The musical opened October 16, 1997, on Broadway; Robert Longbottom directed and choreographed, and the cast starred Emily Skinner as Daisy and Alice Ripley as Violet.

The Boss, the ringmaster of a sideshow, introduces the exhibits: the bearded lady, a geek, the Cannibal King, the seraglio of a Hashemite sheik, and, lastly, his star attraction, the Siamese twins ("Come Look at the Freaks").

Buddy Foster, an aspiring musician, brings Terry Connor, a press agent and talent scout for the Orpheum Circuit, to see the Siamese twins, persuading him to enter the show all the way.

Daisy, Violet and Jake, whom Terry has invited to help backstage on the twins' tour, bid farewell to their sideshow family ("Say Goodbye to the Freak Show").

The second act opens with the Hilton Sisters at the height of their success - a Follies-style production number ("Rare Songbirds on Display").

Robert Longbottom directed and choreographed, the sets were by Robin Wagner, costumes by Gregg Barnes and lighting by Brian MacDevitt.

[4] In 1998, TheatreWorks near San Francisco produced the regional premiere of Side Show at the Mountain View Center for the Performing Arts.

The cast also included Debra Wiseman (Bullets Over Broadway, The Scarlet Pimpernel) as Violet, AJ Vincent (The Will Rogers Follies) as Terry (Dean Goodman Critics Choice Award Best Actor in a Musical), Pierce Peter Brandt (Les Miserables, Martin Guerre) as Buddy, and Stephonne Smith (The Scarlet Pimpernel) as Jake.

In 2001, Signature Theatre Company's production starred Amy Goldberger (Daisy), Sherri Edelen (Violet), Will Gartshore (Buddy Foster), Matt Bogart (Terry Connor), Eric Jordan Young (Jake), and Michael Sharp (The Boss).

[6] An abridged version of Side Show was presented at the Kennedy Center in Washington, D.C. October 2–5, 2008 as part of their Broadway: Three Generations production.

The show had a "darker approach" and "incorporates new songs as well as additional biographical details of the Hilton twins' life and historical figures of the era.

Several other songs from the original were cut: "You Deserve a Better Life", "Crazy, Deaf and Blind", "More Than We Bargained For", "When I'm By Your Side", "Overnight Sensation", "We Share Everything", "Rare Songbirds on Display", and "Beautiful Day for a Wedding".

The production next played at the Kennedy Center in June and July 2014. with choreography by Anthony Van Laast, scenic design by David Rockwell, costumes by Paul Tazewell, lighting by Jules Fisher and Peggy Eisenhauer and sound by Kai Harada.

The cast starred Davie and Padgett and also featured Matthew Hydzik as Buddy Foster, Robert Joy as Sir, Ryan Silverman as Terry Connor and David St. Louis as Jake.

[11] Directed by Hannah Chissick, the cast featured Louise Dearman (Daisy) and Laura Pitt-Pulford (Violet), with Dominic Hodson as Buddy Foster.

[12][13] On March 3rd 2024, a concert production was staged at The London Palladium, starring Louise Dearman (Daisy) and Rachel Tucker (Violet).

The first collegiate production of the reworked version of Side Show was directed by VP Boyle and produced as an immersive theatrical experience by USC School of Dramatic Arts in October, 2016[14] and featured real twins.