6 Best Cross-Dressing Disguise Comedy Movies

By Vlad Zakh · June 26, 2026

Slipping into a disguise as the opposite sex has been a comedy staple for decades, mostly because it lets characters see the world from somewhere new. Mrs. Doubtfire has a divorced dad posing as an elderly nanny, White Chicks sends two disgraced FBI agents undercover as socialite sisters, and Yentl has a young woman disguising herself to study. Victor/Victoria, Tootsie and Some Like It Hot round out the six.

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 father disguises himself as an elderly nanny just to stay close to his own kids.

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 woman disguises herself as a man to study the Torah in a world that forbids it to her.

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

An unemployable actor lands his biggest role yet by disguising himself as a woman.

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 after witnessing a gangland killing.

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. 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 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