Gary Francis Caine Cherone grew up in Malden, Massachusetts (the third of five brothers and the younger of fraternal twin Greg Cherone). Raised in a middle-class Catholic family, Cherone was quiet, creative, and athletic. As a youth he dreamed of a career as a basketball player until he suffered a serious knee injury.

In his teenage years, Cherone turned to singing in local bands and was heavily influenced by the reigning rock frontmen of the day, most notably Roger Daltrey of The Who, Steven Tyler of Aerosmith, and Queen's Freddie Mercury.

In 1979 Cherone and drummer friend Paul Geary along with guitarist Matt McKay, formed a hard-rock band called Adrenalin and performed locally.

In 1981, they changed the band's name to The Dream and recorded a six-song independent vinyl E.P.

A few years later, Cherone and The Dream appeared on the early MTV program Basement Tapes, a show in which the viewing audience "voted" (via toll-free telephone number) for one of two competing amateur music videos submitted by unsigned artists. The Dream's video for "Mutha, Don't Wanna Go to School Today," won their contest, beating a then-unknown Henry Lee Summer by just 1% of the total vote... incidentally, both Cherone and Summer had once had aspirations of playing basketball as a career.

In 1985, Cherone and Geary met guitarist Nuno Bettencourt and bassist Pat Badger in an altercation over a dressing room, but the rivals soon became collaborators and shortly after the combined foursome took the name Extreme, and began writing their own material.

By the late 1980s, the group had attracted a large regional following; in 1987, the band signed with A&M Records, which released their self-titled debut album in 1989. Selling over 250,000 copies, the band's debut album justified a second, and in 1990 the band recorded the critically-acclaimed Extreme II: Pornograffiti, a fiery mix of hard rock, funk, and pop propelled by Bettencourt's extraordinary guitar playing. The album's lyrical content, mostly written by Cherone, was loosely based on the concept of a fictional young boy named "Francis" and his observations of a decadent, corrupt, and misogynistic society.

Although well-received by the rock world in the press, initial sales and chart success for the album were sluggish until A&M released the acoustic ballad "More Than Words" in the early spring of 1991. The song was picked up by mainstream radio and became a huge smash, reaching #1 on the Billboard Hot 100 that summer. Extreme II: Pornograffiti was eventually certified quadruple platinum and remains a notable entry in the genre (also in 1991, Extreme toured in support of David Lee Roth).

Cherone's career came full circle in April 1992 when he performed "Hammer to Fall" onstage with the three surviving members of Queen in The Freddie Mercury Tribute Concert at Wembley Stadium. (Extreme also performed a medley of Queen hits earlier in the day).

Later that year, Extreme released III Sides To Every Story, a concept album known by the band as their finest work. This album marked the pinnacle of the band's creative ability as a whole.

As the decade progressed, the sudden popularity of grunge brought about a sea change in the pop music industry. In response, Extreme's 1995 recording, Waiting for the Punchline, was a stripped-down and cynical affair that was only modestly successful. After the supporting tour, Bettencourt became dissatisfied and left the group to launch a solo career (Extreme officially folded almost immediately afterward).

In the fall of 1996, after a falling out with vocalist Sammy Hagar and a failed reconciliation with founding vocalist David Lee Roth, arena rock superstars Van Halen found themselves without a singer and called on Cherone (who shared the band's management) for an audition.

Guitarist Eddie Van Halen liked Cherone's work ethic and soon named Cherone as the band's third (and as the guitarist would often comment, "final" ) vocalist. Cherone took up residence in Van Halen's guest house and spent the next year writing and recording a studio album. Released on March 17, 1998, Van Halen III was an eclectic and diverse set that marked a departure from Van Halen's straightforward rock sound.

Neither the album nor the supporting tour performed to expectations (III was the first album in the band's career to not achieve at least double platinum status).

The tour brought back many older Van Halen songs that fans had wanted to hear for years. This was largely because Sammy Hagar refused to play all but the most famous of Roth-era songs. Unlike the band's subsequent 2004 and 2007 tours (the only ones to date since the III tour), Van Halen toured outside of North America in 1998, playing dates in Japan, Australia, New Zealand, and Europe as well.

Plans progressed for a follow up album by the end of 1999. Releasing a new studio album a year after the previous one had not been done by Van Halen since 1982 and the release of Diver Down.

In November 1999, after spending the year attempting to record III's follow-up, the band issued a press release announcing Cherone's amicable departure. Since then, Cherone has remained on good terms with his former bandmates, and has gone on record numerous times with his thoughts on why the collaboration didn't particularly work.

After his departure from Van Halen, Cherone returned to Boston and put together a new project, Tribe of Judah. The band played several shows in the Boston area and released a CD on Spitfire Records entitled Exit Elvis.

He has on occasion guested with Sammy Hagar and Michael Anthony during their The Other Half performances, and Nuno Bettencourt's recent projects, as well as with the Boston Rock Opera.

In February of 2003, just one week after The Station Nightclub Fire, Gary and his brother, Markus, performed "More Than Words" during a memorial service for the victims. The memorial was broadcast live on WHJY in Providence, RI.

In 2005, Cherone released a four song sampler CD, Need I Say More that was written and produced by Steve Catizone and Leo Mellace. This album was recorded by Jeff Yurek at Sanctum Sound in Boston, Massachusetts and mixed by Carl Nappa in New York City. Musicians including Dave DiCenso (drums), Baron Browne (bass) and Steve Hunt (keyboards) are also featured on the record.

In May 2006, Cherone sang in three shows as part of Amazing Journey, a tribute to The Who created by Dream Theater drummer Mike Portnoy, featuring Paul Gilbert on guitar and Billy Sheehan on bass. Not long after, Gary and his brother Markus Cherone created their own tribute to The Who, Slip Kid. Presently the band continues to perform regularly in the Greater Boston area.

Later that year, Van Halen was inducted into the Rock and Roll Hall of Fame. Cherone's two-year stint with the group did not establish him as a band member eligible for induction. However, at the televised induction ceremony, the group's bassist Michael Anthony thanked Cherone for his contributions.