Best Harold Lloyd Movies

Harold Lloyd’s career has left an indelible mark on comedy and film for generations. From his captivating silent films to his later talkies, the more one watches Lloyd’s movies, the more they appreciate his talent as an actor, director, writer, producer, and comedian. To that end, it is no wonder Lloyd’s films have become so beloved by today’s audiences.

To ensure you don’t miss out on the best of Harold Lloyd’s work, I have compiled a list of our favorite films from his impressive body of work, taking into consideration ratings across social movie sites such as IMDB and Letterboxd. Whether you’re looking for your first taste of silent cinema or simply want to revisit some of Lloyd’s best-loved moves, this should serve as a handy guide!

The Most Popular Harold Lloyd Movies Today

1. Safety Last! (1923)

• Genre: Action / Thriller / Comedy
• Starring: Harold Lloyd, Mildred Davis, Bill Strother, Noah Young
• Directed by: Fred C. Newmeyer, Sam Taylor

Safety Last! is the most popular Harold Lloyd movie today — and for good reason. This silent comedy has one of the most iconic scenes in all of silent movie history: the scene where Lloyd is clutching a clock and dangling over city traffic below. Highly enjoyable to watch, this movie also remains one of the best movies of all time and is a part of the Criterion Collection (spine #662)!

In Safety Last, Lloyd plays a small-town man who moves to New York City to make it big and impress his girlfriend (Davis). However, he soon finds out how hard it is to make it in the city and earn money… and this leads him to perform one crazy stunt after the other.

2. The Freshman (1925)

• Genre: Romance / Comedy
• Starring: Harold Lloyd, Jobyna Ralston, Brooks Benedict, James H. Anderson
• Directed by: Fred C. Newmeyer, Sam Taylor

The Freshman is also one of the most popular Harold Lloyd movies today and is one of the films he’s best remembered for. Just as with Safety Last!, The Freshman is considered one of the best comedies ever made and is also a part of the Criterion Collection (spine #703)!

The Freshman was Lloyd’s biggest blockbuster when it was released, and the movie still stands up almost 100 years later. In this comedy, Lloyd plays a new college student who joins the football team after making a fool of himself, all on his quest to make friends. Truly a must-watch film.

3. The Kid Brother (1927)

• Genre: Comedy / Drama
• Starring: Harold Lloyd, Jobyna Ralston, Walter James, Leo Willis
• Directed by: Ted Wilde

The Kid Brother stars Lloyd as the feeble brother of a brawny family who tries to prove that he, too, can be strong and help the family. A wonderful Lloyd movie, this silent western comedy is full of action and romance — and maybe Lloyd’s best overall film because of the blending of genres, as well as the excellent, engaging story.

Much like the other silent films earlier on this list, The Kid Brother is considered one of the best silent comedies ever made and is a part of the Criterion Collection (spine #964)!

4. Speedy (1928)

• Genre: Action / Comedy
• Starring: Harold Lloyd, Ann Christy, Bert Woodruff, Babe Ruth
• Directed by: Ted Wilde

Yet again, we’ve got another excellent Harold Lloyd movie. Speedy, which is in many ways a love letter to New York, features excellent stunts and Lloyd in one of his best performances. This film also happens to be Lloyd’s last silent film.

In Speedy, Lloyd plays a scatterbrained New Yorker, and diehard Yankees fan, who can’t seem to keep a job. He decides to help his sweetheart’s grandfather with his horse-drawn streetcar business, the last in the city, and a lot of chaos ensues. Truly a wonderful film — and a part of the Criterion Collection (spine #788)!

5. Girl Shy (1924)

• Genre: Romance / Comedy
• Starring: Harold Lloyd, Jobyna Ralston, Richard Daniels, Carlton Griffin
• Directed by: Fred C. Newmeyer, Sam Taylor

Girl Shy is an amazing silent romantic comedy that also happens to be one of the most popular Harold Lloyd movies today. Just like every Lloyd movie, this film is pure entertainment. Here, he plays a shy man from a small town who heads to the city to become a published author and find love along the way — though he faces many obstacles!

6. Grandma’s Boy (1922)

• Genre: Comedy
• Starring: Harold Lloyd, Mildred Davis, Anna Townsend, Charles Stevenson
• Directed by: Fred C. Newmeyer

In Grandma’s Boy, Lloyd plays a timid young man who sits out a townwide search for a local murderer. However, when his grandmother tells him a story and gives him a talisman that supposedly helps mere men become brave heroes, he decides to act out — and it’s a delight to watch.

7. Why Worry? (1923)

• Genre: Adventure / Comedy
• Starring: Harold Lloyd, Jobyna Ralston, John Aasen, Wally Howe
• Directed by: Fred C. Newmeyer, Sam Taylor

Why Worry? is also one of the most popular Harold Lloyd movies today. It’s also quite fun to watch, as all Lloyd silent comedies are! In Why Worry?, Lloyd plays a rich man who heads to South America to try to get over his many sicknesses and illnesses — and then finds himself stuck in the middle of a revolution.

8. For Heaven’s Sake (1926)

• Genre: Action / Romance / Comedy
• Starring: Harold Lloyd, Jobyna Ralston, Noah Young, Jim Mason
• Directed by: Sam Taylor

For Heaven’s Sake was one of the most popular Harold Lloyd movies when it was first released — and it’s also one of the most popular Lloyd movies today. It’s a delightful slapstick comedy that has stood the test of time! In this film, Lloyd plays a rich ladies’ man who ends up falling in love with a priest’s daughter and changes his personality as a result.

9. The Milky Way (1936)

• Genre: Comedy
• Starring: Harold Lloyd, Adolphe Menjou, Verree Teasdale, Helen Mack
• Directed by: Leo McCarey

The Milky Way is the first Lloyd talkie on this list, as Lloyd is best remembered for his silent films today. However, when The Milky Way was released in 1936, it was a box office hit and is the most successful Lloyd talkie released. It’s a great comedy!

In The Milky Way, Lloyd plays a milkman who knocks out a boxer by mistake, and then finds himself gaining an interesting new career in the boxing ring.

10. The Sin of Harold Diddlebock (1947)

• Genre: Comedy
• Starring: Harold Lloyd, Frances Ramsden, Jimmy Conlin, Raymond Walburn
• Directed by: Preston Sturges

The Sin of Harold Diddlebock isn’t the best Harold Lloyd movie, but it is notable for many reasons. The iconic Preston Sturges directed this comedy, a film that is a continuation of The Freshman. This 1947 was also Lloyd’s last feature film he ever starred in.

In The Sin of Harold Diddlebock, Lloyd plays an unmarried, unemployed man with barely any money who goes out on the town after he loses his job — and ends up being knocked out by a powerful drink a bartender gives him. A lot of chaos ensues after this — and it is quite fun to watch!