Chenoweth made her Broadway debut in the musical Steel Pier. With a score by John Kander and Fred Ebb and a book by David Thompson, it opened April 24, 1997, at the Richard Rodgers Theatre. Directed by Scott Ellis and choreographed by Susan Stroman, the cast featured Karen Ziemba as Rita Racine, Daniel McDonald as Bill Kelly, Debra Monk as Shelby Stevens and Gregory Harrison as Mick Hamilton.
The New York Times' Ben Brantley gave the show a mixed review. "Yet despite the flashes of grace and inventiveness in Ms. Stroman's choreography and the modest melodic appeal of the work's songs," he wrote, "Steel Pier is insulated by a fuzzy cover of blandness."
The production was nominated for 11 Tony Awards, but won none, and closed after 76 performances. Chenoweth received a Theatre World Award for her role as Precious McGuire.
Chenoweth's next Broadway role came in the 1999 revival of You're a Good Man, Charlie Brown. She played Sally Brown in a cast that included Roger Bart as Snoopy, Anthony Rapp as Charlie Brown and BD Wong as Linus.
The musical opened at the Ambassador Theatre Feb. 4, 1999. Critics raved about Chenoweth's portrayal of Sally; the New York Times' Ben Brantley claimed she gave "one of those break-out performances that send careers skyward" and was "the only significant reason for adults unaccompanied by children to sit through this mild-mannered, sticky evening of skits and songs."
Chenoweth received the 1999 Tony Award for Best Featured Actress in a Musical for her work. Other accolades included a Drama Desk Award and a Clarence Derwent Award for Most Promising Female Performer.
After appearing in the short-lived comedy Epic Proportions, Chenoweth originated the role of Glinda in the megahit musical Wicked. She starred opposite Idina Menzel as Elphaba, Joel Grey as the Wonderful Wizard of Oz, Carole Shelley as Madame Morrible and Norbert Leo Butz as Fiyero.
Directed by Joe Mantello, the production opened Oct. 30, 2003, at the Gershwin Theatre. In his review for the New York Times, Ben Brantley called the production "bloated" and a "Technicolorized sermon of a musical," but praised Chenoweth's work. He wrote: "But for aficionados of the American musical, it's Ms. Chenoweth who's the real thing, melding decades of performing traditions into something shiny and new. Wicked does not, alas, speak hopefully for the future of the Broadway musical. Ms. Chenoweth, on the other hand, definitely does."
Chenoweth received a Tony nomination for her performance, but lost to costar Menzel. Despite the initial negative response from critics, Wicked celebrated its tenth anniversary on Broadway last year and is currently the 11th longest-running show in Broadway history.
In 2006 Chenoweth starred alongside Brian d'Arcy James and Marc Kudisch in a revival of Jerry Bock and Sheldon Harnick's The Apple Tree, a series of three one-act musicals based on stories by Mark Twain, Frank R. Stockton and Jules Feiffer. The musical opened Dec. 14, 2006, at Studio 54.
Once again, the general consensus from critics was that Chenoweth's performance was the highlight of an otherwise lackluster production. Variety's David Rooney wrote: "Chenoweth has the timing and physical comedy skills of a classic screwball star like Carole Lombard, and her airy, effortless soprano makes enchanting work of songs such as 'Here in Eden'...but even with her delectable turn, the material is too thin to support an entire act."
The revival ran for 99 performances before closing March 11, 2007.