This article examines the significance of cross-dressed burlesque comedy and satire of two iconic Australian performers: Barry Humphries, who played a 'farewell tour' in 2012-13,and Reg Livermore, who retired in 2011 and is best known for his 'perfect' portrayal of Frank n' Furter in 'The Rocky Horror Show' (1974). Both of these performers are among the most influential male-to-female burlesque entertainers of our time. Humphries, born in 1934, and Livermore, born in 1938, are consummate burlesque performers, who worked together at Phillip Street Theatre in the 1950s and set their sights on the West End early in their careers. Both performers presented solo shows in London in the 1970s, that marked career turning points. Through their burlesque performances, Humphries and Livermore have outraged and charmed audiences in Australia since the 1970s. Livermore's one-man shows are associated with 'truculent avant gardism' by international critics, and Humphries with alternatively savage and gentle, but always topical, satire. Humphries and Livermore provided an extended satirical attack on a range of targets and defined an era of peculiarly Australian burlesque. Both parodied gender constructs and categories. Humphries charmed audiences with his ability to draw out burlesque performances from guest performers on his television chat shows, and his use of burlesque-inspired satire has increased gradually over his fifty-six-year stage and television career. Livermore performed some of the most provocative burlesque acts in Australian theatre history in his one-man shows, reprising some of his characters after a long interval in the 1990s.