Movies Like The Gentleman

If you liked The Gentleman (2000), a movie directed by Sam Serafy and Jonathan Spottiswoode, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
The Dead (1987)
★ 6.9/10
After a convivial holiday dinner party, things begin to unravel when a husband and wife address some prickly issues concerning their marriage.
2
Born Yesterday (1950)
★ 7.3/10
Uncouth, loud-mouth junkyard tycoon Harry Brock descends upon Washington D.C. to buy himself a congressman or two, bringing with him his mistress, ex-showgirl Billie Dawn.
3
My Big Fat Greek Wedding 3 (2023)
★ 5.9/10
Following the death of their patriarch Gus, the Portokalos family travels to Greece for a family reunion, and to deliver Gus' journal to his old friends.
4
Mamma Mia! Here We Go Again (2018)
★ 7.1/10
Five years after meeting her three fathers, Sophie Sheridan prepares to open her mother’s hotel. In 1979, young Donna Sheridan meets the men who each could be Sophie’s biological father.
5
My Best Friend's Wedding (1997)
★ 6.6/10
When she receives word that her longtime platonic pal Michael O'Neal is getting married to debutante Kimberly Wallace, food critic Julianne Potter realizes her true feelings for Michael -- and sets out to sabotage the…
6
The Age of Innocence (1993)
★ 7/10
In 19th century New York high society, a young lawyer falls in love with a woman separated from her husband, while he is engaged to the woman's cousin.
7
5 to 7 (2014)
★ 7.1/10
A young writer begins an affair with an older woman from France whose open marriage to a diplomat dictates that they can meet only between the hours of 5 p.m. to 7 p.m.
8
Class (1983)
★ 6/10
Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip's urging, the inexperienced Jonathan is emboldened to seek out older women in the…
9
My Fair Lady (1964)
★ 7.5/10
A snobbish phonetics professor agrees to a wager that he can take a flower girl and make her presentable in high society.
10
Frankie and Johnny (1991)
★ 6.8/10
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, he develops an attraction for Cora's friend…
11
Barefoot in the Park (1967)
★ 7.1/10
In this film based on a Neil Simon play, newlyweds Corie, a free spirit, and Paul Bratter, an uptight lawyer, share a sixth-floor apartment in Greenwich Village. Soon after their marriage, Corie tries to find a…
12
Materialists (2025)
★ 6.3/10
A young, ambitious New York City matchmaker finds herself torn between the perfect match and her imperfect ex.
13
She's Funny That Way (2015)
★ 5.9/10
On the set of a playwright's new project, a love triangle forms between his wife, her ex-lover, and the call girl-turned-actress cast in the production.
14
Someone Great (2019)
★ 6.4/10
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…
15
Romance & Cigarettes (2006)
★ 6.1/10
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…
16
Prom (2011)
★ 6.1/10
At “Prom,” every couple has a story and no two are exactly alike. As the big dance approaches for Nova Prescott, it’s a battle of wills as she finds herself drawn to the guy who gets in the way of her perfect prom…
17
My Sassy Girl (2008)
★ 6.8/10
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
18
How to Be Single (2016)
★ 6.3/10
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…
19
F Valentine's Day (2026)
★ 6.1/10
Gina hates her Valentine's Day birthday and travels to Greece to prevent her boyfriend's proposal. With help from vacationers Johnny and his sister Mickey, she schemes to delay it – while questioning her relationship.
20
72 HOURS (2026)
★ 6.8/10
To save his career, a 40-year-old ad exec joins a crew of twentysomethings for a wild Miami bachelor party after they mistakenly add him to a group chat.