Some people who see the show will probably raise the age-old objection to the spectacle of black male performers cross-dressing. The roster of comedy stars who have regularly done drag is almost a who’s who of top-grossing black comics: Flip Wilson, Tyler Perry, Martin Lawrence, Eddie Murphy. Black folks wary of mainstream — that is to say, predominantly white — tastes argue that white consumers are reveling in the degradation of black masculinity. In 2006, for example, Dave Chappelle insinuated, while speaking to Oprah Winfrey, that doing drag has negative effects on the black male image, and that white power brokers coerce these black stars into feminizing themselves all the way to the bank.

But seeing drag as fundamentally degrading is definitely close-minded, and possibly homophobic. Criticisms of this sort have never gotten any traction in the theater world, where eine kleine nachtemasculation might be just what the doctor ordered for macho cultures. If any misgivings about feminizing black men (or men of any color, really) were raised with Mitchell or Trask, they would voluptuously roll their eyes in response. These peacocks wouldn’t care if you put a sack of Idaho potatoes onstage in drag as long as it could sing.

A few days after our dinner, I caught up with Diggs at Soho House, a members-only club in the Meatpacking District to which he belongs. The dining room had the hushed elegance of a library, with windows overlooking the bustle of Ninth Avenue on a sunny Saturday late afternoon and an abundance of unfinished round wooden tables. Diggs is a regular here, and he seemed more relaxed, even though he had bitten his tongue during one of those eight-hour rehearsals. ‘‘It doesn’t hurt to talk,’’ he reassured me. Later I noticed a bright spot of blood in his mouth.

Upstairs, on the roof deck, dance music blasted and a crowd of half-naked sunbathers swarmed around a swimming pool like some MTV special on 30-somethings. People know Diggs here — a fit young woman with voluminous Beyoncé hair who used to date a friend came over to say hello; later, a pal with a bright gold grill covering his upper and lower front teeth sat down, describing himself as a ‘‘visual artist-slash-troublemaker.’’ Enthusiastic about the grill, Diggs said that he wanted one, too — ‘‘Some kind of a deal where it’s just one tooth.’’

Despite his image as a debonair race man, Diggs seems never to have gone through the requisite period of self-consciousness about macho posturing. Starring in “Rent” at 25 must have accelerated his evolution. He apparently doesn’t share any of Chappelle’s anxiety: For him, donning Hedwig’s wig seems to highlight a more personal transformation. Before divorcing, Diggs says, he clung to labels as keys to his identity — husband, father, actor, black, man. But afterward, everything changed — ‘‘aggressively, and in a fierce way.’’ Nevertheless, Diggs remains open to possibility. If you can credit Hedwig’s high-profile boundary-bashing with gaining more acceptance for L.G.B.T. people, surely the show can unbutton a heretofore strait-laced black actor’s image and open doors for everyone else.

The role of Hedwig is ‘‘everything I’ve ever wished for,’’ he said. Then he turned, in what seems unusual for him, ferocious: ‘‘This is me telling myself, ‘O.K., bitch, put your money where your mouth is. You’ve been telling agents and your best friends — I told Idina — ‘I want a chance to show everybody everything. I can dance and I can sing, and everybody knows I can act.’ ’’