Songs about a person who is the same sex as the singer

Pearl Jam - Sleight of Hand
“Routine was the theme
He’d wake up, wash and pour himself into uniform
Something he hadn’t imagined being”

And, of course, Jeremy.

JRB

  • Jim
  • The Truth (about M****** D*****)

Alanis Morrissette - Mary Jane
Tom T. Hall - The Year that Clayton Delaney Died
Concrete Blonde - Tomorrow Wendy

The bitch in question is a man.

Come Together - The Beatles

Lido Shuffle - Boz Skaggs

The Cisco Kid - War

Hymn for a Sunday Evening” from Bye Bye Birdie

A lot of religious songs are about God/Jesus. A lot of men sing songs about God/Jesus (assuming God is male)

Gerry Rafferty wrote a song about his mother. The song is Mary Skeffington.
Olivia Newton-John did a remake of the song, so she sang a song about Gerry Rafferty’s mother.

Jackie Brown - John Mellencamp

Great list! The Kinks Apeman doesn’t really fit though, does it? I remember it being about the singer wanting to be an apeman. The Kinks Lola fits — ambiguously.

JEB LOY NICHOLS - Say Goodbye to Christopher

Yesterday I saw Christopher
In a parked car on Ludlow Street
Turning around looking over his shoulder
Talking to someone in the back seat

I was walking on the lower east side and suddenly there was a street sign that said “Ludlow Street”. I just stood there, in the rain, and let this song unreel through my head.

Jeb usually does more rootsy (Folk/Reggae/Bluegrass/Brass) tunes… here’s one of my favorites.

Not For Keith by Peter Hammill

“In Germany, his days finally caught him;
I won’t insult his memory with long-distance grief.
Tears and wakes weren’t his style:
not him,
not for Keith.”

In 1984, Rick Springfield reached #27 on the U.S. Billboard Hot 100 with a song complaining about people who confused him with Bruce Springsteen:

Another song by a guy about someone called Keith, though I think that’s another Keith than in the Hammill song, because Keef’s days never finally caught him, as we all know this guy’s immortal.

This is a thing, possibly even good for a thread unto itself: Songs that had to get the lyrics re-gendered depending on the gender of the singer.

Another similar case was “This Old House” (or “This Ole House”) by Stuart Hamblen, but recorded by many others too, including famed female singer Rosemary Clooney.

Ostensibly a song about an old decrepit falling-apart house, it is actually about an old widower who is preparing to die, sung in the first person. (The singer compares himself to the old house.) Despite being in the first person, there are some gender-specific references (“This old house once knew my children, this old house once knew my wife.”)

In the Rosemary Clooney version, she fixes that by putting the song in the third person instead (“This old house once knew his children, this old house once knew his wife.”)

ETA: It doesn’t work perfectly. In the original, Hamblen sings “Ain’t gonna need this house no longer, I’m a-getting ready to meet the Saints”.

In Clooney’s version, she sings “Ain’t gonna need this house no longer, he’s a-getting ready to meet the Saints” – It’s not clear who “he” refers to. There are many references of “he” in the song, and it’s hard to tell which refer to the old guy, and which refer to the personified house. I never understood that until I learned of the original Hamblen words, which are not ambiguous like that.

Adia - Sarah McLachlan
Sunny Came Home - Shawn Colvin
Maria - Blondie
Rip Her to Shreds - Blondie

Bat for Lashes - Laura. About a friend who still wants to party, but everyone else has stopped. Beautiful melancholy song.

Johnny Cash - a Boy Named Sue

Kate Bush - Babooshka

I am going to quibble.

The song is as much about Jan as it is about Tweeter, The Monkey Man or the Undercover Cop. And it seems that Tweeter is trans.

“Lucky Man” by Emerson Lake and Palmer

Also “Goo” from the same album.

“Sweet Jane” - Cowboy Junkies version.

“Children’s Story” Slick Rick

“AJ Scratch” Kurtis Blow

“A Shogun Named Marcus” Clutch