At the end of "Temptation", Prince proclaims that he needs a woman "in the worst way." God (actually Prince with his voice completely distorted and slurred) decides to intervene at this point (totally deadpan):
God: Oh silly man, that's not how it works. You have to want her for the right reasons. Prince: I do! God: You don't. Now die.
What made it even funnier is that there is a saxophone squealing in the background during this sequence, and at points it's hard to tell if it's Prince or the saxophone.
Also in the "completely-distorted-and-slurred-voice" mode, Prince's similarly over-the-top, incredibly violent Cluster F-Bomb-throwing deadpan monologue in "Bob George".
"Rockhard in a Funky Place":
Prince: I just hate to see an erection go to waste!
This famous line from the unreleased original version of "Extra Lovable":
Prince: Baby I know my rap is hard, but not as hard as what's behind door, *dig it* door number pants
After years of distaste for YouTube and similar sites, and a poor sense of humor about himself, Prince released a single inspired by a Chappelle's Show skit at his expense, with Dave Chappelle dressed as him as the cover. Like the skit, the video also does not feature him in it, but instead has the video's (female) director/choreographer impersonating him.
"Alphabet St." accidentally provides one of the funniest moments in Prince's discography due to a sample being reused at the right moment. For context: the song begins with a drum machine beat and Prince yelling "NO!" in a high-pitched squeal. Towards the middle, there's a breakdown where Prince chants "Cat, we need you to rap!" twice before Cat Glover's guest rap comes on. The "NO!" scream is replayed at a perfect timing after the first chant, making it seem like the song has temporarily gained sentience and is protesting that it most certainly does not need Cat to rap.