Heard "Jackie Blue" on the radio the other day, and it reminded me that I was shocked when I learned that it was a guy doing the lead vocals. What other songs have you heard that were being sung by a guy you thought was a girl, or vice versa?

Jackie Blue--Ozark Mountain Daredevils. (BTW, they were OMD long before OMD was OMD)
Laughter in the Rain--Neil Sedaka. Being unfamiliar with his earlier work, I thought: "Neil..that's an odd name for a chick."
I Saw the Light--Todd Rundgren. For years, I thought this was a Carole King song.
What's Up?--4 Non-Blondes. First time, I thought it was Geddy Lee or some sound-alike.

Sunday Morning - The Velvet Underground - The first few times I heard it, I thought Nico was the singer.

When I was a small kid, I thought Edith Bunker was singing the Four Seasons' "Big Girls Don't Cry."
(Don't cry.....yiy....yiy)

"Hot Child In The City" by Nick Gilder. Totally thought it was a chick singing that song.

And the first time I heard "Jane" by Jefferson Starship I thought it was by Heart.

I didn't know Janice Joplin was a woman when I first heard her music. i thought she was a dude who sang like Axel Rose.

Also, I thought Geddy Lee was a chick when I first heard Rush.

Pete Burns of Dead Or Alive. I was never sure, then when I saw their videos I realized he was neither sex.

Steve Marriott totally sounds like a chick on the Small Faces' "Here Come The Nice."

He sings everything that high, but he's usually screaming on the other songs, which reinforces his masculinity.

+1 on Nick Gilder...Heard that song on the radio the other day, and thought, y'know, I know it's a guy singing, but it sure sounds like a girl.

When I first heard Mike Watt's Ball-Hog or Tugboat, I thought Drove Up From Pedro Sidemouse Advise and Tuff Gnarl were sung by a guy, when in fact it was Carla Bozulich.
I know quite a few people who thought The Geraldine Fibbers had a male singer, but at that point I knew better.

I have never been in doubt about any song, but Little Jimmy Scott is famous for sounding like a woman and even looking like a woman. He was born with a rare disease that makes him very androgynous, like no facial hair and a high voice.

I thought Brian Kennedy was Joni Mitchell with the song "Hollow".

"Do You Really Want to Hurt Me" by Culture Club.

I thought Heart was a Led Zeppelin soundalike.

This one fooled me too. I thought it was being sung by a man.

"Stayin' Alive" by The Bee Gees. When I heard the falsetto vocals, I thought it was their female backup singers. I kept wondering when the Bee Gees were finally gonna sing.

The Four Seasons and Frankie Valli — "Walk Like a Man (Sing Like a Woman)"

And sometimes Marlene Dietrich makes you want to turn her over just to check.

And Green Jelly's "Three Little Pigs" reminds me of my ex-mother-in-law. Does that count?

Listening to the radio, I could never figure out if these singers were male or female:

Venus by Shocking Blue

http://www.youtube.com/watch?v=U2DBcbZc3ck (lots of thick makeup there)

Na Na Hey Hey Kiss Him Goodbye by Steam

http://www.youtube.com/watch?v=jsaTElBljOE (this guy sounds like Cher)

I thought the "Calling Dr. Love" choruses in Kiss' song of the same name were sung by girls.

And I also thought "O Solo Mio" on "Elvis In Concert" was sang by Cheryl Nielsen. I was surprised to learn that she actually spelled it Sherrill, and that it wasn't a she, it was a he!

Back in the 80s, I remember some stories about people thinking that Alison Moyet's voice sounded like a man, but I never really heard it that way myself.

There is a famous Ray Charles song that Ray sang the female backing vocals because of a disagreement with the singer.

Always thought Carly Simon was a young guy with a high pitched voice when I heard her first single "That's The Way I Always Heard, etc."

I had the same reactions to "Jackie Blue" and "Laughter in the Rain."

I orginally thought 4 Non Blondes had a male vocalist also.

The first time I heard Yes (probably "Your Move/Seen All Good People") I thought the lead singer was a female.