Related Titles

Movies Like Sir Highwayman

Find movies like Sir Highwayman using TMDB similarity plus Movie Rankings community context. Our top current pick is Penny of Top Hill Trail. Browse 18 related titles with direct links to rankings, cast pages, and matchup data.

These picks blend TMDB similar-title seeds with Movie Rankings community ranking context.

Next Best Actions

Explore Language Rankings

Recommended If You Liked Sir Highwayman
TMDB Similar

Penny of Top Hill Trail

1921

Penny arrives in the West by aeroplane. She is considered a suspicious character and thrown into jail. Kurt Walters, a ranch foreman and deputy sheriff, discovers that she is the same girl that his friend, Jo Gary, met in Chicago. Gary fell in love with her, but she confessed she was a thief. Since Penny claims she wants to reform, Walters releases her and sends her to live with Mrs. Kingdon. In spite of her teasing and taunts (or perhaps because of them), Walters finds himself falling in love with Penny.

TMDB Similar

The Ace of Cads

1926

An officer in the British Guards takes to drink when a friend and fellow officer convinces the woman they both love that he has another woman.

TMDB Similar

The New Teacher

1922

Society girl Constance Bailey becomes a schoolteacher in New York's Lower East Side, telling her fiancé, Bruce Van Griff, that she is sailing to Europe.

TMDB Similar

Her Summer Hero

1928

Champion college swimmer and summer lifeguard Ken Holmes saves Joan Stanton from drowning. They are sweethearts until a misunderstanding causes Joan to cast off Ken for his chief competitor, Herb Darrow. Joan promises Herb she will wear his fraternity pin if he wins the big swimming race at the hotel the next day. Despondent over his loss, Ken decides not to enter the race; later, he reconsiders when he learns that Joan is to wear Herb's pin if Herb wins. Ken wins the race and resolves his misunderstanding with Joan.

TMDB Similar

The Play Girl

1928

When Madge, a clerk in a flower shop, is sent to a bachelor's apartment to deliver and arrange a bouquet, she discovers a guest, young and handsome Bradley Lane, taking a bath. She loses her job and becomes a playgirl until Bradley, her true love, asks her to marry him.

TMDB Similar

Through the Wrong Door

1919

A young woman goes to visit friends but mistakenly rings at the wrong address. She is greeted and taken in out of the storm by a handsome young man to whom she is immediately attracted. What she does not know, however, is that this young man has been fleeced by her father and has sworn vengeance against him.

TMDB Recommended

Purgatory

1999

An outlaw band flees a posse and rides into Refuge, a small town where no one carries a gun, drinks, or swears. The town is actually Purgatory, and the peaceful inhabitants are all famous dead outlaws and criminals such as Doc Holiday and Wild Bill Hickok who must redeem themselves before gaining admittance to Heaven... or screw up and go to Hell.

TMDB Similar

Trilby and Little Billee

1896

Trilby lounges on a table with her shoes off, smoking, laughing, enjoying a piece of cake, and kissing her friend in a scene from the popular eponymous novel and stage play. Now lost, it is considered the first book-to-film adaptation.

TMDB Similar

Widow by Proxy

1919

Spinster sisters Sophronia and Angelica Pennington of Massachusetts refuse to meet Dolores, the bride of their nephew Jack, because she formerly was an actress. After Dolores receives word that Jack died at the front in France, she moves in with Gloria Grey, who barely supports herself by giving singing lessons. Soon Gloria's money dwindles and her creditors become threatening. When Dolores learns that she will inherit $5,000 from Jack's estate, she refuses to accept it out of pride, but Gloria convinces Dolores that they should go to Pennington Manor with their identities switched. Gloria impresses the aunts when she says that her godmother is a duchess. She and Jack's brother Steven fall in love, and when he is notified to report to naval duty, he proposes that they marry immediately. They then learn that Jack is alive. When Jack finds out that his wife was about to marry his brother, he starts to leave brokenhearted, but he sees the real Dolores and matters are straightened out.

TMDB Recommended

The Rainmaker

1956

Lizzie Curry is on the verge of becoming a hopeless old maid. Her wit and intelligence and skills as a homemaker can't make up for the fact that she's just plain plain! Even the town sheriff, File, for whom she harbors a secrect yen, won't take a chance --- until the town suffers a drought and into the lives of Lizzie and her brothers and father comes one Bill Starbuck ... profession: Rainmaker!

TMDB Recommended

Canyon Passage

1946

In 1850s Oregon, a businessman is torn between his love of two very different women and his loyalty to a compulsive gambler friend who goes over the line.

TMDB Recommended

The Bravados

1958

Jim Douglass arrives in the small town of Rio Arriba in order to witness the hanging of the four men he believes murdered his wife. When the convicts escape, Jim tracks them into Mexico, determined to see that justice is done. But the farther Jim goes in his quest for vengeance, the more merciless he becomes, losing himself in an unrelenting spiral of hatred and violence.

TMDB Recommended

Those Who Wish Me Dead

2021

A young boy finds himself pursued by two assassins in the Montana wilderness, with a survival expert determined to protect him, and a forest fire threatening to consume them all.

TMDB Recommended

The Warrior's Way

2010

A warrior-assassin is forced to hide in a small town in the American Badlands after refusing a mission.

TMDB Recommended

The Big Sky

1952

Two tough Kentucky mountaineers join a trading expedition from St. Louis up the Missouri River to trade whisky for furs with the Blackfoot Indians. They soon discover that there is much more than the elements to contend with.

TMDB Recommended

Ramrod

1947

A cattle-vs.-sheepman feud loses Connie Dickason her fiance, but gains her his ranch, which she determines to run alone in opposition to Frank Ivey, "boss" of the valley, whom her father Ben wanted her to marry. She hires recovering alcoholic Dave Nash as foreman and a crew of Ivey's enemies. Ivey fights back with violence and destruction, but Dave is determined to counter him legally... a feeling not shared by his associates. Connie's boast that, as a woman, she doesn't need guns proves justified, but plenty of gunplay results.

TMDB Recommended

Man Without a Star

1955

A wandering cowboy gets caught up in a range war.

TMDB Recommended

Davy Crockett, King of the Wild Frontier

1955

Legends (and myths) from the life of famed American frontiersman Davy Crockett are depicted in this feature film edited from television episodes. Crockett and his friend George Russel fight in the Creek Indian War. Then Crockett is elected to Congress and brings his rough-hewn ways to the House of Representatives. Finally, Crockett and Russell journey to Texas and the last stand at the Alamo.

What are the best movies like Sir Highwayman?

Penny of Top Hill Trail is the strongest current recommendation on this page for viewers looking for movies like Sir Highwayman.

How many recommendations are on the Sir Highwayman page?

This page currently lists 18 related titles for Sir Highwayman.

How often does the Movies Like Sir Highwayman page update?

This page refreshes whenever Movie Rankings rebuilds the related-title view for Sir Highwayman. It was last generated from site data on May 7, 2026.