This musical has a long and complicated history. It began as a New York workshop in October 1999 under the title “Wise Guys” with Nathan Lane and Victor Garber, directed by Sam Mendes. A legal case involving producer Scott Rudin and Weidman and Sondheim held up further production. With major re-writing, the new version opened in Chicago in June 2003, directed by Harold Prince, and re-titled “Bounce”. This version received poor notices and closed after playing Washington in November 2003.
A third version was created - this time running just 90 minutes without an interval - and, under its new name, “Road Show”, it opened off-Broadway on November 18th 2008 (previews from October 28th) and closed on
December 28th. This third version was directed by John Doyle and won the 2009 Obie Award for Music & Lyrics, and the Drama Desk Award for Lyrics.
After the death of Addison Mizner, people who knew him, including his estranged lover Hollis Bessemer, comment on his life and the way he squandered his talents ("Waste"). Addison's brother Wilson appears and speaks to Addison, who angrily claims that Wilson was the cause of all his failures. Wilson brushes off Addison's anger and reminds him of the days when they were a team. The time shifts to Papa Mizner's death at the beginning of the 20th century. On his deathbed, Papa Mizner charges his sons with the task of using their gifts to shape America ("It's In Your Hands Now"), telling them that there's a "road" for them to follow. Mama Mizner tells the brothers that their family's wealth has been eaten away by Papa's long illness and advises them to seek gold in Alaska; Addison is reluctant, but goes along with Wilson anyway ("Gold!").
In Alaska, the brothers share a sleeping bag and reminisce about their childhood ("Brotherly Love"). Wilson leaves to get supplies while Addison works the claim; away from Addison, Wilson is lured into a game of poker, which he is initially bad at but masters quickly. Addison comes to find him, and is shocked to discover that his brother has become a gambler. Wilson tries to explain his newfound love of taking risks regardless of what's at stake ("The Game"), and Addison is almost convinced, but when Wilson stakes their gold claim in a poker game and wins the saloon in which the game is taking place, the shade of Papa Mizner appears and tells Addison that this was not what he had in mind for his sons.
Addison leaves in disgust with his share of Wilson's winnings and travels around the world searching for business opportunities and a sense of purpose ("Addison's Trip"). All of his ventures fail due to bad luck, and he is left with nothing but a collection of souvenirs—but the souvenirs inspire him to take up architecture (so that he can design a house in which to show them off). Meanwhile, Wilson's businesses in Alaska have failed, and he comes south in the hopes of getting help from Addison. Addison has only just begun to practice as an architect, and Wilson seduces and marries his first client, a rich widow, and fritters away her money on various flashy endeavours, including promoting fixed boxing matches and horse races ("That Was A Year"). Although Wilson's various partners lose out by being associated with him, they remain fond of him because of the verve and energy with which he lives. Even Mama Mizner, who is being looked after by Addison and never receives any visits from Wilson, enjoys reading about Wilson's exploits, saying that she can live through him ("Isn't He Something!"). Only Addison remains uncharmed by Wilson, and when Wilson finally comes back, his resources exhausted, intending to ask Addison for help, he finds that Mama has died in his absence. Addison angrily throws Wilson out of the house.
Later, there is a land boom in Florida ("Land Boom!"). Addison decides to travel to Palm Beach to take advantage of the many rich people settling there who will be needing to have houses built. On the train he meets Hollis Bessemer, with whom he is instantly smitten. Hollis explains his situation: he is the son of a wealthy industrialist, but he has been cut off by his father for refusing to enter the family business. His real passion is art, and although he is not himself talented enough to become an artist, he dreams of creating an artists' colony in Palm Beach with the help of his aunt, who is staying there in a hotel ("Talent").
Hollis and Addison arrive at Palm Beach, and Addison shows Hollis's aunt a plan for a house he proposes to build for her. Impressed, she agrees and offers to sponsor Hollis's artists' colony. However, Hollis and Addison, now lovers, are too busy designing resort homes for the rich ("You") and enjoying each other's company ("The Best Thing That Ever Has Happened") to follow up on Hollis's original plan—until Wilson arrives at Hollis and Addison's house, destitute and sick ("The Game [Reprise]"). Addison reluctantly takes him in, and when Wilson has recovered he begins to work on Hollis, persuading him to be a patron to his newest scheme: to build a brand-new city in Boca Raton with Wilson as promoter and Addison as chief architect ("Addison's City").
But Wilson's conman instincts resurge, and he promotes the Boca Raton real estate scheme with increasingly extravagant and eventually fraudulent claims, creating a price bubble ("Boca Raton"). Addison goes along with this, and it is Hollis who finally puts a stop to both the real estate scheme. He asks Addison choose between him and Willie, and Addison, brought to a state of desperation by all that has happened, drives Hollis away by telling him that he had never loved him. Addison tells Wilson to get out of his life ("Get Out"), but Wilson responds by saying that Addison doesn't actually want Wilson to go because he loves him too much ("Go"). Addison admits that he does love Wilson, but he still wants him to go. Wilson finally leaves for good.
But not quite, for in the finale (returning to the first scene) all the characters leave the stage except for Wilson and Addison, and Wilson realises that he, too, has died. They bicker halfheartedly but their differences no longer mattering enough to keep them apart. Confronted by their father, they shrug off his criticisms and the brothers set out together on the road to eternity—or, as Wilson calls it, "the greatest opportunity of all." "Sooner or later," he says "We're bound to get it right."