Movies like Chance of a Lifetime (1998)
The best movies like Chance of a Lifetime (1998) are Love & Sex (2000), He Said, She Said (1991) and Enemies, a Love Story (1989). If Chance of a Lifetime hooked you with its comedy and drama, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedLove Don't Co$t a Thing (2003)7.7/10 from 743 votes
- NewestThe Baltimorons (2025)Released 2025
Love & Sex (2000)
When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back over her own various experiences, and to wondering if she is in much of a position to write on the subject.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisHe Said, She Said (1991)
Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions alongside each other, which leads to a similarly combative local TV show. At the same time their initial indifference to each other looks like it may evolve into something more romantic.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisEnemies, a Love Story (1989)
A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisJack Goes Boating (2010)
A limo driver's blind date sparks a tale of love, betrayal, friendship and grace—centered on two working-class New York City couples.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisWalking and Talking (1996)
Just as Amelia thinks she's over her anxiety and insecurity, her best friend announces her engagement, bringing her anxiety and insecurity right back.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisBroken English (2007)
Nora Wilder is freaking out. Everyone around her is either in a relationship, married, or has children, while she's in her thirties, alone with job she's outgrown and a mother who constantly reminds her of it all. Not to mention her best friend Audrey's "perfect marriage". But after a series of disastrous dates, Nora unexpectedly meets Julien, a quirky Frenchman who opens her eyes to a lot more than love.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisNumb (2007)
Hudson Milbank is a successful Hollywood screenwriter who suddenly and strangely finds himself without any emotional feelings. He tries doctor after doctor and shrink after shrink, but nothing works. The Golf Channel, lesbian exercise classes and a dizzying variety of pills get him through the day, but don't quite solve his problem. His writing partner tries everything to get him back to normal, but it's not until Hudson meets Sara that he finds a real motivation to get better and to actually start feeling again. From the writer of Deuce Bigalow, comes NUMB, a romantic comedy following an unusual man looking for strange love.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisSidewalks of New York (2001)
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisCamille (2008)
A twisted honeymoon adventure about a young couple on their way to Niagara Falls.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisYou Will Meet a Tall Dark Stranger (2010)
Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisThe Baltimorons (2025)
A newly sober man's Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisPeace, Love & Misunderstanding (2011)
A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisLove Don't Co$t a Thing (2003)
A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisA California Christmas: City Lights (2021)
Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisIrreplaceable You (2018)
A stunning cancer diagnosis spurs Abbie to seek a future girlfriend for fiancé and childhood sweetheart Sam, who's clueless when it comes to dating.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisCyrus (2010)
With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before long, the two are locked in a battle of wits for the woman they both love-and it appears only one man can be left standing when it's over.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisA California Christmas (2020)
With his carefree lifestyle on the line, a wealthy charmer poses as a ranch hand to get a hardworking farmer to sell her family’s land before Christmas.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Best You Can (2025)
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside down by the arrival of sharp but chronically underachieving security guard Stan Olszewski in this smart rom-com that reunites Bacon and Sedgwick on screen for the first time in 20 years.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisJust Before I Go (2015)
Ted Morgan has been treading water for most of his life. After his wife leaves him, Ted realizes he has nothing left to live for. Summoning the courage for one last act, Ted decides to go home and face the people he feels are responsible for creating the shell of a person he has become. But life is tricky. The more determined Ted is to confront his demons, to get closure, and to withdraw from his family, the more Ted is yanked into the chaos of their lives. So, when Ted Morgan decides to kill himself, he finds a reason to live.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisL.A. Without a Map (1999)
An aspiring Hollywood actress, on a visit to a charming North England town, has a brief fling with the town undertaker, who also writes obituaries for the local paper. Returning home, where she works as a waitress at a Japanese restaurant, she tells everyone about the handsome "writer" she met on her trip. Unfortunately, he decides to follow her back to Hollywood, setting up the expected light romantic comedy with asides as the newcomer gains experience about the goings on in Hollywood.
