Already one of Turkey's most popular male singers and actors, Bülent Ersoy gained international notoriety in 1981 for a sex change operation. In a further defiance of convention, Ersoy kept the traditionally male name of "Bülent." After the operation, Bülent found herself in opposition to the extremely homophobic and transphobic regime of Kenan Evren. In a crackdown on "social deviance," Ersoy's public performances were banned along with those of other transsexual and transgendered people.
This move actually went against a centuries-old tradition of tolerance for the transgendered in Turkish society, dating back to the days when the Ottoman sultans kept young male concubines, or celtikci, who were often dressed as women. Performances by male entertainers in drag are also a time-honored and cherished tradition in Turkish culture.
From Ersoy's standpoint, the ban should not have even applied to her, as she was an actual woman and not simply a man dressed as one. To circumvent the ban, she petitioned the Turkish courts to legally recognize her as a woman. The petition was rejected in January of 1982. Days later, Ersoy attempted suicide. In 1983 she left the entertainment industry in protest of the Evren regime's repressive policies. Later that same year, Evren left office and many of his policies were rescinded.
Finally, in 1988, the Turkish Civil Code was revised so that those who completed sex reassignment surgery could apply for a pink or blue (pink for female, blue for male) identity card by which they were legally recognized in their new sex. Ersoy soon returned to singing and, over the years, she became a symbol for the increased tolerance to LGBT figures in Turkish media. The fact that she is an extraordinarily talented singer with an unequaled control of her voice, such that she is considered a diva, distracted everyone from Ersoy's transsexual status. Now semi-retired, she continues to enjoy the adoration of her many fans.
Sources: 1, 2.
Now, keeping exceptions aside, and perhaps following the "because love is blind" logic - the big question is; Does the same apply to Michael Jackson's music and fans? Or George Micheal? Or (fill in the blank)?
EDIT: What about the way around? Can't think of an artist who underwent a sex change operation (from female to male) but in the latest video of Ciara, she dresses up and acts like a boy: