Sideways

2004 Alexander Payne 2h 7m ★ 7.1
Comedy Drama Romance
Sideways

Two middle-aged men embark on a spiritual journey through Californian wine country. One is an unpublished novelist suffering from depression, and the other is only days away from walking down the aisle.

Cast

Paul Giamatti Paul Giamatti Miles
Thomas Haden Church Thomas Haden Church Jack
Virginia Madsen Virginia Madsen Maya
Sandra Oh Sandra Oh Stephanie
Marylouise Burke Marylouise Burke Miles's Mother
Jessica Hecht Jessica Hecht Victoria
Missy Doty Missy Doty Cammi
M.C. Gainey M.C. Gainey Cammi's Husband

Double Feature Pairings

Films that pair perfectly with Sideways

Withnail & I
Withnail & I 1987
Two drinking holidays that are really about failure, friendship, and the lies men tell themselves. Another Round
Another Round 2020
Midlife through alcohol. Two films about men who drink to feel alive and discover it might be killing them.