Cumming's success in Cabaret led to the opportunity to star in a New York production of Sir Noël Coward's Design for Living, a play that he had long wanted to do. Critic Elysa Gardner praised Cumming's 2001 performance, writing that he "imbues Otto with a delightful mix of impishness and innocence."

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The following year, also in New York, he appeared in Elle, a short play by Jean Genet. The work had never been performed in English, and so Cumming wrote an adaptation based on a translation by Terri Gordon.

The simple premise of the play is that a young photographer is trying to take a perfect picture of the Pope for worldwide distribution. As New York Times critic Ben Brantley noted, however, "'Elle' is a dense, ornately verbal meditation on the tyranny of fame and manufactured images of glamour and authority."

The French feminine pronoun, elle, actually refers to the Pope since his title, Sa Sainteté ("His Holiness"), is a feminine noun; thus, the Pope is called "she."

Cumming gave a flamboyant performance as the pontiff. Brantley described his entrance as one "which for audacity and spectacle is unlikely to be topped . . . even by touring rock stars" with its special effects and Cumming's designer dress "that makes the most lavish Oscar-night gowns look modest." The reviewer went on to say that Cumming brought "miraculous new variety to the premise of the actor as war-weary whore that he perfected in 'Cabaret.'"

In addition to his work on stage, Cuming has appeared in dozens of films, in which he has shown remarkable versatility as an actor. His movies include light-hearted fare such as the three Spy Kids films (2001, 2002, and 2003, all directed by Robert Rodriguez) and the animated feature Garfield (2004, directed by Peter Hewitt), for which he did voice-overs. He has also appeared in adaptations of the works of Shakespeare--Titus (1999, directed by Julie Taymor), Charles Dickens--Nicholas Nickleby (2002, directed by Douglas McGrath), and Patricia Highsmith--Ripley Under Ground (2005, directed by Roger Spottiswoode).

With Jennifer Jason Leigh, who played Sally Bowles to his Emcee in the New York production of Cabaret, Cumming has co-written and co-directed a film, The Anniversary Party (2001). The two co-starred with a cast that included Gwyneth Paltrow (with whom Cumming had worked in Emma), Phoebe Cates, and John C. Reilly. The low-budget film, which was shot on digital video in only 19 days, was not a great commercial success but received favorable reviews. Critic Eric Harrison called it a "nicely acted and appealing drama" with "sterling performances" from the "marvelous cast."

Among Cumming's recent film projects are Lorena Machado's Bam Bam and Celeste (2005), starring Margaret Cho, and Sara Sugarman's Coming Out (planned for release in 2007), in which Cumming will play a gay cabaret performer who takes charge of a hapless Welsh rugby team after the death of his father, its coach. Cumming has also appeared on television in the lesbian soap opera, The L Word.

Cumming is the author of a novel, Tommy's Tale (2002), about a bisexual man who, as he approaches his thirtieth birthday, is both enjoying a freewheeling party scene and yearning for a more settled life as a father. The book received polite but unenthusiastic reviews.

In February 2005 Cumming introduced Cumming The Fragrance, which is called "beyond gender." Cosmetics International Cosmetic Products Report states that the "fusion of basic, masculine notes with adventurous ones . . . makes it original." A line of other body-care products is planned.

While pursuing his many projects, Cumming has still found time to work for worthy causes. He serves on the Board of Directors of Broadway Cares/Equity Fights AIDS and has taken part in many events on behalf of the organization. He is also a member of the Board of Advocates of the Planned Parenthood Federation of America, the Ambassadors Committee of Free Arts for Abused Children NYC, and the Honorary Advisory Board of Living Beyond Belief, an organization that encourages New York City high school students to become active in the fight against AIDS.

In addition, he participates in numerous events for Bailey House, a New York organization that provides housing and other important services to people with HIV/AIDS. He has also done a comedy benefit for Beverly Hills's Trevor Project, whose goal is to promote tolerance for glbtq teens and whose national Trevor Helpline (866.4.U.TREVOR) provides round-the-clock suicide prevention services. He also served as the Celebrity Grand Marshal of the 2004 San Francisco LGBT Pride Parade.