Cumming made a noteworthy Broadway debut as the Emcee in the 1998 revival of John Kander and Fred Ebb's Cabaret. He starred opposite Natasha Richardson as Sally Bowles, Ron Rifkin as Herr Schultz and John Benjamin Hickey as Clifford Bradshaw. The production opened March 19, 1998, at the newly christened Kit Kat Klub, located in what was previously known as the Henry Miller's Theatre.

The revival received ten Tony Award nominations and won four, including Best Revival of a Musical and Best Actor in a Musical for Cumming, who also won Drama Desk, Outer Critics Circle and Theatre World Awards for his potraryal of the Emcee. The musical went on to play 2,377 performances and remains the third longest-running revival in Broadway history, after Oh! Calcutta! and Chicago.

Read the Cabaret Playbill here.

Cumming next appeared on Broadway in a revival of Design for Living, Noël Coward's dark comedy concerning a ménage à trois. Jennifer Ehle and Dominic West also starred.

The play opened at the American Airlines Theatre March 15, 2001, to less than stellar reviews. The New York Times' Ben Brantley wrote: "Any production that features Mr. Cumming, who found fame brilliantly reinventing the decadent M.C. of Cabaret, would automatically seem to have a leg up in satyr appeal. Yet earnestness trumps sexiness again and again in this Design, which has been directed with an uncharacteristically slow and shaky hand by Joe Mantello."

The production ran for a limited engagement of 69 performances before closing on May 13, 2001.

Read the Design for Living Stagebill here.

In 2006, Cumming played Macheath (Mack the Knife) in Roundabout's revival of Bertolt Brecht and Kurt Weill's The Threepenny Opera. Scott Elliott directed a cast that included Cyndi Lauper, Jim Dale, Nellie McKay and Ana Gasteyer.

The production opened April 20, 2006, at Studio 54, where it ran for 77 performances. In his New York Times review, Ben Brantley noted that "Mr. Cumming brings much conviction and agony to Macheath's songs of the oppressed." The show received two Tony Award nominations, one for featured actor Dale and one for Best Revival of a Musical.

Read the Threepenny Opera Playbill here.

Cumming's next Broadway role was in the National Theatre of Scotland production of William Shakespeare's Macbeth. He played the title character as well as all of the other significant characters in this one-man adaptation, which opened April 21, 2013, at the Ethel Barrymore Theatre.

New York Magazine described Cumming as "tireless and brave in enacting a difficult story," and the New York Times wrote that his "energetic flitting among characters keep us constantly entertained." The play ran for a limited engagement of 73 performances.

Read the Macbeth Playbill here.