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, which performed locally.

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.

[1] 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.

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.

Cherone's career came full circle in April 1992 when he performed "Hammer to Fall" onstage with the three surviving members of Queen at The Freddie Mercury Tribute Concert at Wembley Stadium.

[4] Cherone was afraid that he would be rejected by the Van Halen fan base and urged his bandmates to not limit the set list to songs recorded with their current lead vocalist, as they had done when Hagar joined the group.

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 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.

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 ex-Dream Theater drummer Mike Portnoy, featuring Paul Gilbert on guitar and Billy Sheehan on bass.

Since 2004 Extreme have re-united with Cherone on several occasions for "one off" shows in their home town and in New England, but in November 2007 they announced plans to do another world tour along with a new album.

In 2016, the band released Pornograffitti Live 25: Metal Meltdown, an audio/video presentation of its 2015 concert at Las Vegas' Hard Rock Casino.

"[13] In June 1999 and again in January 2001, Cherone famously wrote a pair of open letters to Eddie Vedder in response to the latter’s support for the pro-choice movement.