I know it hasn't happened before, and the only circumstances I can think of of an actor returning to their Tony Winning Role are Ethel Merman, Carol Channing, Yul Brenner, and now Alan Cumming. Would it be possible for Cumming to be nominated and win the Tony for the Emcee, a role he already won a Tony for?
Not unless it's the same part in a different play/show. Example: If Peter O'Toole had played Henry II on Broadway in both Becket and Lion in Winter he could have been tony-nominated for both (he was oscar nominated for playing Henry in the films of both). In addition, the two parts of Angels in America, which opened in different seasons, were considered two separate plays for purposes of winning tony's both for the play (twice) and for Stephen Spinella (twice, one as featured, once as lead, playing the same role, Prior Walter, in both).
What if it's the same part in a different conception or version of the same show? For example, what if the new Cabaret revival were using the book, score, and ideas of the original production and not the Mendes revival? In that case, could Cumming be nominated again not for *recreating* the role, but for playing the same role in a markedly different production?
The textbook example here is Lonette McKee. She was nominated in 1983 for her performance as Julie in the Houston Grand Opera's Show Boat. She played the role again in the Garth Drabinsky/Hal Prince Show Boat in 1994, but even though that production was completely different from the 1983 production, Tony Administration ruled that she could not be nominated again for playing Julie. (I think it was the wrong decision, since the productions were different).
Begin at the beginning and go on till you come to the end: then stop.
Lonette McKee was nominated for her turn as Julie in the Huston Grand Opera production of SHOW BOAT in 80's and was therefore deemed ineligible for the Hal Prince production in the 90's.
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