20 best movies like Sidewalks of New York (2001)

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.

Though Rachel (Ginnifer Goodwin) 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 (Kate Hudson). Ramifications of the liaison threaten to destroy the women's lifelong friendship, while Ethan (John Krasinski), Rachel's confidant, harbors a potentially explosive secret of his own.

Sidney is a writer who's just left her L.A. Times music review gig to edit New York hip-hop magazine XXL. Dre is an executive with a hip-hop record company based in New York. They've known each other since they met as children, when both discovered hip-hop for the first time. Now that they're back together, they should be perfect for each other, except that Dre's about to marry lawyer Reese and Sidney claims not to be interested in Dre romantically. Meanwhile, Dre is growing increasingly restless with his company's focus on profit over artistry, which leads to signing the gimmicky duo Ren and Ten while ignoring the talented Chris

A group of thirtysomethings having problems with fidelity gets an opportunity to turn back the clock.

When her inability to commit leads to a breakup with her girlfriend, opera-loving writer Allegra winds up in the bed of amiable professor Philip. He is so smitten with Allegra that he dumps his lover, Grace (Justin Kirk), and convinces Allegra to continue their affair. When Allegra meets Grace, sparks fly, and she begins a parallel romance, unaware that her new lover is the woman Philip left to be with her.

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.

Cheated on, mistreated and stepped on, the women are holding their breath, waiting for the elusive "good man" to break a string of less-than-stellar lovers. Friends and confidants Vannah, Bernie, Glo and Robin talk it all out, determined to find a better way to breathe.

Sam has a problem with his roommates: they are disgusting, and don't seem to share his views on responsibility, privacy, and basic hygine. Such is his discomfort with his living arrangements that he agrees to share the occupancy of another flat: he gets two nights a week, the owner (a sleazy frat-boy yuppie named Brian, soon to be married) and Ellen (a would-be painter seeking relief from her boring marriage) each get their seperate nights in the flat. Things go extremely well until Sam and Brian swap nights without telling Ellen, who attributes the "nice" things that happen around the place to the slob Brian, while berating the responsible Sam for his hedonistic lifestyle.

Two literary women compete for 20 years: one writes for the critics; the other one, to get rich.

An aloof, struggling food photographer thinks he has found true love with a fiery grade-school teacher. At first, the relationship is all wine and roses, but as they realize they have little in common besides great sex, the romance wanes, and they struggle through a succession of break-ups and reunions as they try to work things out.

Dr. Henry Harriston is a successful psychoanalyst in New York City. When he is near a nervous breakdown, he arranges to change his flat with Beatrice Saulnier from France for a while. Both don't know each other and both find themselves deeply involved into the social settings of the other, because the decision to change their flats is made overnight. Could be the perfect amusement, but suddenly Henry finds himself beaten up by Beatrice' lover and Beatrice is considered to be Dr. Harriston's substitute by his clients...

Happily married for three years, Ann and David Smith live in New York. One morning Ann asks David if he had to do it over again, would he marry her? To her shock, he answers, "No". Later that day, they separately discover that, due to a legal complication, they are not legally married.

Otto Wall is just a little unlucky in life, and unbeknownst to him, in love. When his wife suddenly asks for a divorce, he bounces between a search for answers, desperate attempts to stay connected to his daughter, and his fateful reentry into the dating pool.

A modern reimagining of the classic romantic comedy, this contemporary version closely follows new love for two couples as they journey from the bar to the bedroom and are eventually put to the test in the real world.

Nora Wilder (Parker Posey), a single, career woman works at a Manhattan boutique hotel where her excellent skills in guest relations lack in the romantic department. If it is not her loving and dominant mother (Gena Rowlands) attempting to set her up that consistently fail, she has her friend’s (Drea de Matteo) disastrous blind dates to rely on as a backup for further dismay. She's surrounded by friends who are all happily engaged or romantically involved and somehow, love escapes Nora -- until she meets an unusual Frenchman (Melvil Poupaud) who helps her discover life beyond her self-imposed boundaries.

