Movies Like Lost and Won

If you liked Lost and Won (1911), a movie, 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
True Grit (1969)
★ 7.3/10
The murder of her father sends a teenage tomboy on a mission of 'justice', which involves avenging her father's death. She recruits a tough old marshal, 'Rooster' Cogburn because he has 'true grit', and a reputation of…
2
The Great Gatsby (2013)
★ 7.3/10
Nick Carraway arrives in New York in 1922, an era of loose morals, glittering jazz and bootleg kings. Chasing his own American Dream, Nick encounters the mysterious millionaire Gatsby and his bewitching cousin Daisy…
3
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.
4
Great Expectations (2012)
★ 6.4/10
Orphan Pip discovers through lawyer Mr. Jaggers that a mysterious benefactor wishes to ensure that he becomes a gentleman. Reunited with his childhood patron, Miss Havisham, and his first love, the beautiful but…
5
An Autumn Romance (2021)
★ 7/10
When librarian Taylor Harris suddenly loses her job, she decides to visit her brother in a small town in Montana. There, she gets involved in the fight to help save her brother's hotel from tycoon Joel Sheenan, who…
6
Train Dreams (2025)
★ 7.3/10
A logger leads a life of quiet grace as he experiences love and loss during an era of monumental change in early 20th-century America.
7
Pretty Woman (1990)
★ 7.4/10
Vivian is a carefree, streetwise diamond in the rough when she meets sophisticated billionaire Edward in a chance encounter that turns into a week-long business arrangement. But Vivian's energetic spirit challenges…
8
Jack Hunter and the Lost Treasure of Ugarit (2010)
★ 6.5/10
Jack Hunter, an adventurous treasure seeker, goes to Syria after his mentor and father figure Professor Fredrick Shaffer is killed. Professor Frederick Shaffer believed that the people of Ugarit, a town in Syria that…
9
Sherlock Jr. (1924)
★ 8/10
A film projectionist longs to be a detective, and puts his meager skills to work when he is framed by a rival for stealing his girlfriend's father's pocketwatch.
10
The Adjustment Bureau (2011)
★ 6.8/10
A man glimpses the future Fate has planned for him – and chooses to fight for his own destiny. Battling the powerful Adjustment Bureau across, under and through the streets of New York, he risks his destined greatness…
11
The Purple Rose of Cairo (1985)
★ 7.4/10
Cecilia is a waitress in New Jersey, living a dreary life during the Great Depression. Her only escape from her mundane reality is the movie theatre. After losing her job, Cecilia goes to see 'The Purple Rose of Cairo'…
12
Our Kind of Traitor (2016)
★ 6/10
A young Oxford academic and his attorney girlfriend holiday in Morocco. They bump into a Russian millionaire who owns a peninsula and a diamond watch. He wants a game of tennis. What else he wants propels the lovers on…
13
Snoopy Presents: It's the Small Things, Charlie Brown (2022)
★ 7.3/10
Charlie Brown is determined to win the big baseball game. But things turn into a fiasco right before the matchup, when Sally bonds with a little flower on the pitcher's mound and vows to protect it at all costs.
14
Lady Chatterley's Lover (2015)
★ 6.3/10
An early-20th-century tale of love across class boundaries which tells the legendary and romantic story of Lady Chatterley’s affair with her gamekeeper. Jed Mercurio’s adaptation of DH Lawrence’s classic.
15
Playing It Cool (2014)
★ 5.9/10
A young man meets and instantly falls in love with an engaged woman.
16
The White Tiger (2021)
★ 7/10
An ambitious Indian driver uses his wit and cunning to escape from poverty and rise to the top. An epic journey based on the New York Times bestseller.
17
Sabrina (1954)
★ 7.5/10
After two years in Paris, chauffeur's daughter Sabrina returns home elegantly transformed and immediately catches the attention of David, the playboy son of her father's rich employers. David woos and wins Sabrina, who…
18
Paradise (1982)
★ 6/10
After their caravan is attacked and their respective families butchered by Arab marauders, teenagers David and Sarah flee across the desert. But the desert is filled with danger from the elements, animals and the…
19
That Touch of Mink (1962)
★ 6.5/10
Cathy Timberlake is en route to a job interview when a car transporting businessman Philip Shayne covers her in mud. He sends his assistant, Roger, to apologize, but upon meeting Cathy, Roger knows that she would be a…
20
The Time Traveler's Wife (2009)
★ 7/10
Due to a genetic disorder, handsome librarian Henry DeTamble involuntarily zips through time, appearing at various moments in the life of his true love, the beautiful artist Clare Abshire.