8 Best Movies of 1999

By Vlad Zakh · June 30, 2026

1999 was a landmark year. Toy Story 2 has toys rescuing a kidnapped cowboy, Magnolia interweaves strangers’ lives in the San Fernando Valley, and The Sixth Sense has a psychologist helping a boy who sees the dead. The Iron Giant, American Beauty, The Matrix, Fight Club and The Green Mile round out the eight.

Toy Story 2 (1999)

TMDB ★ 7.6

A vintage toy collector kidnaps a cowboy doll, prompting his friends to mount a daring rescue.

Directed by John Lasseter · 1h 32m · Rated G

Where to watch

Stream: Disney Plus, Hulu · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Magnolia (1999)

IMDb ★ 8.0 RT 82% Metacritic 78

Sprawling, strange, and one of the most ambitious ensemble dramas of the decade.

Directed by Paul Thomas Anderson · 3h 09m · Rated R

Nominated for 3 Oscars28 wins & 59 nominations

Where to watch

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

▶ Trailer Letterboxd

The Sixth Sense (1999)

IMDb ★ 8.2 RT 86% Metacritic 64

A troubled child psychologist tries to help a young boy who claims he can see dead people.

Directed by M. Night Shyamalan · 1h 47m · Rated PG-13

Nominated for 6 Oscars37 wins & 56 nominations

Where to watch

Stream: Netflix, Apple TV, Hulu, fuboTV, YouTube TV, Netflix Standard with Ads · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

The Iron Giant (1999)

IMDb ★ 8.1 RT 96% Metacritic 85

A young boy befriends a giant alien robot and has to protect it from a paranoid government agent.

Directed by Brad Bird · 1h 26m · Rated PG

Won 1 BAFTA Award20 wins & 18 nominations

Where to watch

Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Spectrum On Demand · 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

The Matrix (1999)

IMDb ★ 8.7 RT 83% Metacritic 73

A hacker discovers reality is a simulation built to keep humanity docile.

Directed by Lana Wachowski & Lilly Wachowski · 2h 16m · Rated R

Won 4 Oscars42 wins & 52 nominations

Where to watch

Stream: YouTube TV, VIX · Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Spectrum On Demand · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Fight Club (1999)

IMDb ★ 8.8 RT 81% Metacritic 67

A satire so stylish that a lot of viewers missed it was a satire at all.

Directed by David Fincher · 2h 19m · Rated R

Nominated for 1 Oscar12 wins & 38 nominations

Where to watch

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

▶ Trailer Letterboxd

The Green Mile (1999)

IMDb ★ 8.6 RT 78% Metacritic 61

A death row prison guard witnesses miraculous events around a gentle inmate convicted of a brutal crime.

Directed by Frank Darabont · 3h 09m · Rated R

Nominated for 4 Oscars15 wins & 37 nominations

Where to watch

Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Spectrum On Demand · 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.

8 Best Movies of 1999

Toy Story 2 (1999)

Magnolia (1999)

The Sixth Sense (1999)

The Iron Giant (1999)

American Beauty (1999)

The Matrix (1999)

Fight Club (1999)

The Green Mile (1999)

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