Imagine the scene: You’re a hot-shot young guitarist who has just been given the dream job, playing in Ozzy Osbourne’s band. Your first show? Inside a prison in front of a crowd of inmates.

That’s how things played out for Zakk Wylde, who made his live debut alongside Osbourne on July 28, 1987, during a gig at the U.K.’s Wormwood Scrubs Prison.

Wylde had been plucked from obscurity thanks to a mix of talent and timing. Jake E. Lee's five-year tenure ended in 1987, leaving Osbourne once again searching for a guitarist.

“You can imagine how many guitarists sent in their resumes. It was fucking mind-boggling,” Osbourne later told Guitar World. “So after a while, Sharon started bugging me, ‘When are you gonna listen to these tapes?’ I just didn’t want to deal with it. I’d tell her, ‘Whatever, whatever.’

“So one morning I decided, ‘I gotta do this,’” he added. “I stuck my hand in a bag and pulled out a tape, and Zakk’s tape was the first and only one I listened to.” His playing immediately blew Osbourne away, and, after a couple of face-to-face meetings to make sure things clicked, Wylde was officially handed his dream job.

“It was incredible,” Wylde said of the life-changing gig. “All my friends said, ‘Hey, Zakk, can we get free tickets, and can we meet Ozzy?’ Suddenly, I had more friends than I ever imagined.”

Scrubs, a metal band made up of inmates at the prison, had begun garnering attention in the U.K. around the same time via a pair of singles. The group invited Osbourne to perform at Wormwood, and he was surprisingly open to the offer.

“We wanted Zakk to fit in with the rest of the band before we went into the studio, but I didn't want the press looking down his ass at every show,” Osbourne told Hit Parader (as relayed by Metal Injection), adding that performing in a prison “would give us the chance to get the feeling for the road without worrying about press reaction.”

Osbourne and his band accepted the Wormwood gig, and at one point even considered a full tour of various penitentiaries. The Wormwood show, played in front of criminals and armored guards, went about as well as you’d expect.

“The whole thing was bizarro land,” Wylde later told Metal Hammer. “We performed in front of these fuckin’ lifers. All I could think was, ‘I hope I pass this fuckin’ audition.’”

Wylde was just a young man at the time of the prison gig and reportedly got some extra attention from the inmates. “I was clean-shaven, 20 years old, weighed about a buck-fifty,” he told Guitar World. “I was the closest thing those guys were gonna see to Farrah Fawcett. So I was just thinking I best not fuck up – because Ozzy might have left me in that jail.”

Instead, one of the longest musical partnerships of Osbourne’s legendary career grew from this strange beginning. Since that prison performance, Wylde and Ozzy have remained close friends and collaborators, developing a musical partnership that has spanned decades.

“My relationship with Ozzy is about so much more than the music,” Wylde told Metal Hammer. “I’m literally always a phone call away. If [the Osbournes] need me to go over and feed the dogs while they’re on vacation? No problem. Need eggs and milk? I got it.”

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