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 Alex Van Halen, the group’s drummer, 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 had 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, the singer found himself looking for a new musical project. “That summer, my manager Ray Danniels – who also managed Van Halen at the time – calls me up,” Cherone recalled in a 2012 interview with Rolling Stone. “He goes, ‘What do you think about auditioning for Van Halen?’”

By this point, Van Halen had already endured the highs and lows of two previous singers. Original frontman David Lee Roth delivered his distinctive brand of showmanship, earning a reputation as one of the rock's greatest singers, while helping Van Halen become one of the biggest bands on the planet. Following his departure, Sammy Hagar led the group for a successful tenure from 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 explained of his expectations. “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 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.’” Despite initial concerns that he'd be viewed as an outsider, Cherone was welcomed by the band. “Alex and Eddie 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. The group quickly began working on new material. “Right from the get-go we were writing songs,” Cherone noted, adding that he did his best to quell his own 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.’"

The new songs would make up Van Halen III, the group’s 11th album. The band launched a worldwide tour to coincide with its release. Despite excitement for the new material, fans and industry types seemed skeptical of the new singer.

"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?'” the singer noted during a 2014 interview with UCR. “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 was met with a collective yawn. It peaked at No. 4, with sales significantly lower than the group's previous albums (the most recent four had all reached No. 1). "Without You" was the LP's only significant radio hit. Billboard called the album “lackluster,” while Entertainment Weekly said the lyrics fell “somewhere between less than profound and not quite abysmal.”

Watch Van Halen's 'Without You' Video

The ensuing tour, while promising, was also met with lukewarm ticket sales despite the fact that 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 recalled.

As for the stress that came with fronting one of the biggest bands on Earth, the singer took it in stride. “I remember being stressed out, but I felt comfortable," Cherone admitted. "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, the band 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 opined. “Because it’s my nature to run around and have fun like a carnival monkey, so Eddie was running around [during performances]. Everybody seemed to be happy.”

At the start of 1999, the members of Van Halen assembled to work on new music. Even as they penned new tunes and recorded demos, Cherone sensed 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," the singer confessed. "Also, I wasn’t in a great place mentally. I had some things going on in my personal life that affected me.”

And so Cherone found himself having a heart-to-heart with Alex, the drummer acting as the band’s figurehead, tasked with excusing the singer 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-laced departures of Roth and Hagar, Cherone left amicably. He’d later describe the parting as “mutual,” and maintains a friendship with bassist Anthony to this day.

Extreme reformed in 2004, touring and occasionally releasing new material over the next decade-plus. Meanwhile, Van Halen would take a break for several years before reuniting with both Roth and Hagar at various points.

For his part, Cherone reflected happily on his tenure with the rock giants, 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 said. "You can’t take that away from me.”


The Best Song From Every Van Halen Album

See Rock’s Epic Fails: Van Halen Edition

More From Sasquatch 92.1 FM