- The six-minute "Sometimes It Snows in April" from Parade, stripped to nothing more than acoustic guitar, piano and vocals. It just got worse once Prince died... in April.
- Even worse. "Sometimes It Snows in April" was released on April 21, 1986. He would unfortunately die exactly 30 years later on April 21, 2016.
- "Let's Go Crazy" isn't a sad song in the slightest, but it becomes Harsher in Hindsight when Prince would be unfortunately found in an elevator on the morning of his death.
- From The Gold Experience, there's "I Hate U." It's a little over-the-top and the "courtroom scene" on the bridge is a little campy. And it's still absolutely rip-your-guts-out sad.
- The title track from "Purple Rain" is an obvious candidate.
- The seemingly cheerful pop song "I Could Never Take the Place of Your Man" is, in a bit of Lyrical Dissonance, a flat rejection of a woman that's obviously on the rebound, and it's a major downer, especially from a guy who by that point never met a bedroom romp he didn't love.
- "If I Was Your Girlfriend" from Sign "☮" the Times at least until the creepy last minute.
- While "The Morning Papers" is a beautiful love song, he was reportedly too heartbroken after his divorce from Mayte Garcia (for whom the song was written) to ever perform it live after. When Kevin Smith personally asked him why he didn't play the song live any more, Prince solumnly replied "Because Mayte isn't there to dance with me."
- In the wake of The Purple One's death, many, many, many tributes to his talent and legacy. Leave it to D'Angelo to make the mother of 'em all.
Tear Jerker / Prince
Prince has done it all - loud & proud rock & roll, R&B lust anthems, sugary pop songs, and some soul-crushing heartbreakers.