6 Best Oscar Best Actress Winners of the 1990s

By Vlad Zakh · June 19, 2026

The 1990s Best Actress winners were fierce and unforgettable. Hilary Swank won for Boys Don’t Cry, Gwyneth Paltrow for Shakespeare in Love, Frances McDormand for Fargo and Susan Sarandon for Dead Man Walking. Jessica Lange in Blue Sky and Emma Thompson in Howards End round out the six.

Boys Don't Cry (1999)

IMDb ★ 7.5 RT 90% Metacritic 86

A trans man's new life and relationships in a small Nebraska town end in real, brutal violence.

Directed by Kimberly Peirce · 1h 58m · Rated R

Won 1 Oscar50 wins & 39 nominations

Where to watch

Rent or buy: Amazon Video, Apple TV Store, Fandango At Home

▶ Trailer Letterboxd

Shakespeare in Love (1998)

TMDB ★ 7.1

A struggling playwright finds inspiration and forbidden romance while staging Romeo and Juliet.

Directed by John Madden · 2h 04m · Rated R

Where to watch

Stream: fuboTV, Paramount Plus Premium, Paramount Plus Essential, Paramount+ Amazon Channel, Paramount+ Roku Premium Channel · 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

Fargo (1996)

IMDb ★ 8.1 RT 95% Metacritic 88

A car salesman's botched kidnapping scheme spirals into a series of increasingly violent complications.

Directed by Joel Coen · 1h 38m · Rated R

Won 2 Oscars84 wins & 59 nominations

Where to watch

Stream: Hulu, fuboTV, MGM+ Amazon Channel, Philo, MGM Plus Roku Premium Channel, MGM Plus · Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Plex · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

▶ Trailer Letterboxd

Dead Man Walking (1995)

TMDB ★ 7.5

A nun becomes the spiritual adviser to a convicted murderer awaiting execution on death row.

Directed by Tim Robbins · 2h 02m · Rated R

Where to watch

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

▶ Trailer Letterboxd

Blue Sky (1994)

TMDB ★ 6.4

A military wife's erratic, free-spirited behaviour threatens her husband's career and their marriage during the Cold War.

Directed by Tony Richardson · 1h 41m · Rated PG-13

Where to watch

Stream: fuboTV, MGM+ Amazon Channel, Philo, MGM Plus Roku Premium Channel, MGM Plus · Rent or buy: Fandango At Home

▶ Trailer Letterboxd

Howards End (1992)

TMDB ★ 7.4

The fates of three families from different social classes become entangled around the inheritance of a country house.

Directed by James Ivory · 2h 22m · Rated PG

Where to watch

Stream: Cohen Media Amazon Channel · Rent or 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 Oscar Best Actress Winners of the 1990s

Boys Don't Cry (1999)

Shakespeare in Love (1998)

Fargo (1996)

Dead Man Walking (1995)

Blue Sky (1994)

Howards End (1992)

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