The guitar toss was a staple of Prince's showmanship — from the casual "drop off the back" technique to launching the instrument feet into the air. In one famous case, following an all-star jam with Tom Petty, Steve Winwood and Jeff Lynne, he seemingly threw his axe into the void, spawning a spinoff legend. (His guitar tech reportedly caught it and handed it, per Prince's instructions, to Oprah Winfrey.)

These tosses brought only mystique, not harm — after all, Prince was damaging his own equipment. But in one famous case, the Purple One sacrificed a guitar from someone else's collection: the prized 1961 Epiphone Crestwood belonging to the Roots' "Captain" Kirk Douglas. Was is it an iconic funk-rock spectacle or just really rude?

The infamous act occurred during a March 1, 2013 taping of Late Night With Jimmy Fallon, where the Roots serve as house band. Prince — who, in another idiosyncratic moment, challenged the host during the booking process to an off-air ping-pong match — was on-hand for a live performance of his thunderous single "Screwdriver." After storming through the track with his backing band 3rdEyeGirl, the frontman switched to the Crestwood and unearthed 1979 deep cut "Bambi." He finished with a volatile wah-wah flourish, hurled the six-string above his head and strutted backstage after it crashed to the floor, bathing NBC's Studio B in a wave of feedback. (Fallon walked onstage for the show-ending promo, awkwardly laughing as he observed the wreckage.)

The headstock was broken, as was Douglas' spirit. "I went through some complicated emotions in that very moment," he told Consequence of Sound. "Initially it was kind of negative. After it happened, I had my guitar in pieces. I went to Prince, and I was like, 'Hey, you broke the guitar. If you don't mind, could you sign it at least?' And he was like, 'Oh, I haven't signed anything since the '70s.'"

So how did all this happen? Why was Prince, a performer with very specific taste, even playing someone else's gear? Turns out his guitar tech forgot to bring his intended instrument to Late Night, and Douglas — a big Prince fan — was happy to share his own. "The crazy thing," he later tweeted, "is the only reason that guitar was in [30 Rockefeller Center] was because I was rehearsing for a Prince tribute at Carnegie Hall [that] week."

Douglas' act of friendship only bred destruction. "Purple Pain," he tweeted after the taping, along with his damaged instrument. "Maybe it's because I'm a dad," he added, "but I think framing the guitar is a little like rewarding bad behavior." And though Prince never exactly explained why he went for such a risky toss, he did rectify the situation: apologizing and making arrangements to have the Epiphone fixed. It also allowed Douglas to make some gratifying connections with other music giants.

"Well, a lot of good came from that," he told Consequence of Sound. "A lot of artists who I admire reached out to me saying, 'Oh, that was a really shitty thing he did' or saying, 'That guitar, I know exactly where you can get another.' Jackson Browne reached out with a listing of where to find another Epiphone Crestwood. That, to me, was super amazing. Jackson Browne reached out to Elvis Costello, and Elvis Costello passed that information on to me."

He added that he didn't take the toss personally because this exact scenario has unfolded with others. "The reality is this sort of thing has happened with many people," he said. "Other guitar players came up to me and were like, 'He did the same thing to at a jam session.'" The Roots member also theorized that Prince's massive fame has altered his perception of personal interactions and "human constructs" — maybe he didn't even think breaking the guitar was that big of a deal. Plus, Douglas wound up with an all-time classic rock story.

"I told Chris Rock about it, and he was like, 'Oh, congratulations! You too now have your own Prince Was an Asshole to Me story," he added. "I feel like I'm part of this club of people who've been wronged by him. For all I know, he could have just even known, in all of his genius, like, 'Watch, I'm gonna hook this kid up. I'm gonna break his guitar so he can have this story and talk about it for the rest of his life.' If that was his thought, he would not be wrong about that."

He even used the Prince encounter to fuel his own songwriting: That memory spawned the song "Little Friend," a highlight from Douglas' debut solo LP, 2019's Turbulent Times, issued under the name Hundred Watt Heart.

"'Little Friend’ was actually composed on the guitar I purchased with the money left over from the repair of the guitar he actually broke," he told Rolling Stone. "I recorded the song with the Crestwood. The lyric comes from the emotion of the moment of that time where I was upset, but in retrospect it’s one of the coolest things that has ever happened to me. He’s probably looking down, saying, 'I made your old ass guitar way more interesting, paid you for your troubles and gave you something cool to write about … you're welcome."


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