Thompson played drums with Santana in 1984 and is credited in the Beyond Appearances album along with Chester D. Thompson on keyboards. In 1992, Thompson and his family relocated to Nashville, Tennessee, after liking the area when they visited to attend noted drummer Larrie Londin's funeral. He has since played on sessions for various artists in the area, mainly in jazz, pop, and Christian music. In 1995, former Genesis guitarist Steve Hackett invited Thompson to play on his Genesis project album "Genesis Revisited". Thompson was unsure of playing on all of the tracks as initially discussed, and said "we both thought it would be too weird to do the whole album with both of us being sort of ex-Genesis people". Instead, Hackett brought on additional musicians and Thompson plays on just three tracks. In the late 1990s, Thompson began touring with jazz guitarist Denny Jiosa. In 1999, he released his first solo album, "A Joyful Noise". In 2001, Thompson toured Korea with singer and worship leader Ron Kenoly. In January 2002, Thompson performed at the debut charity gig by Collins's Little Dreams Foundation. Thompson has taught drums at Belmont University in Nashville since 1998, and has also taken classes at the university in composition and arranging. In 2008, he was "two classes away" from earning a degree. He is an adjunct instructor at its school of music. In 2008, Thompson was honoured with a Lifetime Achievement Award at the 32nd Percussive Arts Society International Convention (PASIC). In 2011, Thompson formed his jazz group, the Chester Thompson Trio, with pianist Joe Davidian and bassist Mike Rinne. They had initially played together as part of the rhythm section of the Nashville Trombone Festival which was followed by a weekly residency at the Commodore Lounge for over a year. They have released two albums: "Approved" (2013) and "Simpler Times" (2015). Thompson has endorsed Ludwig Drums (1970-March, 1977), Pearl Drums (April, 1977 - July, 1987), Sonor Drums (1990–1999) and Paiste cymbals (1970–90); he has endorsed DW Drums since 2000 and Sabian cymbals since 1990. He uses Remo drumheads, Meinl Percussion, Gibraltar racks and has his own Regaltip Chester Thompson signature drumstick. In 1980, Thompson became a Christian. He married his wife who he first met during his time playing in "The Wiz" in 1976.