In just the second time the award for Best Actor in a Musical (1949) was awarded to Ray Bolger, who donned a dress for part of his performance in Where's Charley? (Raul Julia was nominated for the same role in the 1975 revival.) Interestingly, the second time the award for Best Featured Actor in a Musical (1950) was awarded to Myron McCormick for his hilarious turn as Luther Billis in South Pacific. In that show, he was Mary Martin's "Honey Bun." In that same number, Ms. Martin, Best Actress in a Musical, was dressed as a seabee!
MARY MARTIN, MYRON MCCORMICK and RAY BOLGER
On the distaff side, Stephanie J. Block was nominated for the trouser/title in The Mystery of Edwin Drood (2013), and, even thought she tried to turn it down, Julie Andrews was nominated for playing both Victor and Victoria in 1995's Victor/Victoria.
STEPHANIE J. BLOCK and JULIE ANDREWS
Add Robert Morse (nominee for Sugar, 1973), Tony Sheldon (nominee for Priscilla Queen of the Desert, 2011), Tom Hewitt (nominee for Rocky Horror Show, 2001), Bertie Carvel (nominee for Matilda: The Musical, 2013), and Jefferson Mays (nominee for A Gentleman's Guide to Love and Murder, 2014) to the list. Most recently, on the winners list, Hedwig and the Angry Inch yielded the coveted Tony for Best Actor Neil Patrick Harris and Best Featured Actress Lena Hall (2015).
BERTIE CARVEL and JEFFERSON MAYS
GARY BEACH, LENA HALL and NEIL PATRICK HARRIS
The late Gary Beach was two for two, nominated (and winning) in 2001 for his role as Roger DeBris in The Producers, and nominated (but losing) in 2005 for his role as Albin/Zsa Zsa in that year's revival of La Cage aux Folles. And while Mr. Beach lost the trophy to Norbert Leo Butz, both of the other Albin/Zsa Zsas won - George Hearn (1984) and Douglas Hodge (2005). Oh, and Butz dipped his toe in the drag pool in in 2007's Is He Dead?
Harvey Fierstein who has written 4 drag-related shows: Torch Song Trilogy (Best Play, 1983), Casa Valentina (Best Play nominee, 2014), La Cage aux Folles (Best Book, 1984), and Kinky Boots (Best Book nominee, 2013). He also won the Tony for Best Actor in a Play for Torch Song Trilogy, and Best Actor in a Musical for his role as Edna Turnblad in Hairspray. Tony recognition for a drag role for being in one of his shows has been granted to Reed Birney (Best Featured Actor in a Play nominee, Casa Valentina, 2014) and Billy Porter (Best Actor in a Musical winner, Kinky Boots, 2013.
If history is any indicator, Santino, Tootsie, Michael and Torch Song all have a decent shot at good news come Tuesday.