English soul singer Dusty Springfield (born Mary Isobel Catherine Bernadette O’Brien) was one of the top female artists of her generation. She took her stage name from her first group, the folksy-sounding Springfields, but left soon after to pursue a solo career that would last nearly four decades; although her popularity dwindled beginning in the 1970s, the inclusion of “Son of a Preacher Man” on the Pulp Fiction soundtrack triggered a revival. Her album Dusty in Memphis was ranked as the 89th greatest of all time by Rolling Stone, and she has been honored in both the American Rock and Roll Hall of Fame and the UK Music Hall of Fame. Springfield’s lesbianism was the focus of an off-Broadway musical based on her life.
Vasil Trayanov Boyanov, who goes by the stage name Azis, is a gay Bulgarian Roma pop-folk singer who performs in a drag-ish hodgepodge of outfits. Azis boasts an impressive discography including dozens of singles, and his concerts sell out quickly. His atypically-gendered modeling and open homosexuality have been sources of controversy, as when billboards featuring him kissing his then-husband while shirtless were censored for being too graphic. Outside of music and scandal Azis was narrowly defeated in a run for parliament as a member of the Eurorama party. For his accomplishments Azis was declared the 21st most important Bulgarian of all time in 2006 by the television program Velikite Balgari.
Screenwriter, lyricist, and activist Gazal Dhaliwal is an outspoken member of India’s increasingly public transgender community. She created a documentary while in film school, To be…Me, which features interviews with fellow trans people and summarizes current medical and legal perspectives. She has appeared in blogs, on the TV series My Big Decision, and with her parents on a high-profile talk show‘s episode on “alternative sexualities” (available for viewing here). In her appearances she stresses her post-transition happiness and the variety of gender roles that trans people are drawn to.
Anthony Perkins’ role of “Norman Bates” in Psycho (and its sequels) was among the most iconic to come out of thriller director Alfred Hitchcock’s canon and an overwhelming presence in the actor’s life. Perkins had already been a theater actor and won awards for both stage and screen, like the part of a young Quaker man in Friendly Persuasion, a movie President Reagan later offered to Mikhail Gorbachev as a model of conflict resolution. Perkins also had a respectable singing voice, acting in several musicals and releasing three pop albums, though he never managed a career from it.
Perkins’ sexual orientation is subject to some interpretation. Although he allegedly had affairs with a number of male celebrities, he did marry and had at least one encounter with a different woman earlier in his life. He is popularly referred to as both homosexual and bisexual though he never openly called himself either; in fact, he suggested in one interview that psychotherapy had enabled him to have relationships with women.
The tux-wearing, blues-singing, self-described bulldagger known as Gladys Bentley played a somber tune in her recordings but switched out the lyrics to popular melodies at her New York City live performances to make the audience blush (and enrich her flirting with the available ladies). When the Depression hit and prohibition ended, taking with them the popularity of her music and the tolerance for outspoken lesbianism, she found a brief resurgence in the gay bars of San Francisco, but retired to become a minister.
Bentley’s dramatic retirement, marked by an article in Ebony magazine entitled “I Am Woman Again”, was a public departure from both show business and homosexuality. In the context of high-profile McCarthyism witch hunts her decision made sense; looking back it makes for a striking example of how an individual’s insistence on a certain identity is not above questioning. (One possible explanation for her subsequent marriage is that she was attracted to men as well as women, but given her claims to have married a woman in a civil ceremony and her bookings in lesbian bars, heterosexuality seems unlikely, and in a subsequent interview she implied that she was having a relationship with both a man and a woman.)
Stephen Sondheim penned the lyrics and music for some of the 20th century’s most iconic musical theater productions over a career spanning more than five decades, from Company to Sweeney Todd. His mentor, Oscar Hammerstein II, was a theatrical master himself, and his early tutelage involved writing entire musicals for critique. West Side Story, Sondheim’s Broadway debut, earned numerous awards and spawned a film adaptation. In later years Sondheim took on darker projects that have been criticized as “inappropriate” for musical theater but won him accolades and an enduring impact on the genre (and enough uses in film and television to fill an IMDB page).
American jazz and swing musician William Lee “Billy” Tipton toured for decades with various bands (including his own, the Billy Tipton Trio) before settling down in Spokane, Washington, to work for a talent agency and play a steady stream of local gigs. Although he was never a big name in music circles, he recorded two respectable albums and made a successful career out of playing the piano and saxophone, all while prioritizing a healthy family life. Greater recognition came after his death when a paramedic team revealed that he had been assigned female at birth and the news hit the headlines, prompting country-wide amateur speculation on the alleged tragedy of a woman forced to live as a man in order to survive in the music industry (or how Tipton might have been crossdressing for the thrill of it). Given Tipton’s lifelong insistence at presenting as male, the interpretation that he was a happy and successful trans man appears more likely.