Linus and David Larrabee are the two sons of a very wealthy family. Linus is all work -- busily running the family corporate empire, he has no time for a wife and family. David is all play -- technically he is employed by the family business, but never shows up for work, spends all his time entertaining, and has been married and divorced three times. Meanwhile, Sabrina Fairchild is the young, shy, and awkward daughter of the household chauffeur, who has been infatuated with David all her life, but David hardly notices her -- "doesn't even know I exist" -- until she goes away to Paris for two years, and returns an elegant, sophisticated, beautiful woman. Suddenly, she finds that she has captured David's attention, but just as she does so, she finds herself falling in love with Linus, and she finds that Linus is also falling in love with her.

Pampered Manhattan housewife Desiree Harper has it all. That is until her husband unexpectedly dumps her for his acupuncturist. Faced with an airtight prenup, Desiree reluctantly lands a job making cupcakes at her father's bakery in Flemington, NJ. She soon discovers there's more to life than 5th Avenue and true love can be even sweeter in small town America.

Christian is a Copenhagen wine seller on the brink of bankruptcy. Equally unsuccessful in just about every other aspect of life, it has been 17months since his wife Anna left him. Anna works as a soccer agent in Buenos Aires and now lives a life of luxury with Argentina's top player Juan Diaz. Then one day Christian and their 16-year-old son Oscar get on a plane to Buenos Aires. Christian arrives under the pretense of wanting to sign the divorce papers, but in truth, he wants to try to win Anna back.

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

In Los Angeles, Max Carlyle makes a good living directing commercials and has a happy home life with his wife, Mimi, and two children. When Carlyle travels to New York City to visit his friend Charlie, who has been diagnosed with AIDS, he has repeat run-ins with a beautiful woman, Karen, and eventually sleeps with her. Though he goes home the next day and doesn't return until a year later, Carlyle's infidelity still lingers.

A nutty inventor, his frustrated wife, a philosopher cousin, his much younger fiancée, a randy doctor, and a free-thinking nurse spend a summer weekend in and around a stunning - and possibly magical - country house.

A semi-autobiographical depiction of the filmmaker's own predatory sexual history, Manhattan explores how the life of a middle-aged television writer abusing a teenage girl is further complicated when he falls in love with his best friend's mistress.

A man with a "doormat" personality tries standing up for himself for a change in this comedy. Mild mannered tax accountant Elliot Sherman is what he calls a "Baxter": the kind of calm, unexciting fellow who "wears sock garters" and "enjoys raking leaves." Loved by bosses and parents, Elliot is a perfectly nice guy. And that's his problem.

A romantic comedy about a mysterious love letter that turns a sleepy New England town upside down.

Rick is a screenwriter living in Los Angeles. While successful in his career, his life feels empty. Haunted and confused, he finds temporary solace in the decadent Hollywood excess that defines his existence. Women provide a distraction to his daily pain, and every encounter brings him closer to finding his place in the world.

Gloria is a 58-year-old divorcée. Her children have all left home but she has no desire to spend her days and nights alone. Determined to defy old age and loneliness, she rushes headlong into a whirl of singles’ parties on the hunt for instant gratification – which only leads to repeated disappointment and enduring emptiness. But when Gloria meets Rodolfo, an ex-naval officer seven years her senior, she begins to imagine the possibility of a permanent relationship.

When Lenny and his wife, Amanda, adopt a baby, Lenny realizes that his son is a genius and becomes obsessed with finding the boy's biological mother in hopes that she will be brilliant too. But when he learns that Max's mother is Linda Ash, a kindhearted prostitute and porn star, Lenny is determined to reform her immoral lifestyle. A Greek chorus chimes in to relate the plot to Greek mythology in this quirky comedy.

Unfounded suspicions lead a married couple to begin divorce proceedings, whereupon they start undermining each other's attempts to find new 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.

In 1950s New York, a department-store clerk who dreams of a better life falls for an older, married woman.

