Jim Bailey, who helped introduce American television audiences to drag with his frequent appearances on classic series such Here’s Lucy, The Carol Burnett Show and The Tonight Show Starring Johnny Carson, has died at age 77. A message posted to the entertainer’s official website on May 30 reads: “Heaven is getting a fabulous show tonight with standing room only! Rest in Peace Our Sweet Prince.”

Bailey’s manager Stephen Campbell told The Hollywood Reporter that his client died of cardiac arrest from pneumonia complications.

While there were many male comics such as Milton Berle who dressed in drag for easy laughs, wearing a gown was serious business for Bailey, who had studied opera at the Philadelphia Conservatory of Music. He first gained renown for his transformation into pioneering female comic Phyllis Diller, and eventually added other popular entertainers including Barbra Streisand, Peggy Lee and Judy Garland into his act. Bailey even performed as Garland opposite Liza Minnelli at The Flamingo in Las Vegas in 1973, recreating a famous mid-’60s concert by Garland’s daughter and her late mother in London. Bailey and Minnelli became close friends.

Bailey, who considered himself a “character actor,” performed around the globe at many prestigious venues during his career, including New York’s Carnegie Hall, London’s Palladium, and even at the 1978 Super Bowl. Besides numerous appearances on variety series and talk shows, Bailey also appeared as one of TV’s first transgender characters in 1988 during a guest spot on the sitcom Night Court.