Dennis DeYoung’s cover of “Someone to Watch Over Me” on the 10 on Broadway album is a strange case.
He did switch the gender to talk about a woman, but he used the line, “I’d like to add her initial to my monogram,” which isn’t how most marriages work. You’d think he’d say, “I’d like to add my initial to her monogram.”
A John Ono Lennon homage?
Different Drum isn’t overtly male or female and Linda Rondstat did flip the girl to boy. However, in the late 60s, a woman who didn’t want to get married, and called a guy pretty would have been unusual, at least
The Mike Nesmith version sounds a little mean while the Ronstadt version sounds empowering. Nancy Sinatra did the same thing with the Beatles’ rather vile “Run for your Life”.
You probably don’t want to hear my version of Jolene, then.
Don’t know, I am always ready to be wowed.
There’s the basic framework of a pizza delivery joke here.
These Boots Were Made For Walking has been covered by dozens of male and female performers, pretty much always from a women’s perspective.
Depending on how widely you’re willing to define “pop”:
Many male singers, perhaps most famously Frank Sinatra in 1957, have performed “The Lady Is a Tramp,” which was originally written in the first person for a female character. Everyplace Frank sings “she,” the pronoun was originally “I.”
Despite the popularity of that version (and Tony Bennet’s later duet with Lady Gaga), I don’t think the song really works when done by a man. Sung by a man about a woman, it sounds critical and accusatory. As sung by a woman about herself, it’s a declaration of freedom and liberation, which is how it’s presented in its original context (the Rodgers and Hart musical Babes in Arms).
He wasn’t just the drummer, he was the bandleader: it was basically his band.
And the ‘play in recorded key’ thing was just one of his ideosyncracies.
Still, if you’ve ever been involved in the music business, you probably recall that the guy who has the well-paying gigs booked is usually the one who calls the shots… 
Reminds me of a gag I saw in a movie about the Beatles. During an audition where they had been assigned a session drummer, one of the lads (probably John) turns to him and says, “We’re doing Dizzy Miss Lizzy.” He waits a moment, then adds, “In E.”
We still do that. If we transpose a song to a different key, someone turns to our drummer and says, “Got it?” Never gets old, we’re a riot.
Also, just one more reason we’re constantly compared to the Beatles.
Drummer: hold on a few minutes. I’m going to have to rewrite my chart in the new key…
Nominee for worst counter-example: I once heard Rod Stewart’s cover of “(You Make Me Feel Like) a Natural Woman,” but he changed “Woman” to “Man.” Not only did the gender change completely undermine the lyrics’ impact, it also messed up the rhythm of that incomparable line.
That one’s right up there with Michael Bublé’s “Santa Buddy.”
Oh, I dunno, it depends. This performance doesn’t seem mean at all 
Right. I’m gonna need one of you guys to man up and fuck Santa.
I asked a friend (not Weird Al or Beyoncé), and he said that if you perform live in front of fewer than 15,000 (or whatever) people and nobody is cashing in, no one cares. He said he and his band play covers, changing the lyrics etc., in front of 200–300 people, sell around 20,000 records and they do not bother asking for permission.
Will this do?
Pretty sure Santa fucks you, not the other way around.
A competent bandleader shot-caller would want to deliver the best performance and play in the key the singer could sing in.
