In 1998, Dana International won with "Diva".
She is also sings, "Free", (1999 Finalist),
But, my favorite: Love Boy דנה אינטרנשיונל - לאב בוי
Dana International:
Cohen was born in Tel Aviv, Israel, to a family of Yemenite-Jewish descent.[2][3][4] Her paternal grandparents lived in Petah Tikva. She is the youngest of three children, and was named after an uncle who had been killed during a terrorist attack.
Though assigned male at birth, she identified as female from a very young age. She wanted to become a singer from the age of eight, when she watched Israeli singer Ofra Haza perform her song "Chai" in the 1983 Eurovision Song Contest.[citation needed] Although the family was quite poor, her mother worked to pay for her music lessons, and she stated that her childhood was happy. She came out as transgender at the age of 13.
Dana International took her stage name from a feminized version of a childhood friend Daniel, who died in a car accident.[citation needed]
https://en.wikipedia.org/wiki/Dana_International