Why it matches: Recommended by TMDB viewers · both drama & comedy
SnoozefestMovies like thisAmour Fou (2014)
Heinrich wishes to conquer death through love, and when he meets Henriette, the wife of a business acquaintance, she expresses interest in a suicide pact when she learns she has a terminal illness.
Why it matches: Similar story and style · both drama & comedy
Popcorn FlickMovies like thisThe Belt (1989)
Vittorio, an American novelist teaching in Rome, meets the beautiful but damaged Bianca and they rapidly fall into an urgent, tempestuous affair. He's hesitant over their relationship since she seems to thrive on conflict and is constantly baiting him into physical altercation. Bianca gives Vittorio an exquisite leather belt as a gift; he knows immediately that she wants him to whip her with it. Driven by his craving for her, Vittorio complies to Bianca's desire. Their relationship escalates into a dark realm of S&M which becomes more and more self-destructive.
Why it matches: Similar story and style · both drama & romance
Bird People (2014)
An overstressed American businessman and a French chambermaid make a connection at an airport hotel in Paris.
Why it matches: Similar story and style · both drama & romance
SnoozefestMovies like thisFine (2016)
A short film about the endless fight of two woman. A Mexican and Bosnian co-production set in Sarajevo.
Why it matches: Similar story and style · both drama & comedy
Zoo (1988)
Martina lives in the Rome's zoo, because her father is the guardian. She becomes friend with a young Slavic escaped from a gypsy camp. When the police arrives searching for the kid, they run away riding an elephant!
Why it matches: Similar story and style · both comedy & drama
Butch Jamie (2008)
The film follows the story of Jamie, a struggling butch lesbian actress who gets cast as a man in a film. The main plot is a romantic comedy between Jamie's male alter-ego, "Male Jamie," and Jill, a heterosexual woman on set. The film's subplots include Jamie's bisexual roommate Lola and her cat actor Howard, Lola's abrasive butch German girlfriend Andi, and Jamie's gay Asian friend David.
Why it matches: Similar story and style · both comedy & romance
Four Rooms (1995)
It's Ted the Bellhop's first night on the job...and the hotel's very unusual guests are about to place him in some outrageous predicaments. It seems that this evening's room service is serving up one unbelievable happening after another.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like thisKiss Me, Frog (2000)
Modern version of The Frog King. Out of an impulse, 15-year-old Anna kisses a frog which then turns into a prince. But the curse is not solved that easily.
Why it matches: Similar story and style · both comedy
A Girl at My Door (2014)
Sent from Seoul to serve in a remote coastal village, a policewoman gets involved in the life of a mysterious teenage girl who is abused by both her father and her grandmother.
Why it matches: Similar story and style · both drama
Popcorn FlickMovies like thisGirlhood (2014)
Oppressed by her family setting, dead-end school prospects and the boys law in the neighborhood, Marieme starts a new life after meeting a group of three free-spirited girls. She changes her name, her dress code, and quits school to be accepted in the gang, hoping that this will be a way to freedom.
Why it matches: Similar story and style · both drama
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Chance of a Lifetime?
The closest matches to Chance of a Lifetime are Love & Sex (2000), He Said, She Said (1991) and Enemies, a Love Story (1989). Below are 27 more, each with the reason it matches.
What should I watch after Chance of a Lifetime?
Start with Love & Sex (2000), the closest match to Chance of a Lifetime.
What is the highest-rated movie like Chance of a Lifetime?
Love Don't Co$t a Thing (2003), rated 7.7/10 by 743 TMDB users.
What is the newest movie like Chance of a Lifetime?
The Baltimorons (2025) is the most recent release on this list.
Are there English movies like Chance of a Lifetime?
Yes: Love & Sex (2000), He Said, She Said (1991) and Enemies, a Love Story (1989).
How are movies similar to Chance of a Lifetime chosen?
First come films that Trakt’s viewers watch alongside Chance of a Lifetime, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.