Sideways (2004)

Name: Sideways
Released: 2004

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 One is an unpublished novelist suffering from depression, and the other is only days away from walking down the aisle.

Genres: Comedy, Drama, Romance

What to watch after Sideways

Inside Llewyn Davis (2013) — Same feel: realistic, melancholy
The Holdovers (2023) — Same feel: melancholy, reflective
About Schmidt (2002) — Alexander Payne directed both
Once Upon a Time... in Hollywood (2019) — Same subject: buddy
In Search of a Midnight Kiss (2007) — Same feel: realistic, reflective
Another Year (2010) — Same feel: realistic, melancholy