Movies Like The Winslow Boy

If you liked The Winslow Boy (1958), a comedy and drama movie directed by Alex Segal, 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 Duke (2021)
★ 6.9/10Also comedy and drama
In 1961, a 60-year-old taxi driver steals Goya’s portrait of the Duke of Wellington from the National Gallery in London. It was the first (and remains the only) theft in the Gallery’s history. What happens next becomes…
2
Oslo (2021)
★ 6.6/10Also drama and history
The true story of negotiations between implacable enemies — the secret back-channel talks, unlikely friendships and quiet heroics of a small but committed group of Israelis, Palestinians and one Norwegian couple that…
3
Savage House (2026)
★ 7/10Also comedy and drama
Against the backdrop of 18th century England, a massive pox outbreak, and Jacobite uprising – Sir Chauncey Savage and Lady Savage blindly pursue a better life. It's not without a tinge of irony that their family name…
4
Adventures of a Mathematician (2021)
★ 6.1/10Also drama and history
The warmhearted story of Polish immigrant and mathematician Stan Ulam, who moved to the U.S. in the 1930s. Stan deals with the difficult losses of family and friends all while helping to create the hydrogen bomb and…
5
Lady Windermere's Fan (1925)
★ 6.9/10Also comedy and drama
A society woman believes her husband is having an affair, a misconception which may have dire personal consequences for all involved.
6
Landline (2017)
★ 6.2/10Also comedy and drama
A teenager living with her sister and parents in Manhattan during the 1990s discovers that her father is having an affair.
7
The Madness of King George (1994)
★ 6.8/10Also comedy and drama
Aging King George III of England is exhibiting signs of madness, a problem little understood in 1788. As the monarch alternates between bouts of confusion and near-violent outbursts of temper, his hapless doctors…
8
One Chance (2013)
★ 6.7/10Also drama and comedy
This film follows the remarkable and inspirational true story of Paul Potts, a shy, bullied shop assistant by day and an amateur opera singer by night.
9
Munich - The Edge of War (2021)
★ 6.9/10Also drama and history
At the tense 1938 Munich Conference, former friends who now work for opposing governments become reluctant spies racing to expose a Nazi secret.
10
Julia (1977)
★ 6.5/10Also drama and history
At the behest of an old and dear friend, playwright Lillian Hellman undertakes a dangerous mission to smuggle funds into Nazi Germany.
11
Cats (1998)
★ 7.2/10Also drama and comedy
"Jellicle" cats join for a Jellicle ball where they rejoice with their leader, Old Deuteronomy. One cat will be chosen to go to the "Heavyside Layer" and be reborn.
12
Family Weekend (2013)
★ 6.3/10Also comedy and drama
A 16-year-old girl takes her parents hostage after they miss her big jump-roping competition.
13
Radium Girls (2020)
★ 6.6/10Also drama and history
Young women toiling in a factory are exposed to hazardous material which takes a disastrous toll on their health.
14
Don't Think Twice (2016)
★ 6.4/10Also comedy and drama
An improv group deals with several crises, including the loss of their lease and one member hitting the big time.
15
The Clique (2008)
★ 5.9/10Also comedy and drama
A young girl tries to fit in with a clique of popular middle school girls after moving into the guest house of one of their homes.
16
Feel the Beat (2020)
★ 7.5/10Also comedy and drama
After failing to make it on Broadway, April returns to her hometown and reluctantly begins training a misfit group of young dancers for a competition.
17
Giant (2026)
★ 6.9/10Also drama and history
Follows Prince Naseem Hamed from his humble beginnings on the tough working-class streets of Sheffield and his discovery by Ingle, himself a steel industry worker turned boxing trainer. Their unlikely partnership…
18
Game Change (2012)
★ 6.9/10Also drama and comedy
During the Republican run of the 2008 Presidential election, candidate John McCain picks a relative unknown, Alaskan governor Sarah Palin, to be his running mate. As the campaign kicks into high gear, her lack of…
19
Prizefighter: The Life of Jem Belcher (2022)
★ 6.2/10Also history and drama
At the turn of the 19th century, Pugilism was the sport of kings and a gifted young boxer fought his way to becoming champion of England.
20
SubUrbia (1997)
★ 6.2/10Also comedy and drama
A group of suburban teenagers try to support each other through the difficult task of becoming adults.