- 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.
- 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.