Movies Like Tootsie
If you loved Tootsie's Comedy and Romance storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.
★ Top Picks

Romance & Cigarettes
Ironworker 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. Kitty kicks Nick out of the house, and he is forced to make some difficult decisions.

Carnal Knowledge
Two lifelong friends navigate complex sexual encounters and emotional entanglements, wrestling with societal norms and personal desires.

Someone Great
An 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 outrageous last adventure in New York City.

Not Okay
An ambitious young woman, desperate for followers and fame, fakes a trip to Paris to up her social media presence. When a terrifying incident takes place in the real world and becomes part of her imaginary trip, her white lie becomes a moral quandary that offers her all the attention she’s wanted.

Down with Love
In 1962 New York City, love blossoms between a playboy journalist and a feminist advice author.

Last Night
Michael and Joanna are a young and successful married couple who appear to have it all. But when Michael finds himself alone on a business trip with an attractive new colleague and Joanna encounters the other great love of her life, each is thrust into an evening of temptation.

Manhattan
Manhattan explores how the life of a middle-aged television writer dating a teenage girl is further complicated when he falls in love with his best friend's mistress.

Little Manhattan
Ten-year-old Gabe Burton is just an average kid growing up in Manhattan until Rosemary Telesco walks into his karate class. But before Gabe can tell Rosemary how he feels, she reveals that she won't be going to public school any more. Gabe has a lot more to learn about life, love, and girls.
More Movies Like Tootsie

How to Be Single
New 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 of love.

Sex and the City
A New York writer on sex and love is finally getting married to her Mr. Big. But her three best girlfriends must console her after one of them inadvertently leads Mr. Big to jilt her.

Someone Like You...
Jane 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 begins an extensive study of the male animal, including her womanizing roommate Eddie. Jane puts her studies and romantic misadventure to use as a pseudonymous sex columnist -- and becomes a sensation.

Alfie
A tale of a philosophical womanizer who is forced to question his seemingly carefree existence.

Hello, My Name Is Doris
A self-help seminar inspires a sixty-something woman to romantically pursue her younger co-worker.

Unfaithful
A New York suburban couple's marriage goes dangerously awry when the wife indulges in an adulterous fling.

Ricky Stanicky
When 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 immature behavior. But when their spouses and partners get suspicious and demand to finally meet the fabled Mr. Stanicky, the guilty trio decide to hire a washed-up actor and raunchy celebrity impersonator to bring him to life.

Trust
Set in the glamour of the New York and Paris art scenes, gallery owner Brooke Gatwick and her newscaster husband Owen Shore, face temptation, jealousy, twists and mystery when two seductive newcomers enter their lives.

Breakfast at Tiffany's
Holly Golightly is an eccentric New York City playgirl determined to marry a Brazilian millionaire. But when young writer Paul Varjak moves into her apartment building, her past threatens to get in their way.

Friends with Benefits
Dylan 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 without any emotional attachment.

Heights
Spanning twenty-four hours, HEIGHTS follows five New Yorkers challenged to choose their destiny before the sun comes up the next day.

Sleeping with Other People
Can 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 monogamy-challenged ways, neither can maintain a relationship. Determined to stay friends despite their mutual attraction, they make a pact to keep it platonic, a deal that proves easier said than done.
Why These Movies Are Similar
These recommendations share core qualities with Tootsie (1982): Comedy and Romance themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of Tootsie.
See full details for Tootsie (1982)