20 best movies like Simply Irresistible (1999)

Victor Bukowski is an out-of-work actor with problems. He's got a lousy agent, he has a habit of falling out with directors and he's still in love with his ex-girlfriend. However, Victor is about to embark on an unexpected emotional journey which will make him confront his future and his past mistakes.

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.

The night after another unsatisfactory New Year party, Tim's father tells his son that the men in his family have always had the ability to travel through time. Tim can't change history, but he can change what happens and has happened in his own life – so he decides to make his world a better place... by getting a girlfriend. Sadly, that turns out not to be as easy as he thinks.

When Elliot, a brash 23-year-old living carefree in New York City, meets the sensible Mia and receives a damning diagnosis all in the same week, his world is turned completely upside down. But as their love blossoms amidst the chaos of his treatment, they discover that Elliot's illness is not the real test of their relationship – it's everything else.

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

A Russian circus visits the US. A clown wants to defect, but doesn't have the nerve. His saxophone playing friend however comes to the decision to defect in the middle of Bloomingdales. He is befriended by the black security guard and falls in love with the Italian immigrant from behind the perfume counter. We follow his life as he works his way through the American dream and tries to find work as a musician.

When a professional couple, who have lived and worked together for many years, finally decide to marry, their sudden betrothal causes many unexpected difficulties. They soon find that being married is often quite different from being "best friends."

A young woman with Asperger's tries to find her first boyfriend with a little help from her older sister.

Xavier is a 40-year-old father of two who still finds life very complicated. When the mother of his children moves to New York, he can't bear them growing up far away from him and so he decides to move there as well.

With the help of a talking freeway billboard, a "wacky weatherman" tries to win the heart of an English newspaper reporter, who is struggling to make sense of the strange world of early-90s Los Angeles.

Calvin is a young novelist who achieved phenomenal success early in his career but is now struggling with his writing – as well as his romantic life. Finally, he makes a breakthrough and creates a character named Ruby who inspires him. When Calvin finds Ruby, in the flesh, sitting on his couch about a week later, he is completely flabbergasted that his words have turned into a living, breathing person.

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.

After spending eight months in a mental institution, a former teacher moves back in with his parents and tries to reconcile with his ex-wife.

Spoiled playboy Henry van Cleve dies and arrives at the entrance to Hell, a final destination he is sure he deserves after living a life of profligacy. The devil, however, isn't so sure Henry meets Hell's standards. Convinced he is where he belongs, Henry recounts his life's deeds, both good and bad, including an act of indiscretion during his 25-year marriage to his wife, Martha, with the hope that "His Excellency" will arrive at the proper judgment.

Three World War II buddies promise to meet at a specified place and time 10 years after the war. They keep their word only to discover how far apart they've grown. But the reunion sparks memories of youthful dreams that haven't been fulfilled -- and slowly, the three men reevaluate their lives and try to find a way to renew their friendship.

The film tells the story of quick-witted teen Mark, contentedly living the same day in an endless loop whose world is turned upside-down when he meets mysterious Margaret also stuck in the time loop. Mark and Margaret form a magnetic partnership, setting out to find all the tiny things that make that one day perfect. What follows is a love story with a fantastical twist, as the two struggle to figure out how -- and whether -- to escape their never-ending day.

Gary, a musician, is trapped in an unhappy relationship with his live-in lover, Dora. He becomes enthralled with a beautiful seductress who enters his dreams, and tries to control his dream-state so he can spend more and more time with her. When Gary sees his mystery woman's face on a bus billboard, he discovers she is real, and fate brings him an opportunity to meet her.

When a chance encounter brings together the cynical Dell and the quick-witted Kimberly, the stage is set for a tempestuous love affair that unfolds like a puzzle. As the film zigzags back and forth in time-from a meteor shower in LA, to an encounter in a Paris hotel room, to a fateful phone call-an unforgettable portrait of a relationship emerges.

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.

Miranda Presley moves from New York to Nashville to become a songwriter. At an unsuccessful audition she meets James Wright, a promising newcomer. After only a few days they marry but start to quickly regret it.

Leelee Sobieski is brash, abrasive and vulnerable as a teenage child of divorce who hides her pain behind a mask of hard-edged gothic rebellion. Albert Brooks plays a man who is her total opposite, a precise and well-ordered menswear store owner of forty-nine who manages limited expectations and protects lonely secrets with pleasant ritual and quiet, ironic reserve. These two total opposites collide in conflict then come together in a surprising alliance, changing each other's lives forever.

Urban horticulturalist Brontë Mitchell has her eye on a gorgeous apartment, but the building's board will rent it only to a married couple. Georges Fauré, a waiter from France whose visa is expiring, needs to marry an American woman to stay in the country. Their marriage of convenience turns into a burden when they must live together to allay the suspicions of the immigration service, as the polar opposites grate on each other's nerves.

Depressed and jaded after being dumped by her married boyfriend, aging beauty Minnie Moore wonders if she'll ever find love. After shaggy-haired parking lot attendant Seymour Moskowitz comes to her defense from an angry and rebuffed blind date, he falls hopelessly in love with her despite their myriad differences. Minnie reluctantly agrees to a date with Moskowitz, and, slowly but surely, an unlikely romance blossoms between the two.

