The Civil War is not so much a traditional book musical as it is a free-form musical extravaganza intended to take advantage of the unique talents of composer Frank Wildhorn. The show incorporates letters, diaries, historical documents and Walt Whitman's poetry as it explores the brutal civil war that claimed the lives of 620,000 Americans. Following events from the beginnings of the war at Fort Sumpter all the way to its bloody conclusion, The Civil War focuses not only on issues of the unity of the nation and the abolition of slavery, but also on the impact of the war on individual families. The score includes a number of brilliant songs including "Sons of Dixie" in which young recruits, expecting a quick victory, look forward to parades in their honor and the admiration of women. Other memorable numbers include "Tell My Father" in which a dead soldier sings to his brother who is fighting on the opposite side and "Judgement Day" in which two captains question whether they are doing the right thing.

The Civil War opened at the St. James Theatre on April 22, 1999, with a cast that included Michel Bell (Clayton Toler), Matt Bogart (Private Sam Taylor), Leo Burmester (Autolycus Fell), Gilles Chiasson (Corporal William McEwen), Lawrence Clayton (Benjamin Reynolds), Mave Clemmons (Sergeant Virgil Frank/Auctioneer's Assistant), Mike Eldred (Corporal John Beauregard), Cheryl Freeman (Bessie Toler), Anthony Galde (Private Darius Barksdale), Hope Harris (Violet/Nurse), Capathia Jenkins (Harriet Jackson), Keith Byron Kirk (Frederick Douglas), Michael Lang (Captain Emmett Lochran), Beth Leavel (Mabel/Mrs. Bixby), David M. Lutken (Corporal Henry Stewart), Gene Miller (Captain Billy Pierce), Irene Molloy (Sarah McEwen), Wayne Pretlow (Exter Thomas), Jim Price (Private Cyrus Stevens), John Sawyer (Private Nathaniel Taylor), Ron Sharpe (Private Conrad Bock), Bart Shatto (Private Elmore Hotchkiss), Rod Weber (Sergeant Patrick Anderson), and Cassandra White (Liza Hughes). The show went on to earn a number of awards including Tony nominations for "Best Musical" and "Best Original Score", five Drama Desk nominations including "Outstanding Musical", two Outer Critics Circle Awards including "Outstanding Featured Actor in a Musical" (Michel Bell), and a Drama League nomination for "Distinguished Production of a Musical" The production closed on June 13, 1999.

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