20 Musicals From The 1920s [Movies & Theater]

11. The Drowsy Chaperone

The Drowsy Chaperone is a delightful and iconic musical set in the theater during the 1920s. It tells a story of an enthusiastic theater fan who, when feeling low, shares a long-playing record of his favorite music with his audience.

When playing the record, the guy makes witty observations about the music, script, and actors. The music is lively, with fabulous choreography and ribcracking comedy.

12. Nice Work If You Can Get It

This musical features popular George Gershwin songs, vibrant production numbers, romance, and humorous screenplay making fun of the prohibition era’s class snobbery. It follows two unlikely lovers trying to find true love in the prohibition era.

The musical won two Tony Awards and three Drama Desk Awards. George and Ira Gershwin wrote some of the most iconic jazz standards for this show, including “Someone to Watch Over Me,” “Sweet and Low Down,” “Fascinating Rhythm,” and “Let’s Call the Whole Thing Off.”

13. Singin’ in the Rain

Singin’ in the Rain is an iconic musical set in the 1920s, capturing the essence of Hollywood during the transition from silent films to “talkies.” The musical features some of the most memorable songs in musical theater history, such as “Good Mornin’,” “Make ‘Em Laugh,” and the title song, “Singin’ in the Rain.”

It follows a struggling Hollywood star Don Lockwood and his best friend, Cosmo Brown, who must navigate the changing times and their love lives.

14. Death Takes a Holiday

The theater musical follows a young nobleman, Prince Sirki, who takes a break from his job and takes a holiday in the human world.

When he meets a young woman named Grazia, who is about to be married off, he discovers the joys of life and love and ultimately learns to understand what life truly means.

The musical features a range of romantic ballads and musical numbers, including “Death is in the House,” “In the Middle of Your Life,” “Centuries,” “How Will I Know?” and “Nothing Happened.”

15. Bullets Over Broadway

The musical tells the story of a young playwright determined to make it big on Broadway and his producer, who’ll do anything to ensure the show opens successfully.

It’s full of witty dialogues and Broadway’s most memorable songs, such as “Runnin’ Wild” and “Finale (Yes, We Have no Bananas).” The production features stellar performances from a talented cast that brings the story to life. It’s sure to please theater enthusiasts and newcomers alike.

16. Bugsy Malone

Bugsy Malone is a gangster musical movie starring John Cassisi, Scott Baio, and Jodie Foster. Britain and America’s joint production features an all-child cast. It follows a gang of kids in Chicago and New York during the prohibition era led by Bugsy.

Bugsy dreams of becoming a big-time gangster, but his attempts don’t yield fruits. Along the way, he faces rival gangs and police corruption while trying to win the girl of his dreams.

The film features memorable songs such as “My Name Is Tallulah,” “So You Wanna Be a Boxer,” and “Ordinary Fool.” The soundtrack has been praised for its catchiness and has become a cult classic.

The musical was a commercial success and earned multiple award nominations. It has since gained a large following, and many consider it one of the most iconic musical films ever.

17. Mack & Mabel

As one of the best musicals from the 1920s, the musical is based on the real-life story of silent movie director Mack Sennett and his muse, actress Mabel Normand. The story focuses on their passionate, chaotic relationship that diminishes when their careers end with the transition from silent films to talkies.

Among the film’s best-known songs are the comedic “I Won’t Send Roses,” the wistful “Time Heals Everything,” and the sorrowful “Look What Happened to Mabel.”

Despite receiving Tony and Drama Desk Award nominations, Mack & Mabel didn’t attain sustainable success on Broadway. However, it has continued to enjoy popularity in concerts and staged performances since its premiere.

18. LoveMusik

The musical follows the lives and romantic entanglement of two renowned German composers, Kurt Weill and Lotte Lenya. The story begins with their initial encounter as desperate young musicians to when they became famous in Britain and the United States.

It incorporates some of the best songs, such as “I Do Not Love You,” “Surabaya Johnny,” and “Speak Low.” The production features performances from leads Michael Cerveris and Donna Murphy, who have won Tony Awards.

19. By Jeeves

The musical follows the story of Bertie Wooster, who’s a high-born halfwit, and his loyal servant, Jeeves. The two are always searching for adventure and getting themselves into compromising situations. Bertie is set to marry Madeline Bassett, a wealthy heiress with whom he shares no interests.

When his friend seeks help, he must find a way to make him attractive to Madeline Bassett. Jeeves is the right man for the job. The film features some of the best musical numbers, including:

• What Have You Got To Say, Jeeves
• Wooster Will Entertain You
• When Love Arrives

20. Floyd Collins

Set in the 1920s, the musical tells the story of Kentucky’s native, Floyd Collins, and his attempt to find fame and fortune. The musical follows Floyd’s journey as he discovers a cave on his family’s land and decides to turn it into a tourist attraction.

However, when Floyd gets trapped in the cave, a media frenzy arises as the nation watches and waits for his rescue.

It blends folk music and shows tunes, creating an exciting and uplifting atmosphere. Some of the most remarkable songs include “The Call,” “It Moves,” “Ballad of Floyd Collins,” and “Tween a Rock An’ a Hard Place.”

Best Musicals From The 1920s, Final Thoughts

The theater world underwent a significant transformation in the 1920s with the rise of musicals. The genre gained widespread popularity and continues to appeal to audiences today.

Listening to these incredible pieces is a beautiful way to appreciate the craft and talent that went into creating them. Whether comedy, drama, or romance, each musical represents music’s powerful impact on the theater. We hope you enjoyed reading our list of the best musicals from the 1920s.