To most of the outside world, Prince was shy, standoffish, and barely spoke above a whisper, if he spoke at all. Among friends, he was a comedian with a bottomless bag of gags, pranks and practical jokes. In observance of the late musician’s birthday — he would have been 60 today — we pay tribute to his comic side with seldom-told tales from bandmates, friends and others close to him collected over the past two years. We hope to make this an annual article, so hopefully there are many more like this to come (hit me if you’ve got a good one). Thanks to everyone who shared their memories — there’s no better way to start than with this one:
MARC ANTHONY (Singer/friend)
He was absolutely hysterical. His image was so serious, but he loved to laugh. That’s the first thing that took me aback — how funny and how quick he was. He didn’t trust too many people, but once he felt safe with you, it was some funny shit, man. I remember loving his laugh and loving seeing his face like that, because it was so rare.
I’m listening myself as I’m talking to you, like, wow, I’m just so blessed. [Wistfully] He was a beautiful man, a beautiful man.
DEZ DICKERSON (Guitarist, 1979-83)
You know the  mugshot? This is where it came from. We were flying from Jackson, Mississippi and we were spread out all over the plane, but Prince and [keyboardist Matt Fink] were seated together. Prince opened the overhead bin where they kept the emergency gear and one of the things in it was a bullhorn. And I guess he decided he’d like to have a bullhorn, so he snatched it out of the bin and initially gave it to Matt to put in his bag but it wouldn’t fit. So Matt came up to me, 15 rows back, and I’m like “This is gonna end badly but okay, he’s the boss.” I found a way to put it in my bag, but there was a lady who was so incensed that these bizarre-looking people would dare to do this, so she told a flight attendant who told the pilot, and they called the sky marshals. “Ladies and gentlemen, someone has stolen a piece of airline equipment and the sky marshals will be conducting a row-by-row search.” When they got to my row I said, “Yeah, I’ve got it, but I didn’t take it — they did.” Prince stood up, huge smile, thought it was hilarious and was just like, “Take me” — and they did, took him and Matt off the plane and to jail and the whole nine. But because people at the police station knew who he was, they just ended up joking around and signing autographs until management got him out.
RAPHAEL SAADIQ (Artist-Producer/friend)
I did a festival on a bill with him and Chaka Khan in Copenhagen [in 2011]. I was onstage, the crowd was having a good time, partying, and I did a spin and the crowd went nuts. I’m thinkin’ “I’m really killin’ it right now!” — and then I turned around and Prince is onstage, dancing behind me. I was killing it — but I wasn’t killing it that much!
He hated it when I cursed. I thought it was a joke, I mean, I’m from New York, I curse quite a bit. I was like “Come on, bro, you f—ing kidding me?” It made him so uneasy because I kept f—ing with him, “You’re shitting me, right?” Finally he was like, “Marc, if you curse again my makeup will come off!” [Laughs] And I totally stopped cursing in front of him — every time I’d see him I was on my best behavior. I felt like he was the principal.
He’d have these hilarious characters — there was this old dude who talked kinda like this, that was one of the most common. A lot of those voices ended up being transferred into The Time shtick, some of those voices that [frontmen Morris Day and Jerome Benton] did.
TED COHEN (Warner Bros. artist development, on tour with Prince 1980-85)
On the  “Dirty Mind” tour he had Morris come out for a few dates to watch and start rehearsing becoming Morris Day — Morris is his real name, but the character was created as an alter-ego of Prince, the hipster pimp version. Prince started talking to me as Morris: [Morris Day drawl] “Heeeey,” and then slip right into [deep Prince voice] “When are we going back to the hotel?”
This would be horribly politically incorrect now, but when we were in airports and he saw an empty wheelchair he would sit down in it, put on a pair of sunglasses and have us push him out onto the concourse. We’d disappear into the background and he’d slowly slide down onto the floor and see how people would react — it was all in fun, it wasn’t meant to demean anyone, but it was an interesting [study in psychology]. Some people would act like they didn’t see and walk on by, but there’d always be someone who’d be horrified and say “Oh this poor man!” Once someone once made the first move, people would come over and be like “Is he okay?”
BOBBY Z (Drummer 1979-86)
Sight gags, slapstick, if you tripped it was funny. He would approach you from the left and tap your right shoulder, that was one of his favorites.
The funniest ones were the tricks he played on people from other bands we were touring with, like The Time and Vanity 6. Once we put maple syrup on Morris’ hotel-room door. He was always impeccably dressed, so the last thing he wanted or needed was somebody sneaking up on him and squirting mustard on his white brocade jacket.
