6 Best Midlife Crisis Movies of All Time

By Vlad Zakh · March 14, 2026

Middle-aged regret and reinvention are very good comic and dramatic material. This Is 40 has a couple facing money trouble and ageing parents, Up in the Air has a rootless consultant challenged by romance, and About Schmidt has a retired widower questioning everything on a road trip. Sideways, American Beauty and City Slickers round out the six.

This Is 40 (2012)

TMDB ★ 5.9

A couple approaching forty confronts financial strain, ageing parents and marital frustration.

Directed by Judd Apatow · 2h 14m · Rated R

Where to watch

Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Up in the Air (2009)

TMDB ★ 7.4

A corporate downsizer who lives entirely out of a suitcase is forced to confront how empty that life really is.

Directed by Jason Reitman · 1h 50m · Rated R

Where to watch

Stream: fuboTV, Paramount Plus Premium, Paramount Plus Essential, Paramount+ Amazon Channel, Paramount+ Roku Premium Channel · Rent: JustWatch TV, Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Sideways (2004)

IMDb ★ 7.5 RT 97% Metacritic 94

Two friends' wine-country trip before one's wedding turns into a real reckoning with failure.

Directed by Alexander Payne · 2h 07m · Rated R

Won 1 Oscar123 wins & 91 nominations

Where to watch

Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

About Schmidt (2002)

TMDB ★ 7.2

A newly retired, widowed insurance actuary questions the meaning of his life on a road trip.

Directed by Alexander Payne · 2h 05m · Rated R

Where to watch

Stream: The Roku Channel, Howdy Amazon Channel · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

American Beauty (1999)

IMDb ★ 8.3 RT 87% Metacritic 84

A suburban father's midlife crisis upends his family when he becomes infatuated with his daughter's friend.

Directed by Sam Mendes · 2h 02m · Rated R

Won 5 Oscars112 wins & 102 nominations

Where to watch

Rent: JustWatch TV, Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

City Slickers (1991)

TMDB ★ 6.8

Three stressed city friends sign up for a cattle-drive holiday that becomes an unexpected life lesson.

Directed by Ron Underwood · 1h 54m · Rated PG-13

Where to watch

Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Streaming availability data from JustWatch, via TMDB. Availability changes often, so check the service before you plan a movie night.

Vlad Zakh

Founder, Movieix

Founder of Movieix. He started the site because most recommendation pages felt like noise. Here, lists are sorted by who's in the film, where it's from and what mood you're in tonight.

6 Best Midlife Crisis Movies of All Time

This Is 40 (2012)

Up in the Air (2009)

Sideways (2004)

About Schmidt (2002)

American Beauty (1999)

City Slickers (1991)

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