Catherine O'Hara (Waiting for Guffman, Best in Show, Six Feet Under) in Disney's Tall Tale (1995)
Doris Day in Calamity Jane (1953)
It would be remiss to feature Doris Day without mentioning her famously queer song "Secret Love" from the Calamity Jane film. The film came out during the Hollywood code when homosexuality, lesbian and the like were dirty words. Lesbians clung to Doris' performance as Calamity pining for her secret love, as cited in The Celluloid Closet.
How hot is Ellen Barkin as Calamity in 1995's Wild Bill?
Angelica Huston donned fringe chaps with a whip to play Calamity in the 1995 made-for-TV movie Buffalo Girls.
Jane Russell's portrayed a decidely more femme Calamity in 1948's The Paleface with Bob Hope.
Jane Alexander stepped into Calamity's riding boots for the 1984 made-for-TV movie Calamity Jane. She looks fantastic, but the saddle would look better on a horse!
Um, how hot was The Munsters' Yvonne de Carlo in 1949's Calamity Jane and Sam Bass? Wow!
HBO's Deadwood starred Robin Weigert as a brazen brawler of a Calamity Jane. And, she even had a little lesbian tryst during the show's two-season run.