A drag show is a form of entertainment performed by drag artists impersonating men or women, typically in a bar or nightclub as a burlesque-style, adult-themed nightclub event.

The modern drag show originated in the speakeasies and underground bars of 1920s and 1930s Prohibition America, in what was known as the Pansy Craze. Drag became a part of gay culture and a form of entertainment usually enjoyed by adults in bars.

Typically, a drag show involves performers singing or lip-synching to songs while performing a pre-planned pantomime or dancing. There might also be some comedy, skits, and audience interaction. The performers are often given cash tips by the audience members. The performers often don elaborate costumes and makeup, and sometimes dress to imitate various famous opposite sex singers or personalities. Young male dancers have often been included. Some other events are centered around drag-show type entertainment, such as Southern Decadence where the majority of festivities are led by the Grand Marshals, who traditionally are drag queens.

The first known drag balls in the United States were in Harlem in the 1920s, at the Rockland Palace. These shows featured extravagant performances of gays and lesbians impersonating the opposite sex and competing against one another in fashion shows. Harlem drag balls were primarily made up of people of color. White people were not excluded but did not typically participate. Drag balls were social events that brought people together who were on the margins of society and they often had to meet in secret.

During World War II, parody drag shows were also a regular kind of entertainment for soldiers who dressed up as humorous-looking women and put on shows for each other.

Doc Benner, and Danny Brown produced the show which started in Miami, Florida, at a gay bar known as Club Jewel Box. This show would go on to set the stage for the touring drag show known as the Jewel Box Revue. The Jewel Box Revue was the longest running drag show that performed from the 1940s until the 1970s across the United States. They had at least ten specific performances in their repertoire, which was helpful for shows that ran for longer periods of time at the same place. The show had their own music and dances that were composed and choreographed for performers, they also did comedy sketches and some stand-up performances. The revue was made up of a diverse group that included African Americans, Latinos, Native Americans, and whites, which was unusual for the times before the Civil Rights Movement.

From 1955 to 1969 the Master of Ceremonies and only drag king of the revue was biracial, butch lesbian Stormé DeLarverie, whose June, 1969 scuffle with police was, according to DeLarverie and many eyewitnesses, the spark that ignited the Stonewall uprising in New York City's Greenwich Village.

Many of the venues they performed at were part of the "chitlin' circuit", the Howard Theatre (Washington, D.C.), the Baltimore-Royal Theatre, Uptown Theatre (Philadelphia) and the Regal Theater in Chicago. In 1959 they began performing at The Apollo Theater in New York City and it was always a full house when they came to town.