Maggie's plan to have a baby on her own is derailed when she falls in love with John, a married man, destroying his volatile marriage to the brilliant and impossible Georgette. But one daughter and three years later, Maggie is out of love and in a quandary: what do you do when you suspect your man and his ex wife are actually perfect for each other?

Jo is chained down in a dead end supermarket job while all her friends are all out on their own separate adventures. But a chance encounter with some diamond thieves sends their separate worlds on a collision course with not only each other, but fate itself.

A witty, romantic, and very dangerous love story about chance meetings, instant attractions, and casual betrayals. Two couples disintegrate when they begin destructive adulterous affairs with each other.

Millionaire industrialist Steven Taylor is a man who has everything but what he craves most: the love and fidelity of his wife. A hugely successful player in the New York financial world, he considers her to be his most treasured acquisition. But she needs more than simply the role of dazzling accessory.

Based on Evelyn Waugh's 1945 classic British novel, Brideshead Revisited is a poignant story of forbidden love and the loss of innocence set in England prior to the Second World War.

A mild mannered film critic is dumped by his wife and his ego is crushed. His hero persona is the tough guy played by Humphrey Bogart in many of his movies and the apparition of Bogart begins showing up to give him advice. With the encouragement of his two married friends, he actually tries dating again, with less than satisfactory results, until he relaxes.

After a one-night stand a couple is faced with the terrifying possibility of what they really want.

Porter Stoddard is a well-known New York architect who is at a crossroads... a nexus where twists and turns lead to myriad missteps some with his wife Ellie, others with longtime friends Mona and her husband Griffin. Deciding which direction to take often leads to unexpected encounters with hilarious consequences.

Three to one may sound like fairly good odds, but it depends on the game. When the "one" is one very irresistible woman and the "three" are three hopelessly smitten guys, the deck is pretty stacked. In the battle of the sexes, the first rule is to never underestimate the power of a woman.

Publishing assistant Brett Eisenberg wants to be a big-time editor. However, she lacks self-confidence, a problem that isn't helped by her new, overbearing boss. Brett soon enters into a relationship with Archie, an older man who has plenty of his own issues, including alcoholism, diabetes and a difficult relationship with his daughter. Intent on helping Archie get past his problems, she turns to her dying father for advice.

A British writer struggles to fit in at a high-profile magazine in New York. Based on Toby Young's memoir "How to Lose Friends & Alienate People".

When a rich woman's ex-husband and a tabloid-type reporter turn up just before her planned remarriage, she begins to learn the truth about herself.

When struggling, out of work actor Michael Dorsey secretly adopts a female alter ego -- Dorothy Michaels -- in order to land a part in a daytime drama, he unwittingly becomes a feminist icon and ends up in a romantic pickle.

A pregnant New York social worker begins to develop romantic feelings for her gay best friend, and decides she'd rather raise her child with him, much to the dismay of her overbearing boyfriend.

A man wakes up in an alley, bleeding and with no memory of who he is. He stumbles into a coffee shop and is befriended by a charitable ex-nun who is failing in her attempts to write marketable pornography.

Although strangers Sara and Jonathan are both already in relationships, they realize they have genuine chemistry after a chance encounter – but part company soon after. Years later, they each yearn to reunite, despite being destined for the altar. But to give true love a chance, they have to find one another again.

Fortune hunter Holly Golightly finds herself captivated by aspiring writer Paul Varjak, who's moved into her building on a wealthy woman's dime. As romance blooms between Paul and Holly, Doc Golightly shows up on the scene, revealing Holly's past.

A story based on the life of a struggling Long Island single mom who became one of the country's most successful entrepreneurs.

The lives of two struggling musicians, who happen to be brothers, inevitably change when they team up with a beautiful, up-and-coming singer.

A philosophical burlesque, Human Nature follows the ups and downs of an obsessive scientist, a female naturalist, and the man they discover, born and raised in the wild. As scientist Nathan trains the wild man, Puff, in the ways of the world - starting with table manners - Nathan's lover Lila fights to preserve the man's simian past, which represents a freedom enviable to most.