It's a movie for everyone whose life has been thrown off-course, out of whack, or simply not turned out the way they planned it. In other words, it's a movie for everyone, period. Set in suburban Long Island in the summer of 2002, with the psychic wounds of 9/11 still fresh, A Little Help is a story that takes a comic, searching and profoundly empathetic look at a few pivotal months in the life of dental hygienist Laura Pehlke (Jenna Fischer)-an ordinary woman whose life suddenly flies off the rails-and her heroic efforts to re-establish a sense of security and normalcy for herself and her son.

A businessman is reunited with the four lost souls who were his guardian angels during childhood, all with a particular purpose to joining the afterlife.

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 recent college graduate sets out to win back the girl of his dreams.

On a flight from Los Angeles to New York, Oliver and Emily make a connection, only to decide that they are poorly suited to be together. Over the next seven years, however, they are reunited time and time again, they go from being acquaintances to close friends to ... lovers?

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.

A sudden loss disrupts Carol’s orderly life, propelling her into the dating world for the first time in 20 years. Finally living in the present tense, she finds herself swept up in not one, but two unexpected relationships that challenge her assumptions about what it means to grow old.

As her marriage dissolves, a Manhattan writer takes driving lessons from a Sikh instructor with marriage troubles of his own. In each other's company they find the courage to get back on the road and the strength to take the wheel.

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.

After attending their friend Elise's (Sudano) wedding to Nate (Bishop) on New Year's Eve, Trista (Hall), a career-­driven talent agent, Viviane (Scott), a successful gossip columnist, and Amaya (Cooper), a struggling actress, make a pact to get married within the year to either a new love or a man waiting in the wings. But the close friends face their own set of challenges - Trista has not gotten over her commitment-­phobic ex-­boyfriend Damon (White), Viviane is secretly in love with Sean (George), the father of her son, and Amaya is desperate to break up her boyfriend Keith's (Sanders) unhappy marriage so they can live happily ever after. Each woman starts the year with high hopes and dreams of what will happen over the next 12 months... but will they all make it to the altar?

A woman on the brink of a marriage proposal is told by a friend that she should date other men before spending the rest of her life with her boyfriend.

A clinically depressed teenager gets a new start after he checks himself into an adult psychiatric ward.

When college friends reunite after 15 years over the Christmas holidays, they discover just how easy it is for long-forgotten rivalries and romances to be reignited.

Three 40-something women in a small English town meet weekly for a ritual of gin, cigarettes, and sweets -- and swapped stories arguing which of them has the most pathetic love life. Kate is headmistress at the local school; her best friends are the town's police chief and a cynical, thrice-divorced doctor.

Patrick returns to San Francisco for the first time in almost a year to celebrate a momentous event with his old friends. In the process, he must face the unresolved relationships he left behind and make difficult choices about what’s important to him.

When the grim reaper comes to collect the soul of megamogul Bill Parrish, he arrives with a proposition: Host him for a "vacation" among the living in trade for a few more days of existence. Parrish agrees, and using the pseudonym Joe Black, Death begins taking part in Parrish's daily agenda and falls in love with the man's daughter. Yet when Black's holiday is over, so is Parrish's life.

Reunited after 15 years, famous chef Sasha and hometown musician Marcus feel the old sparks of attraction but struggle to adapt to each other's worlds.

Martha is a single woman who lives for one passion: cooking. The head chef at a chic restaurant, Martha has no time for anything - or anyone - else. But Martha's solitary life is shaken when a fateful accident brings her sister's eight-year-old daughter, Lina, to her doorstep.

A working girl from New Jersey looks for love with a fast-lane Manhattan salesman from Queens.

When a young airman miraculously survives bailing out of his aeroplane without a parachute, he falls in love with an American radio operator. But the officials in the other world realise their mistake, and dispatch an angel to collect him.

A small suburban town receives a visit from a castaway unfinished science experiment named Edward.

Gray Wheeler just lost everything. But it could be the best thing that ever happened to her. After the death of her fiancé, Gray moves in with her late love's best friends. While Sam and Dennis do their best to cheer Gray up, Fritz doesn't seem to care. Once Gray breaks through Fritz's defenses, however, she finally sees why her fiancé thought so highly of him. As they spend more time together, Gray learns that her chances for love have not died out with her fiancé. But when some surprise guests show up on their doorstep, it'll take the love of all of her new friends to help Gray learn that life may be messy, but love is messier.

The film follows a man with an unwanted gift for healing who meets a teenager with cancer who helps him to find himself.

"Hair" is a 1979 musical war comedy-drama film adaptation of the 1968 Broadway musical "Hair: An American Tribal Love-Rock Musical" about a Vietnam War draftee, Claude, who meets and befriends a tribe of long-haired hippies on his way to the army induction center. Claude heads to New York upon receiving his draft notice, leaving the family ranch in Oklahoma. He arrives in New York where he is rapidly indoctrinated into the youth subculture before reporting in for boot camp.

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.

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.

Book superstore magnate, Joe Fox and independent book shop owner, Kathleen Kelly fall in love in the anonymity of the Internet – both blissfully unaware that he's putting her out of business.