6 Best Cross-Dressing Disguise Comedy Movies

By Vlad Zakh · June 26, 2026

Slipping into a disguise of the opposite gender has powered some of comedy’s most enduring premises, forcing characters to see the world from an entirely new vantage point. In Some Like It Hot (1959): Two musicians disguise themselves as women to escape the mob, complicating their romantic pursuits. Just as strong is Tootsie (1982): A struggling actor disguises himself as a woman to land a role, only to fall for his own co-star.

White Chicks (2004)

TMDB ★ 5.7

Two disgraced FBI agents go undercover disguised as wealthy socialite sisters to crack a kidnapping case.

Directed by Keenen Ivory Wayans · 1h 49m · Rated PG-13

Where to watch

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

▶ Trailer Letterboxd

Mrs. Doubtfire (1993)

IMDb ★ 7.1 RT 71% Metacritic 54

A recently divorced father disguises himself as an elderly nanny to stay close to his children.

Directed by Chris Columbus · 2h 05m · Rated PG-13

Won 1 Oscar11 wins & 10 nominations

Where to watch

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

▶ Trailer Letterboxd

Yentl (1983)

IMDb ★ 6.6 RT 69% Metacritic 68

A young woman disguises herself as a man to pursue forbidden religious education in early 1900s Poland.

Directed by Barbra Streisand · 2h 12m · Rated PG

Won 1 Oscar6 wins & 17 nominations

Where to watch

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

▶ Trailer Letterboxd

Victor/Victoria (1982)

TMDB ★ 7.3

A struggling singer poses as a female impersonator to find success in 1930s Parisian nightlife.

Directed by Blake Edwards · 2h 14m · Rated PG

Where to watch

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

▶ Trailer Letterboxd

Tootsie (1982)

TMDB ★ 7.6

A struggling actor disguises himself as a woman to land a role, only to fall for his own co-star.

Directed by Sydney Pollack · 1h 56m · Rated PG

Where to watch

Stream: Sony Pictures Core Amazon 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

Some Like It Hot (1959)

IMDb ★ 8.2 RT 95% Metacritic 98

Two musicians disguise themselves as women to escape the mob, complicating their romantic pursuits.

Directed by Billy Wilder · 2h 03m

Won 1 Oscar11 wins & 13 nominations

Where to watch

Stream: fuboTV, MGM+ Amazon Channel, Philo, MGM Plus Roku Premium Channel, YouTube TV, MGM Plus · 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, built to fix a specific annoyance: most recommendation sites are just algorithm-driven noise. Our lists are researched and organized by who's in a film, where it's from, and the mood you're actually in tonight.

6 Best Cross-Dressing Disguise Comedy Movies

White Chicks (2004)

Mrs. Doubtfire (1993)

Yentl (1983)

Victor/Victoria (1982)

Tootsie (1982)

Some Like It Hot (1959)

You might also like

6 Best Nanny and Childcare Movies

6 Best Golden Globe Best Actor Musical or Comedy Winning Movies

50 Best Comedy Movies of All Time

Best 20 American Comedy Movies

15 Best 90s Comedy Movies

7 Best Billy Wilder Movies