Cross-dressing in music and opera refers to musical performers or opera singers portraying a character of the opposite gender. It is parallel to cross-dressing in film and television and draws on a long history of cross-gender acting.
In opera
An entire cross-dressing genre of operatic roles, called "breeches roles" (aka trouser or pants roles) or travesti. These are male roles performed by women, typically mezzo-sopranos but occasionally by sopranos. Some female opera singers specialize in these types of roles.
One artistic reason for breeches roles was that some storylines included young boy characters, but the actual performance required an adult's vocal strength and stage experience in addition to a high, boyish voice. Women were thus better suited to these roles than actual boys. Some examples of these roles are Cherubino in The Marriage of Figaro, Siebel in Faust, and Hansel in Hansel and Gretel. Other breeches roles were created due to the need for an adult male character to seem other-worldly (Orpheus in Orfeo ed Euridice) or unmanly (Prince Idamante in Idomeneo). In some cases, the casting of a woman may have been an excuse to have an attractive actress appear in tight-fitting trousers.[citation needed] During the Grand Opera era, women typically worn voluminous dresses onstage. Some male operatic roles originally written to be sung in the voice range of castrati (men castrated in boyhood, whose voices never descended into the normal male register) are now usually cast with female singers in male costume.
Beethoven's only opera, Fidelio, is unusual in that it features a female character who cross-dresses as part of the plot. The woman disguises herself as a young man as part of a plan to rescue her husband from prison. In The Marriage of Figaro, Cherubino dresses as a girl to avoid army duty. The part of Cherubino is thus played by a woman, who plays a man who dresses as a woman.
Peter Gabriel in the early 70s, while being lead singer in Genesis, used to wear his wife's red dress during the performance of their song '"The Musical Box" (song)', until he changed his costume for 'the old Henry' mask.
"Arnold Layne", the first released single by British psychedelic rock group Pink Floyd, is about a transvestite who steals women's clothes from washing lines. (The song was written by Syd Barrett who supposedly cross-dressed at a later point in his life when going through a mental breakdown.)
The Kinks' 1970 hit "Lola" is a song about an encounter with a transvestite.
Pete Burns, the lead singer of the new wave band Dead or Alive, cross-dressed in the band's music videos, performances, and in his appearances on TV. However, Burns is dismissive of the term "cross-dressing" to describe his style, as said in numerous television interviews and in his autobiography.
Lou Reed wrote songs about / including "T.V.'s", with the earliest example being "Sister Ray" from the Velvet Underground's 1968 album White Light/White Heat, and followed by Reed's solo album hit, the infamous "Walk on the Wild Side" from the Bowie-produced 1972 album Transformer. This song was in reference to the T.V.'s who were a part of the Andy Warhol entourage: "Sugar Plum Fairy", "Candy Darling", and "Jackie 'O'".