The writing was on the wall. After experiencing the thrill of fronting Van Halen, a band he'd idolized, Gary Cherone knew the ride was coming to an end.

Across from him sat drummer Alex Van Halen, who began the conversation by saying: “We sense that you’re unhappy and a little bit frustrated ... ”

Three years earlier, everything had started in a strangely surreal fashion. Cherone found success as the frontman of Extreme, the glam-metal outfit whose acoustic ballad “More Than Words” became an international hit. When Extreme went on hiatus in 1996, he was suddenly looking for a new musical project.

“That summer, my manager Ray Danniels – who also managed Van Halen at the time – calls me up,” Cherone later told Rolling Stone. “He goes, ‘What do you think about auditioning for Van Halen?’”

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By this point, Van Halen had already endured plenty of highs and lows. Co-founder David Lee Roth delivered his distinctive brand of showmanship, earning a reputation as one of the rock's greatest showmen, while helping Van Halen become one of the biggest bands on the planet. Following his departure, Sammy Hagar led the group through an era in 1986-96 that saw Van Halen continue their chart-topping dominance.

Now, the role was once again vacant, and Cherone’s manager saw his client as the next in line. “I said, ‘Yeah, sure. I’ll go out for the weekend, sing ‘Jump,’ come back and have a good story to tell,’” Cherone remembered, “and that was truly, truly how much I thought about it.”

Soon afterward, he was on a flight to Los Angeles. As reality started settling in, Cherone began to feel nervous. “I got off the plane in the afternoon and I remember [bassist] Mike Anthony came out," he recalled. "I’d met him over the years at some Extreme shows. I said, ‘Mike, hey, man, you’re my only ally here.’” But despite initial concerns that he'd be viewed as an outsider, Cherone was welcomed by the band.

“Alex and [guitarist] Eddie [Van Halen] came out and shook my hand. I’m holding my suitcase, my overnight bag – and Ed goes, ‘You ready to sing?’ I go, ‘Yeah. Can I go to the bathroom first?’ Then we literally went into ‘5150,’ three other songs from the Hagar catalog, and ‘Jump’ and ‘Panama’ from the Dave era.”

The chemistry in that first session was obvious, as Cherone quickly found a comfort level with the rest of Van Halen. They quickly began working on new material.

“Right from the get-go we were writing songs,” Cherone said, though he tried to quell his excitement. “Even though Eddie was real enthusiastic and he embraced me and the band embraced me, I was skeptical. I was thinking, ‘I’ll take it day to day, week to week. Let’s write another song, let’s write another song.’ I remember calling back home and everyone saying, ‘Are you in the band? You’re in the band, right?’ And I would go, ‘Yeah, I guess.’"

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Fans and Critics Were Skeptical of Gary Cherone

The new songs would make up Van Halen III, their 11th album. Van Halen launched a worldwide tour to coincide with its release – but fans and industry types seemed skeptical of Cherone.

"We’d go into a town and the radio station, there would be some mocking, you know, 'Gary Cherone, the ["More Than Words"] ballad guy, what’s he doing in Van Halen?'” Cherone told UCR in 2014. “But those same radio people saw the show and then after that, we’d see them and they were apologizing. Maybe those guys didn’t know who Extreme was.”

Van Halen III suffered a similar fate. The LP peaked at No. 4, but that was significantly lower than the group's previous albums. (The most recent four had reached No. 1.) Billboard called the album “lackluster,” while Entertainment Weekly said the lyrics fell “somewhere between less than profound and not quite abysmal.”

The ensuing tour, while promising, was also met with lukewarm ticket sales even though the band delved deep into its catalog of songs. "It’s funny, it was kinda pre-YouTube, but there were rumors going around, 'Oh, they’re playing ‘Mean Street’ for the first time in 20 years,' so that worked in my favor," Cherone told UCR.

Cherone said he was taking it all in stride. “I remember being stressed out, but I felt comfortable," he told Rolling Stone. "For me, all during the making of the record, I couldn’t wait to go on tour because that was my comfort zone. I was dying to get out there and play some new songs, play some old songs. Of course, you’re going to get the die-hard fans who are never going to like you no matter what you do. But most of the time, 90 percent of the audience was thrilled that I was singing the old shit. Two-thirds of the set, if not more, were songs Van Halen fans hadn’t heard in a very long time.”

The tour cycle came to a close at the end of 1998. Even with lower-than-expected profits, Van Halen seemed energized by the trek. “I think, maybe, me having some young legs – I was a little younger than those guys. I’m not saying I pushed them, but I think they embraced it,” Cherone told UCR. “Because it’s my nature to run around and have fun like a carnival monkey, so Eddie was running around [during performances too]. Everybody seemed to be happy.”

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Alex Van Halen Breaks the News to Gary Cherone

Van Halen assembled to work on new music at the start of 1999, but Cherone said he sensed that the band had “started to get a little dysfunctional. ... I think Eddie started drinking a bit. It wasn’t bad, but it wasn’t going in the right direction. Also, I wasn’t in a great place mentally. I had some things going on in my personal life that affected me.”

That's how Cherone ended up having that heart-to-heart with Alex Van Halen. Acting as the band’s figurehead, he was tasked with excusing Cherone from his duties on Nov. 5, 1999. “I knew the end was near,” Cherone admitted, adding that he only wished they could have completed that second album together.

Unlike the drama-filled departures of Roth and Hagar, Cherone left amicably. He’d later describe the parting as “mutual,” and maintained a friendship with Michael Anthony.

Extreme reformed in 2004 and began touring and occasionally releasing new material while Van Halen took a break for several years before reuniting with both Roth and Hagar at various points.

Cherone continued to reflect happily on his tenure with Van Halen, even if it was short-lived. “At the end of the day, I’m gonna say, ‘Hey, I was one of the three singers in the mighty Van Halen,’" he told Rolling Stone. "You can’t take that away from me.”

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Gallery Credit: Nick DeRiso

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