matt @Zane and @Harry- yes, I’d like to think I’m making the site a little better each day but as I’ve said before I’m sure for every two steps forward I take one back. There is always the chance I am wrong on a film of course. I still think highly of Sideways, but it is all relative. The gulf between say 2046 (another former MS-ranked film from 2004 that I had the chance to revisit) and Sideways is… well… quite a gulf.
@Drake – Hmm…
>2046
>No longer a MS
>Much higher than a R
It’s all coming together…
If you can give a reasonable estimate, when do you think the As Tears Go By and 2046 pages will come out?
@Zane- October 9th and October 11th
“Apparently, George Clooney had early interest in the role, and thank God Payne cast Giamatti instead (no offense to the great Clooney but it’s the wrong fit).”
Clooney actually wanted Haden Church’s role, not Giamatti’s.
@Harry- thanks for the cleanup here. That makes more sense.
@Malith- thanks. This has been fixed