Act One

The curtain rises as the show begins with a vocal overture. The cast appears on stage throughout the overture, highlighting some of the greatest hits by Mr. Stephen Sondheim.

A video of Stephen Sondheim comes on. He introduces himself to the audience and reveals why he was named Stephen, discusses his birth and then introduced his father; a self-taught piano player who helped Stephen learn the ropes and write his very first tune, "I'll Meet You at the Donut." The cast performs the song.

Sondheim then introduces A Funny Thing Happened on the Way to the Forum, the first musical for which he wrote both the music and lyrics. He explains that it is based on an idea by a man named Burt Shevelove. The cast performs "Invocation / Forget War." Sondheim adds that the song was the original opening but was cut when director, George Abbott, said that he did not like it. In its place came "Love Is in the Air." The cast proceeds to perform the song.

Sondheim goes on to say how much of a "disaster" the show was. To attempt to solve the problem, Jerry Robbins joined the team as a show doctor; he tells Stephen to write a new opening. In turn, Stephen writes "Comedy Tonight." The cast appears on stage to perform the well-known tune.

We now transition to Sondheim's childhood; an actress performs "Take Me to the World." The video begins again, with Stephen discussing his parent's divorce and his move to Pennsylvania with his mother. He goes on to explain how Dorothy and Oscar Hammerstein became his surrogate parents during his teen years, and that this is why he became a songwriter... because Oscar was.

Moving into the early career of Stephen Sondheim, a video comes on. It is Stephen, discussing his first professional show at the age of 23 years old, called Saturday Night. He goes on to explain that Lem Ayers, the lead producer of the show, died about halfway into the process. The cast appears and they perform "So Many People," a song from the show.

After trying to pitch the music of Saturday Night to producers, he became noticed and was invited to do the lyrics for West Side Story. Sondheim admits that he was very hesitant initially, but Hammerstein encouraged him to take the job. The cast performs "Something's Coming."

An interview between Mike Douglas and Sondheim pops up, where they are discussing neurotic characters. Sondheim reveals that he likes neurotic people. A man and a woman perform "You Could Drive a Person Crazy," from Sondheim's Company. "The Wedding Is Off," an old version of "Getting Married Today," is then performed. Next, we are treated to a rendition of "Now You Know," from Merrily We Roll Along.

A video of Sondheim begins, introducing his relationship with longtime collaborator, Hal Prince, as a producer and director. It then segues into "Franklin Shepard, Inc.," a song about a writing partnership gone bad, from his musical, Merrily We Roll Along. Immediately following, an actor appears on stage and performs the ballad "Good Thing Going."

Sondheim begins discussing his writing process. He mentions the difficulty of getting those first words down and, furthermore, the challenge of completing a song once the shape of it has completely changed. "Waiting for the Girls Upstairs," from the iconic musical, Follies, is played out on the stage. Sondheim notes that this octet was originally intended as a duet.

Next, we transition to the story of Sweeney Todd, and how it all came to be. Sondheim mentions that he saw the play, written by Christopher Bond, in a small theatre outside of London and immediately thought it could be a great musical. "Epiphany," from Sweeney Todd, is performed as Sondheim explains the drastic mood changes within the song; it's about a man whose mind is cracking.

At the conclusion, a new video begins. In it, Sondheim talks about the inspiration behind Passion; a song from the show, "Fosca's Entrance (I Read)," is presented. Sondheim adds more about the development of the story and the characters as we are treated to a new song from the musical: "Is This What You Call Love?" Sondheim then introduces the song, "Loving You," which was added during previews in an attempt to explain the obsession on the part of the ugly woman.

The interview with Mike Douglas comes on again, with Sondheim mentioning his "surprise hit," as we see a compilation of spliced-together videos that create an entire performance of "Send in the Clowns" from A Little Night Music. It is a YouTube montage.

Next comes the topic of relationships. Stephen Sondheim discusses his confusion with sexuality, and that he once visited a Freudian analyst, admitting that he didn't fall in love until the age of 60. The cast performs a rendition of "Happiness" from Passion.

Act One ends with a finale medley, including "Ever After" from Into the Woods, "A Weekend in the Country" from A Little Night Music and "Sunday" from Sunday in the Park with George.

Act Two

The second act opens with Sondheim discussing the environment in which he writes, and the cast performing an original tongue-in-cheek Sondheim song titled "God."

We now transition to love songs from a "60 Minutes" interview. Sondheim explains that he needs characterizations, or a topic, in order to begin writing a love song. He cannot freely write a generic love (or "torch") song. Two women come to the stage and perform "Losing My Mind / Not a Day Goes By."

Sondheim is now discussing the question of his songs being autobiographical. He insists that none of the characters are him; they are new people, created with the help of his collaborators. He adds that there is only one autobiographical song that he has written.  A trio of actors appears and performs "Opening Doors" from Merrily We Roll Along.

Next, he mentions the creation of a show called Bounce (now known as Road Show). The cast performs a song from the musical titled "The Best Thing That Ever Has Happened."

A new video begins; Sondheim is discussing the origins of Company and how marriages are. He reveals that he took out a notepad, called Mary Rodgers, and began a long discussion with many notes. Sondheim then goes on to explain that there were three endings to the musical – the first involved a proposal from Bobby to a girl named Amy. The song was called "Multitudes of Amys." Sondheim then notes that they changed it to end with a song, by Bobby, assessing all of the marriages. This song was titled "Happily Ever After." He says that the producers thought it was too much of a downer, so he turned that song into the final ending: "Being Alive."

We transition to the issue of poetry versus lyrics. Sondheim is discussing changes he made in the London revival of Follies and why he made them. "Ah, But Underneath" is performed. A clip from the Levin Interviews plays; Sondheim tries to define the difference between poetry versus lyrics and what he writes: poetic lyrics. A woman appears on stage and sings "In Buddy's Ears" from Follies.

Sondheim comes onto the screen again and proclaims that Assassins is the show with which he ever came the closest to being satisfied... because he cannot think of any way to fix it. The cast performs "Something Just Broke." This transitions into "The Gun Song."

We now begin finding out more about the shows on which Sondheim collaborated as a contributor, both as a lyricist and composer. The first addressed is Do I Hear a Waltz?, in which Sondheim wonders why he spent a year and a half working on it. The cast performs the title song. The next collaboration mentioned is Gypsy, and Sondheim reveals a song that was intended for Rose, but cut from the second act after only a single performance, called "Smile, Girls." He then proceeds to relay his favorite Ethel Merman story that involves "The Loretta Young Show."

Sondheim now begins talking about the show that is "closest to his heart," which is Sunday in the Park with George. The song, "Finishing the Hat," is performed. It is followed by the song, "Beautiful."

Discussing mothers and children, Sondheim reveals that he had a difficult relationship with his mom and feels that she never wanted him. The cast performs "Children Will Listen" from Into the Woods. An interview is played, and Sondheim admits to regretting not having, children but insists that teaching his art is another way to do that. An actress sings "Send in the Clowns" from A Little Night Music.

The show ends with a section about the role of collaborators and how they have had an impact on Sondheim as a person and a writer. The cast closes with various tunes from Sondheim favorites, including: Company, Merrily We Roll Along and Anyone Can Whistle.