Movies like Tootsie

Just One of the Guys

1985

cross dressing · Romance, Comedy · Columbia Pictures

You Can't Take It with You

1938

love, friends · Romance, Comedy · Columbia Pictures

Sabrina

1995

Also Sydney Pollack · Romance, Comedy · Mirage Enterprises

Friends with Benefits

2011

new york city, love, friends · Romance, Comedy

Mr. Deeds Goes to Town

1936

new york city · Romance, Comedy · Columbia Pictures

100 Girls

2000

feminist, cross dressing · Romance, Comedy

Down with Love

2003

new york city, feminist · Romance, Comedy

Electric Dreams

1984

Close on feel, same era · Romance, Comedy

50 First Dates

2004

love · Romance, Comedy · Columbia Pictures

She's Funny That Way

2015

infidelity, new york city · Romance, Comedy

Everyone Says I Love You

1996

new york city, infidelity · Romance, Comedy

Green Card

1990

love · Romance, Comedy

Roxanne

1987

Romance, Comedy · Columbia Pictures

The Awful Truth

1937

Romance, Comedy · Columbia Pictures

Time Freak

2018

love · Romance, Comedy

Something's Gotta Give

2003

new york city · Romance, Comedy · Columbia Pictures

Barefoot in the Park

1967

new york city, love · Romance, Comedy

Working Girl

1988

new york city · Romance, Comedy

Multiplicity

1996

Romance, Comedy · Columbia Pictures

Isn't It Romantic

2019

new york city · Romance, Comedy

I Love You Phillip Morris

2010

witty · Romance, Comedy

Paris When It Sizzles

1964

witty · Romance, Comedy

Coming to America

1988

new york city · Romance, Comedy

Real Genius

1985

Close on feel, same era · Romance, Comedy