Deen began his career in 1983, when he joined the Portland, Oregon-based heavy-metal rock band 'Wild Dogs.' The band had been established back in 1981 and was founded by Jeff Mark, Danny Kurth, Matt McCourt, and drummer Pete Holmes.
McCourt had scouted 16-year-old Deen when Holmes and then his replacement, Jaime St. James, left the band to join 'Black 'n Blue.' The band was signed under 'Shrapnel Records.' Deen’s first big show, however, was with the musical group 'The Enemy.'
Deen performed for the self-titled debut album of 'Wild Dogs,' released in 1983. The band then released 'Man's Best Friend' in 1984 and 'Reign of Terror' in 1987. The band eventually gained popularity for Deen's drumming skills and McCourt's props at their live shows.
'Wild Dogs' vocalist McCourt was urged by 'Shrapnel Records' to find a drummer for his heavy metal band 'Dr. Mastermind,' which he had formed in 1982. He suggested Deen, who performed in the band’s self-titled debut album in 1986.
While working with 'Wild Dogs,' Deen met American guitarist and composer Tony MacAlpine. He performed in the tracks 'Autumn Lords,' 'Hundreds of Thousands,' 'Tears of Sahara,' 'The Time and the Test,' and 'The King's Cup' from Tony's second studio album, 'Maximum Security,' which was released in 1987. Deen also performed for Tony’s fifth album, 'Premonition' (1994).
The following year, he played session drums for 'Go Off!,' the second and last studio album of the heavy metal band 'Cacophony.' Deen then contributed to Marty Friedman's debut album, 'Dragon's Kiss.'
Tony introduced Deen to musician Neal Schon, with whom he eventually had a long-term artistic collaboration. Neal asked him to audition for his new hard rock/glam metal supergroup, 'Bad English,' which was formed in 1987. Deen worked as the drummer, percussionist, and also a backing vocal for the band's debut self-titled album, which was released in 1989. He also performed for its second and final studio album, 'Backlash' (1991). 'Bad English' was nominated for the “Best New Group” at the 'International Rock Awards' in 1989.
He contributed to the song 'Smoke of the Revolution' from Schon's solo album, 'Late Nite' (1989).
American guitarist Joey Tafolla roped in Deen for his second studio album, 'Infra-Red,' in 1990. He also performed for Jesus music pioneer Matthew Ward in his solo recording 'Fortress.' In 1991, he released an instructional video called 'High Performance Drumming' and later performed for the 'Boys & Girls Club of Salem.'
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Deen and Schon collaborated again in 1992, for 'Double Eclipse,' the debut album of the latter's hard rock band, 'Hardline.' He performed live for the EP 'The Hendrix Set' by two-time 'Grammy' nominee Paul Rodgers.
After working with Rodgers, Deen started doing session work with 'Grammy'-winning musician Steve Vai, who later asked him to audition for English musician Ozzy Osbourne.
In 1995, he collaborated with Osbourne on his seventh solo studio album 'Ozzmosis.’ They then toured together as part of the 'Retirement Sucks Tour.'
Following this, he did session work for producer Michael Beinhorn, recorded with 'Social Distortion,' and worked on Geezer Butler's solo project.
Deen collaborated with Vai for his EP 'Alien Love Secrets' (in the tracks 'Die to Live,' 'The Boy from Seattle,' 'Kill the Guy with the Ball,' and 'Tender Surrender') and his fourth album, 'Fire Garden' (in the tracks 'Dyin' Day,' 'Blowfish,' 'Hand on Heart,' 'Little Alligator,' 'All About Eve,' and 'Damn You').
In 1996, Deen and guitarist James Murphy collaborated for the latter's album 'Convergence.' He also contributed to 'GZR's second album, 'Black Science,' in 1997.
Deen and Murphy worked together again for the 1999 album 'Feeding the Machine.' He also contributed to 'Celebrity Skin,' the third studio album of the alternative rock band 'Hole.'
In 2001, he joined the San Francisco-based rock band 'Journey' and played for their 11th album, 'Arrival' (drummer and backing vocals), and their debut EP, 'Red 13' (drums, percussion, and backing vocals). Apart from contributing as a drummer, percussionist, and backing vocal, he also worked as a lead vocal for the tracks 'A Better Life' and the bonus track 'Never Too Late' from the band's 12th album, 'Generations.' He also played drums for the band’s next album, 'Revelation.'
In 2002, Deen collaborated with Italian singer-songwriter Vasco Rossi and played drums (live) for his 'Tracks.' They came together again in 2009, for 'Tracks 2.'
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Schon was searching for a team that could help him release his compositions that he had worked on for 'Planet US' (a short-lived supergroup with Sammy Hagar, Michael Anthony, Joe Satriani, and Schon). ‘Planet US’ had not produced an album with him. He later invited Deen, Jeff Scott Soto, and Marco Mendoza to form his new band, 'Soul SirkUS.' Based on Schon’s work that was originally composed for 'Planet US,' they recorded 11 songs for their debut album, 'World Play.'
In early 2005, 'Soul SirkUS' was ready for the promotional tour for 'World Play' (the ''Back Sleeve" version). Unfortunately, Deen fell ill and had to drop out. He was replaced by Australian drummer Virgil Donati. The ''Black Sleeve' version was the only one that had contributions by Deen.
‘Journey’ roped in Deen for the band’s 14th album, 'Eclipse,' in 2011. He played the drums and provided vocals for the self-titled debut album of the American supergroup 'Revolution Saints' in 2015. He later also contributed to the group’s second album, 'Light in the Dark.' He also worked as a drummer for the track 'Soul Hacker' from 'Genexus,' the ninth studio album by the Los Angeles-based heavy metal band 'Fear Factory.'
In August 2015, Journey fired Deen after he was booked for domestic violence. The following year, he collaborated with 'Journey' keyboardist Jonathan Cain for 'What God Wants to Hear.'
On November 4, 2017, Deen replaced drummer Brian Trichy of the Australian–American rock band 'The Dead Daisies.' Apart from playing the drums, he provided backing vocals for the band’s fourth studio album, 'Burn it Down,' which was released on April 6, 2018.
Johnny Gioeli and Deen reunited in Italy, after 25 years since 'Double Eclipse,' to start work on their collaborative debut, 'Set the World on Fire.' It released on July 13, 2018. That year, he provided the lead vocals in 'Gazing at Medusa.'
In 2019, Deen and Schon joined the 'Journey Through Time' tour, featuring the former members of 'Journey.' He collaborated as a drummer and the lead vocalist, with keyboardist Gregg Rolie. Deen also contributed to the vocals in the tracks 'Unbreakable,' 'Calling You,' and 'Live to Win' from the self-titled album of 'Restless Spirits.'