Prince threw the greatest food fight in rock history. We were touring with The Time and we were backstage at the Stanley Theatre in Pittsburgh and Jerome hit me with an orange. It left a mark on my suit and we got to the dressing room and Prince said “What happened to you?” “Jerome threw an orange at me” — and that was it, he was off and running. Strategies were drawn and people went to their camps and plotted and security helped out. This turned into a two- or three-day event, with [tourmates] Zapp in the middle.
He had our security guys kidnap members of The Time while they were onstage performing. It was hilarious seeing the audience’s reaction when one guy at a time was snatched and taken as a “prisoner of war” and somebody from our band would take their place. On the last show of the tour they kidnapped [Time guitarist] Jesse Johnson and Prince took his place, wearing a hat like Jesse’s. Prince and Matt and somebody else finished the set, and they didn’t miss a beat!
[Time members Jimmy Jam and Terry Lewis] were wearing these perfectly tailored Hefty-bag suits with shower caps for hats. They were armed with eggs. Matt and I were running from them and we burst into [Zapp leader] Roger Troutman’s dressing room and he’s got a party going on and suddenly we’re in his world. I didn’t want eggs thrown into this poor guy’s dressing room, and of course we got pelted the second we left. Somehow, after the show, after a half hour of battle, these trays of pies suddenly arrived. I don’t know if Prince ordered them during the fight but everyone was throwing them and then Jesse broke free — he’s in handcuffs, running around in the middle, mad. It was like a choreographed 1930s movie. Prince had been off in his general’s quarters, plotting, but they eventually got him with pies. He took it so seriously: He approached a food fight like he played music, it was the real deal.
Jesse was not happy about being held hostage. The kidnapping kinda went a little too far.
It was incredibly fun but there was an element of fear. It made [the band rivalries] in “Purple Rain” look tame. The espionage was so intense, it was physical and had weapons: maple syrup, toothpaste, eggs, yellow mustard. Promoters were starting to get nervous. It just didn’t look right.
One night in ’81 he did a show at Flipper’s in L.A. that we videotaped. The next night I’m home and Prince calls me up: “Hi Ted, it’s Prince. I got your number from [then-comanager] Steve Fargnoli. Can I come over?” “Uh, sure!” He comes over, “You’ve told me about music videos, can you show me ones you like?” MTV hadn’t launched yet; I had been trading videos with everybody at the labels and Prince hadn’t done a music video yet, so for the next two hours he just sat there, like David Bowie in “The Man Who Fell to Earth,” watching the screen — no smalltalk, barely a word. I must have showed him 30 or 40 videos. He says thank you and leaves. The next night the phone rings again, “Hi it’s Prince, can I come back?” Sure. Again, no smalltalk whatsoever: “What else have you got? What have you got that’s shot in black in white?” He stayed for another two hours and left.
CASSANDRA O’NEAL (Keyboardist, 2009-2016)
We were doing a residency at Madison Square Garden in 2011 and we had an aftershow and the late, great Sharon Jones, who opened some of the shows, was playing. We’re watching them and they’re killing it, she’s so dope, Prince is sitting next to me, it’s a party, it’s the cap on a perfect day. Prince had on these leggings and he says (low voice) “You like my pants?” “Yes, they’re gorgeous.” We go back to listening — you didn’t really strike up conversations with him, you just let him lead. Then he says “They’re killing, aren’t they? ” “Oh yes.” “I should give her some money. Do you have any money?” because he didn’t carry cash. I had a $50 bill so I gave it to him and he says “I’ll be right back, save my seat.” So he melts into the crowd, comes back and says “I gave your $50 to Questlove.” “You did? Oh, okay.” So later I run into Quest and we made some smalltalk and I said, “By the way, did Prince give you a $50 bill?” He says [surprised], “Yeah, he did.” And I kinda jokingly said, “He was supposed to do something else with it, can I have it back?” And he said “No, because every time he sees me he always gives me a piece of money and I hang it up on my wall. So this 50 will make $163.25” or some very specific number like that — he really knew how much Prince had given him. He was very nice about it, then he says, “I can’t give you back that 50, but here, you can have this instead,” and gave me a $100 bill!
REBEKAH ALPERIN (Universal Music Publishing/independent consultant, 2002-2004)
One time he was playing a stadium in Hong Kong for maybe 15-20,000 people. He ran backstage while the band kept playing, said “Hello Rebekah,” in that deep voice, walked over to this full-length mirror, looked himself up and down and did that funky thing with his head just like in that [2005 Fred Armisen “Saturday Night Live”] “Prince Show” skit and puckered up his lips — like, “I’m Prince!” — and ran back onstage. I fell over laughing when I saw that skit, they had it so perfect.
(Head here for even more great stories in part 2: Phone gags, a stuffed penguin and “sharing a bathroom with Justin Timberlake.”)