Looking for songs that are narrated by a particular character. The narrator is explicitly a particular gender, but the performer is the opposite gender.
Excluding performances in drag, please. So, for example, Dame Edna singing a song with a female narrator wouldn’t count.
House of the Rising Sun is a song narrated from the point of view of an explicitly female prostitute. (It’s been the ruin of many a poor girl, and God I know I’m one).
It has been performed by male singers, including Bob Dylan.
Fernando, by Abba, narrated by an old man reminiscing with a friend about a battle they fought in their youth. Well, it doesn’t explicitly state the narrator’s gender, but I think a male is more likely. It is, however, sung by the girls. The verses at least
Leva’s Polka is, according to Wiki “sung from the point of view of a young man, about a woman called Ieva (dialectal for the name Eva or Eeva in standard Finnish) who sneaks out and dances the polka with him all night.” However, in a particularly noteworthy performance, the lead singer is female.
Fast Car by Tracy Chapman is about a female character (“I work in the market as a checkout girl”), but was covered by Luke Combs without any changes to the lyrics.
The Beatles covered the Shirelles’ “Boys.” They changed the “I” to “my girl” in the verses, but kept the titular “boys” in the chorus. Not really a change in perspective, though — it sorta implies they’re singing about “boys [like me],” while the Shirelles sang about “boys [like him].”
Another John Prine composition: Bette Midler’s cover of “Hello in There” keeps the original perspective from an elderly man, I’m pretty sure. Most of the lyrics could be from either the husband or the wife, but I think he addresses the wife by name. I’ll check now.
I don’t know if this counts, but Sixpence None The Richer did a cover of There She Goes, a song originally sung by a male about a female. But there is nothing in the song that explicitly indicates that the singer is male. The Sixpence None The Richer version could easily be a female singing about a female, and in more recent years has often been interpreted as such.
Stormy Weather (1933). This is a torch song written by Harold Arlen and Ted Koehler and originally sung by Ethel Waters, but since then has been sung by many a male singer (e.g. Duke Ellington, Frank Sinatra, Bob Dylan, etc.). It is easy to change because you can switch one word and then it becomes about woman instead of a man. I know I sang it after first hearing it sung by women (or vice versa) as part of a choir ensemble which is why it immediately came to mind when I saw this topic.
You can decide whether or not it counts, since the pronouns are changed, but “The Lady Is a Tramp,” famously recorded by Frank Sinatra, was written (in the context of the Rodgers and Hart musical Babes in Arms) for a female character. Everywhere Frank sings “she,” it was originally “I.” The “Lady” of the title is meant to be the narrator herself.
The frontmen of the bands Saves The Day and Say Anything, Chris Conley and Max Bemis, have a side project called Two Tongues that consist entirely of duets. Well, some of them are more like dual vocals instead of the traditional duets where the singers are responding to each other, but a lot of them are duets. Some of those, in turn, don’t actually specify the gender, but in some of them Chris, with the higher voice, is singing as the woman. So they made several original songs with the gender switched from the beginning.