Gary Cherone sang in local bands as a teenager. In 1979, he, along with his friend and drummer Paul Geary and guitarist Matt McKay, formed Adrenalin, a hard-rock band, and performed locally. In 1981, they changed the band's name to The Dream and recorded an independent EP that consisted of six songs.
Gary and The Dream were featured in a music video produced by David Hogan, which was presented in an MTV program, ‘Basement Tapes’. The show featured music videos by unsigned artists, and The Dream's video for ‘Mutha, Don't Wanna Go to School Today,’ won the contest.
In 1985, Gary, his drummer friend Paul Geary, guitarist Nuno Bettencourt and bassist Pat Badger formed the rock band Extreme; the name was a play on the words “Ex-Dream". The foursome started writing songs and performing, and by the late 1980s, they had a large regional following.
In 1989, the band released their first self-titled album through A&M Records, which sold over 300,000 units. The band shot to fame with their second album ‘Extreme II: Pornograffiti’, released in 1990.
The album was a unique mix of hard rock, funk, and pop songs driven by Bettencourt's brilliant guitar playing. Although the album received a good reception in the rock world, its initial sales and chart success were moderate. Two singles from album—‘More Than Words’ and ‘Hole Hearted’, reached the Top 5 on the Billboard Hot 100. Two other singles ‘Decadence Dance’ and ‘Get the Funk Out’, however, received only moderate response.
In April 1992, Gary Cherone performed ‘Hammer to Fall’, a 1984 song by the British rock band Queen, along with three members of Queen at The Freddie Mercury Tribute Concert at Wembley Stadium. Extreme also performed a medley of some of Queen’s hits at the concert.
Towards the end of 1992, Extreme released their third album, ‘III Sides to Every Story’, touching new heights of creativity. It was a follow-up to their second album, and the last with the band's original members. After the release of the album, Paul Geary left the group, and was replaced by Mike Mangini.
Extreme's 1995 release, ‘Waiting for the Punchline’, was only modestly successful. After the supporting tour, guitarist Nuno Bettencourt left the group, and Extreme was officially disbanded.
In 1996, Gary Cherone was called for an audition by Van Halen, an American hard rock band formed in California. Guitarist Eddie Van Halen liked Cherone's lyrics and singing, and appointed him in November 1996 as the third lead vocalist.
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He spent the next year writing and recording a new studio album, ‘Van Halen III,’ which was released on March 17, 1998, debuting at No. 4 on the Billboard 200 chart. It sold 197,000 units in the first week, and 500,000 within a few months. However, despite a supporting tour, the album did not achieve a double platinum status as expected.
Van Halen started working on their next album, but unfortunately, Van Halen's then-record company Warner Bros. rejected the new album twice. Frustrated by the rejections, Gary left the band.
He returned to Boston and formed the band Tribe of Judah with two former members of Extreme—bassist Pat Badger and drummer Mike Mangini. They released an EP in 2001 and a full-length album in 2002. Tribe of Judah featured a more industrial/electronic sound, different from Gary’s previous works. The band also released a CD, ‘Exit Elvis’, on Spitfire Records.
In 2004, Gary Cherone reunited with Extreme and in 2007, they went on a world tour. Their new album, ‘Saudades de Rock’, was released in August 2008. It was Extreme's fifth studio album. In 2016, they released ‘Pornograffitti Live 25: Metal Meltdown’, an audio/video presentation of their 2015 concert at Las Vegas' Hard Rock Casino.
He formed a new band Hurtsmile in 2007 with his brother Mark and Joe Pessia. They released some demos on the internet, and in 2011, they released a self-titled debut album and toured to promote it.
‘Extreme,’ the first studio album of the Boston metal band Extreme, was released on March 14, 1989. The album contained four singles—‘Little Girls’, ‘Kid Ego’, ‘Mutha (Don't Wanna Go to School Today)’ and ‘Play with Me’. The songs featured catchy guitar riffs and fast soloing. Lyrically, the album represented childhood themes. The single ‘Play with Me’ was featured in the movie ‘Bill and Ted's Excellent Adventure’ and in ‘Jury Duty’.
Extreme’s second album ‘Extreme II: Pornograffiti’ as released in 1990 and was certified double platinum. The song ‘More Than Words’ was a smashing hit, and reached the no. 1 position on the Billboard Hot 100. The album's lyrics were mostly written by Gary, and were based on the concept of a fictional young boy named ‘Francis’ and his observations of a corrupt society.
Cherone’s only collaborative album with the rock band Van Halen, the album ‘Van Halen III’ was released by Warner Bros. Records, and was gold certified in the United States by RIAA. Selling over 700,000 copies as of 2011, it featured an eclectic and diverse set of songs, different from the standard arena rock.