Prince was a man of innumerable talents, not the least of which was mastering the art of throwing shade. One perfectly coordinated glance to the side from Prince could end careers (and arguably often did), so you can only imagine what it must have been like to feel Prince’s wrath up close. In a long, honest look back at Prince’s life, dozens of his friends and collaborators have opened up to GQ about personally knowing the Purple One, all sharing one common denominator in their relationship to the late artist: He insulted them all. Every last one. Not a publicist, ex-girlfriend, or casual acquaintance was spared a good bashing from Prince, with most recognizing what an honor it was to be on the receiving end of a Prince heckle. “This dude was ridiculously hilarious,” Van Jones notes. “He would have been one of the most famous people in the world if he had never touched an instrument, just as a comedian.” Everyone from Carmen Electra to Gwen Stefani has a story about Prince’s legendary shade. These are the best.
That time he insulted Eddie Murphy’s music:
The backstory to [the Dave Chappelle sketch] was — and this is the part Charlie doesn’t tell — Eddie had wanted to play Prince his new album. So during that basketball game, Eddie’s music was playing, via boom box, on a cassette. After that game, Prince goes over and he tosses the cassette out of the boom box, and he says, “Let me ask you a question: Do you see me stop my show to do comedy?”
That time he and Madonna traded insults:
They both started ragging on each other. Madonna said she didn’t like the script and Prince said to Madonna, “Well, I don’t like your shoes.” That’s how it all started. I was sitting there going, “Oh my God, here we go.” So Madonna told Prince, “I don’t like your shoes, either. Look at ‘em with those peace signs and zippers and shit all over ‘em.” And Prince was saying, “What are you wearing? Are those shoes or boots?” ‘Cause Madonna had on these cowboy-boot shoes. This is what happens when you get two big egos in one room. It was jokey and serious. They’re the same way.
That time he insulted George Michael’s entire life:
I have to tell him that I have to go to Paris to do this George Michael video. And he just looked at me and was like, “What do you want to do that for? George Michael? George Michael ain’t shit.”
That time he insulted Carmen Electra’s loyalty:
During that time I went out with a guy — I hadn’t slept with this person —and Prince found out. He said, “I wrote this song about you,” and then he played “I Hate U.” It was hard to hear. And it was even harder to hear the parts of the song that said it could have been a completely different way. Then to say “I hate you because I love you” — I literally cried in front of him. I think he just wanted me to hear it and know that he was really upset. Then he ﬂew me back to Los Angeles.
That time he insulted his publicist’s work ethic:
He said to me, “How many T-shirts did we sell tonight?” I said, “I don’t know.” He said, “How many programs did we sell tonight?” I said, “Prince, I don’t know — you know, I’m not sure if you know this, but I don’t do merchandising for you, I do publicity for you.” He said, “You trying to tell me that’s not your job?” And I’m like, “Holy shit, is Prince scolding me? Is Prince yelling at me?” Like, how fucking cool is this?
That time he insulted his band member for trying to out-Prince Prince:
Prince would always tell us “time is a trick.” I remember one day I was late, and he was, “You’re late, Morris!” and I said, “Well, you know, Prince, time is a trick …” It didn’t work. He was, “How about I Jedi-mind-trick that check when you don’t show up again?”
That time he insulted his publicist’s casual wear:
One time, I had taken the red-eye from L.A. to Minneapolis and went home long enough to shower, threw on a baseball cap, jeans, sweatshirt, and drove over to the studio. I went up the stairs and Prince was coming down the hall from his ofﬁce. “Going ﬁshing?” he asked.
That time he insulted Ride Along 2:
It was really not the best movie. Halfway through, we’re just, “This is so bad.” He turned and looked at me and goes, “Do you wanna leave?” I’m, “Yes, sure.”
That time he subtly insulted Gwen Stefani’s songwriting:
We went out one night in a limousine — we went to a club, I think — and it was when Jennifer Lopez had that song [sings] “waiting for tonight…” And he said to me something weird: “That’s your competition.” And I was, “What are you talking about?” Like, that was a completely different planet of music, compared to what I was doing at that time with No Doubt … He said to me [one time], “Have you ever tried to write a hit? Why wouldn’t you just try to?”
That time he insulted Dick Clark on live TV:
Totally calculated. We knew when one of those cornerstone moments was coming — it was a look he would get on his face. He called us to order in that band meeting when Dick Clark had just left the greenroom, and he had that look on his face, and he said, “I got it — here’s what we’re gonna do: When he talks to you, don’t say a word.” It was uncomfortable, watching Dick and Prince kinda go back and forth, watching him handle something that was obviously a pitch he’d never been thrown before. The answer that was given was so pared down that there’s nothing to piggyback on. Excruciatingly uncomfortable.
That time he insulted Van Jones’s ping-pong skills:
Oh my God, it was embarrassing. To the point that he wouldn’t even play me, he was just so disgusted with my inability to play. One time, he wouldn’t even move — he’d stand in one spot, and his arms were not that long and I’m six feet two. Talking crap the whole time. He’s like the worst trash-talker.
That time he pre-wrote heckles for a neighborhood bully:
When we became friends, he would tell me about the kids in the neighborhood. He’d say, “This kid Jerry, he’s going to try to do this… If he ever comes up to you and says anything, his mom’s name is this…” His mom had some funny name, and Prince literally had a spiral notebook with jokes that he was ready to tell in case the kid said anything to him. He had them written down.
That time he insulted his friend’s swag:
[One time] I was 17, I’m here dancing, and this girl was really attractive, and I’m just kind of dancing next to her. And then all of a sudden I see him walking by me with his pimp cane and his glasses on, and I’m thinking “Wow, this is cool, he’s gonna dance with us.” And then, to my left, this guy walks in front of me and gently pushed me back. Then [Prince] started dancing with her, and then he took her up to his private office upstairs. I call that game, set, match. Prince won that. How to Cockblock Somebody 101.