29 Best Movies Like Tootsie ...

2h 5m Comedy Drama Family

Loving but irresponsible dad Daniel Hillard, estranged from his exasperated spouse, is crushed by a court order allowing only weekly visits with his kids. When Daniel learns his ex needs a housekeeper, he gets the job -- disguised as an English nanny. Soon he becomes not only his children's best pal but the kind of parent he should have been from the start.

1h 42m Comedy Drama Romance

No sooner does Italian-American widow Loretta accept a marriage proposal from her doltish boyfriend, Johnny, than she finds herself falling for his younger brother, Ronny. She tries to resist, but Ronny lost his hand in an accident he blames on his brother, and has no scruples about aggressively pursuing her while Johnny is out of the country. As Loretta falls deeper in love, she comes to learn that she's not the only one in her family with a secret romance.

2h 14m Drama Comedy Romance

Shakespeare's comedy of gender confusion, in which a girl disguises herself as a man to be near the count she adores, only to be pursued by the woman he loves.

1h 51m Comedy Romance

Paula knows that, in romance, all actors follow the same stage instruction: Exit. Without warning, her actor boyfriend splits for a movie role, and sublets their Manhattan apartment to Elliot, another actor.

1h 41m Comedy Drama Romance

It's New York City in 1981, and various twentysomethings are converging on a New Year's Eve party.

1h 54m Comedy Romance

Tess McGill is an ambitious secretary with a unique approach for climbing the ladder to success. When her classy, but villainous boss breaks a leg skiing, Tess takes over her office, her apartment and even her wardrobe. She creates a deal with a handsome investment banker that will either take her to the top, or finish her off for good.

2h 4m Romance Comedy Drama

William Thacker is a London bookstore owner whose humdrum existence is thrown into romantic turmoil when famous American actress Anna Scott appears in his shop. A chance encounter over spilled orange juice leads to a kiss that blossoms into a full-blown affair. As the average bloke and glamorous movie star draw closer and closer together, they struggle to reconcile their radically different lifestyles in the name of love.

1h 48m Comedy Romance

Melanie Parker, an architect and mother of Sammy, and Jack Taylor, a newspaper columnist and father of Maggie, are both divorced. They meet one morning when overwhelmed Jack is left unexpectedly with Maggie and forgets that Melanie was to take her to school. As a result, both children miss their school field trip and are stuck with the parents. The two adults project their negative stereotypes of ex-spouses on each other, but end up needing to rely on each other to watch the children as each must save his job. Humor is added by Sammy's propensity for lodging objects in his nose and Maggie's tendency to wander.

1h 36m Comedy Romance Drama

During their travel from Chicago to New York, Harry and Sally debate whether or not sex ruins a friendship between a man and a woman. Eleven years later, and they're still no closer to finding the answer.

1h 43m Comedy Romance

Distraught when her middle-aged lover breaks a date with her, 21-year-old Toni Simmons attempts suicide. Impressed by her action, her lover, dentist Julian Winston reconsiders marrying Toni, but he worries about her insistence on honesty. Having fabricated a wife and three children, Julian readily accepts when his devoted nurse, Stephanie, who has secretly loved Julian for years, offers to act as his wife and demand a divorce.

1h 52m Comedy Drama Romance

Though Rachel is a successful attorney and a loyal, generous friend, she is still single. After one drink too many at her 30th-birthday celebration, Rachel unexpectedly falls into bed with her longtime crush, Dex -- who happens to be engaged to her best friend, Darcy. Ramifications of the liaison threaten to destroy the women's lifelong friendship, while Ethan, Rachel's confidant, harbors a potentially explosive secret of his own.

1h 27m Comedy Drama Romance

The Four Faced Liar is a story of love and lies for four twenty-somethings looking to find themselves in New York City... A story of love and lies for four twenty-somethings looking to find themselves in New York City. A pair of best friends and a seemingly perfect couple meet at a local Irish pub tucked in the winding streets of the West Village. Through their chance meeting, the four bond and over time all of their relationships with one another morph into love, betrayal and heartbreak for all.

2h 1m Drama

Eleven articulate people work through affairs of the heart in L.A. Paul produces Hannah's TV cooking show. Mark is dying of AIDS. Men have scalded Meredith so she rebuffs Trent's charm, but he persists. The trendy, prolix Joan tries to pull the solitary Keenan into her orbit. An adulterous couple meet at hotels for evening sex. Hugh tells tall tales, usually tragic, to women in bars.

1h 33m Comedy Romance

A successful veterinarian and radio show host with low self-esteem asks her model friend to impersonate her when a handsome man wants to see her.

1h 29m Drama Romance Comedy

A woman who is robbed on her way to catch the 1:30 train to Boston is left stranded in New York City. She meets a man who helps her during the course of the night and the two form a romance.

1h 45m Comedy Romance

A young advertising executive's life becomes increasingly complicated when, in order to impress her boss, she pretends to be engaged to a man she has just met.

1h 58m Drama Romance Comedy

When Johnny is released from prison following a forgery charge, he quickly lands a job as a short-order cook at a New York diner. Following a brief fling with waitress Cora, Frankie develops an attraction for Cora's friend and fellow waitress Frankie. While Frankie resists Johnny's charms initially, she eventually relents when her best friend, Tim, persuades her to give Johnny a chance.

1h 43m Comedy Drama Romance

Overachieving actress Rebecca must come to grips with her failing marriage to stay-at-home dad Tom. While Rebecca's slacker brother Tobey can't seem to commit to his aspiring-novelist girlfriend, Elaine. As both relationships spin out of control, the two couples embark on a quest to rediscover the magic and romance of falling in love in New York.

1h 48m Comedy Drama Romance

Cousin Bette is a poor and lonely seamstress, who, after the death of her prominent and wealthy sister, tries to ingratiate herself into lives of her brother-in-law, Baron Hulot, and her niece, Hortense Hulot. Failing to do so, she instead finds solace and company in a handsome young sculptor she saves from starvation. But the aspiring artist soon finds love in the arms of another woman, Hortense, leaving Bette a bitter spinster. Bette plots to take revenge on the family who turned her away and stole her only love. With the help of famed courtesan Jenny Cadine she slowly destroys the lives of those who have scorned her.

2h 1m Comedy Drama Romance

After being cut from the USA softball team and feeling a bit past her prime, Lisa finds herself evaluating her life and in the middle of a love triangle, as a corporate guy in crisis competes with her current, baseball-playing beau.

1h 43m Comedy Drama Romance

The misadventures of four groups of guests at the Beverly Hills Hotel.

1h 50m Comedy Drama Romance

The life of super-yuppie J.C. is thrown into turmoil when she inherits a baby from a distant relative.

2h 7m Comedy Romance

An ugly duckling having undergone a remarkable change, still harbors feelings for her crush: a carefree playboy, but not before his business-focused brother has something to say about it.