speakeasy said:

For me--there's only one answer to this question--> Sometimes it snows in April

There's a similar song in the Paul McCartney catalog... HERE TODAY from the Tug of War record. McCartney sings about the loss of his brother John--and all bets are off. The flood gates are opened. This is a raw, emotional, vulnerable side of McCartney--which for my money--we never saw again before or after.

Agree with you on 'Here Today' (not so much on it being the first and last time we saw that side of McCartney, but that's another discussion).

Agree with 'Sometimes It Snows," as well as those who said 'Comeback.' Even though it wasn't intended as such, in context I find 'Let's Have a Baby' unbearably sad to listen to.

bookwomen said:

If I Was Your Girlfriend is another sad song for me.

Yes, this is a great song! The desperation and sadness cannot be hidden underneath the singer's fantasy. It's like a late night phone call that spins into one sided phone sex, he knows it's inappropriate but he can't stop humiliating himself and annoying her.

Wlcm2thdwn3 said:

WHITE MANSION. Ever since the 1st time I heard it, I heard a loneliness in him

What's in your backpack today?
Will it take my blues away?
That's okay, You gotta run

Huh, check it, I don't need you to have some fun
Comin' from the land of snow
I guess I'm kinda used to cold

Read more: Prince - White Mansion Ly...etroLyrics

Wow really? This song always made me feel happy. It made me think of sunny, winter days where the sun shines off the snow for some reason...actually I never paid attention much to the lyrics.

bookwomen said:

If I Was Your Girlfriend is another sad song for me.

Yes, this is a great song! The desperation and sadness cannot be hidden underneath the singer's fantasy. It's like a late night phone call that spins into one sided phone sex, he knows t's inappropriate but he can't stop humiliating himself and annoying her.

[/quote
Love the song. Never really saw the desperation in it until your comment. I have thought about a lot of his 1980s hypersexual stuff as a kind of a compensation for his underlying loneliness. Exception perhaps is Dirty MInd where he was purposely trying to shock.

Empty Room and Sweet Baby get me a lot get me a lot lately

Krystalkisses said:

bookwomen said:

If I Was Your Girlfriend is another sad song for me.

I've always found this a sad song too. I love the performance of it in the sott movie too.

Because it is, there is sadness because he can be as close or intimate as he wishes to be, frustration, obsession and loneliness.

[Edited 7/13/16 13:21pm]

[Edited 7/13/16 13:21pm]

PurpleBabied said:

bookwomen said:

If I Was Your Girlfriend is another sad song for me.

Yes, this is a great song! The desperation and sadness cannot be hidden underneath the singer's fantasy. It's like a late night phone call that spins into one sided phone sex, he knows it's inappropriate but he can't stop humiliating himself and annoying her.

Couldn't agree more, have you listened this masterpiece at night or late afternoon, when the sun is fading away; it's just another experience.

On the Couch..not the saddest song but, he sounds so pathetic you want to just give him whatever he wants!

214 said:

PurpleBabied said:

Yes, this is a great song! The desperation and sadness cannot be hidden underneath the singer's fantasy. It's like a late night phone call that spins into one sided phone sex, he knows it's inappropriate but he can't stop humiliating himself and annoying her.

Couldn't agree more, have you listened this masterpiece at night or late afternoon, when the sun is fading away; it's just another experience.

Yes I have and I agree. Esp outside with an adult beverage as the sun is setting.

TrivialPursuit said:

"Comeback" is probably, always, going to be the saddest song he ever wrote. I mean, when your baby dies at 7-days old, and you write about that, what else can be worse? Nothing. Not divorce, not a broken relationship.

I don't really count "Another Lonely Christmas" every time, because it's ficitonal. And while many Prince songs were fictional, or ambiguous, it's his true life songs that hold more weight with me overall, whether happy or sad.

I agree about "Comeback." I would say that "Comeback" and "Until U're In My Arms Again" are the two saddest songs of his that I've heard.

There is Lonely.

Saddest song EVER!

"Cherry Cherry" is kind of sad. In a happy kind of way. A bit melodramatic, like "Another Lonely Christmas."

ldmendes said: