Movies Like Tootsie
If you liked Tootsie (1982), a comedy and romance movie directed by Sydney Pollack, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.
- 1
Romance & Cigarettes (2006)
★ 6/10Also comedy and romanceIronworker Nick lives with his wife, Kitty, and three daughters. When he meets a significantly younger woman, Tula, he starts an affair with her, much to the chagrin of his wife, and his life is thrown into upheaval…
- 2
Someone Great (2019)
★ 6.4/10Also comedy and romanceAn aspiring music journalist lands her dream job and is about to move to San Francisco when her boyfriend of nine years decides to call it quits. To nurse her broken heart, she and her two best friends spend one…
- 3
Down with Love (2003)
★ 6.1/10Also comedy and romanceIn 1962 New York City, love blossoms between a playboy journalist and a feminist advice author.
- 4
Someone Like You... (2001)
★ 6/10Also comedy and romanceJane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane…
- 5
How to Be Single (2016)
★ 6.3/10Also comedy and romanceNew York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions…
- 6
One Night Only (2026)
★ 6.4/10Also romance and comedyTwo love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.
- 7
Ricky Stanicky (2024)
★ 6.5/10Also comedyWhen three childhood best friends pull a prank gone wrong, they invent the imaginary Ricky Stanicky to get them out of trouble. Twenty years later, the trio still uses the nonexistent Ricky as a handy alibi for their…
- 8
Sleeping with Other People (2015)
★ 6.3/10Also comedy and romanceCan two serial cheaters get a second chance at love? After a one-night stand in college, New Yorkers Lainey and Jake meet by chance twelve years later and discover they each have the same problem: because of their…
- 9
The Lonely Guy (1984)
★ 6.2/10Also comedy and romanceA writer for a greeting card company learns the true meaning of loneliness when he comes home to find his girlfriend in bed with another man.
- 10
Friends with Benefits (2011)
★ 6.6/10Also romance and comedyDylan is done with relationships. Jamie decides to stop buying into the Hollywood clichés of true love. When the two become friends they decide to try something new and take advantage of their mutual attraction - but…
- 11
My Sassy Girl (2008)
★ 6.8/10Also comedy and romanceA guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
- 12
No Hard Feelings (2023)
★ 6.7/10Also comedy and romanceOn the brink of losing her childhood home, Maddie discovers an intriguing job listing: wealthy helicopter parents looking for someone to “date” their introverted 19-year-old son, Percy, before he leaves for college. To…
- 13
¿Quieres ser mi hijo? (2023)
★ 8.4/10Also comedy and romanceLu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
- 14
Focus (2015)
★ 6.9/10Also romance and comedyNicky, an accomplished con artist, gets romantically involved with his disciple Jess but later ends their relationship. Years later, she returns as a femme fatale to spoil his plans.
- 15
Players (2024)
★ 6.1/10Also romance and comedyNew York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing…
- 16
That Awkward Moment (2014)
★ 6.1/10Also comedy and romanceBest pals Jason and Daniel indulge in casual flings and revel in their carefree, unattached lives. After learning that the marriage of their friend Mikey is over, they gladly welcome him back into their circle. The…
- 17
Broadcast News (1987)
★ 6.8/10Also comedy and romanceA high-strung news producer finds herself in a love triangle between a talented but self-doubting reporter and a charming news anchor who embodies the growing trivialization of news that she is determined to fight…
- 18
Just One of the Guys (1985)
★ 6.4/10Also comedy and romanceWhen Terry Griffith loses her high school's writing competition, she's convinced that it's because she's a girl. So Terry decides to change high schools and pose as a boy to prove her point. Her brother, Buddy, helps…
- 19
What's New Pussycat? (1965)
★ 5.9/10Also comedy and romanceA playboy who refuses to give up his hedonistic lifestyle to settle down and marry his true love seeks help from a demented psychoanalyst who is having romantic problems of his own.
- 20
How to Date Billy Walsh (2024)
★ 6.4/10Also romance and comedyArchie has been in love with his best friend Amelia for as long as he can remember. Just when he builds up the courage to declare his feelings, she falls head over heels for Billy Walsh, a new American transfer student.