During his teen years in Lancaster, California, Van Vliet acquired an eclectic musical taste and formed "a mutually useful but volatile" friendship with Frank Zappa, with whom he sporadically competed and collaborated. He began performing with his Captain Beefheart persona in 1964 and joined the original Magic Band in 1965. The group drew acclaim with their first album in 1967 on Buddah Records, Safe As Milk. After being dropped by two consecutive record labels, they signed to Frank Zappa's newly formed Straight Records. Zappa as producer granted Beefheart the unrestrained artistic freedom to release 1969's Trout Mask Replica, ranked fifty-eighth in Rolling Stone magazine's 2003 list of the 500 greatest albums of all time. Having not been paid for a European tour, and worn out from years of Beefheart's abusive behavior, the entire "Magic Band" left him in 1974. A brief and critically panned flirtation with more conventional rock music resulted in two albums he later disowned. Beefheart then formed a new Magic Band with a group of younger musicians and regained contemporary approval through three final albums: Shiny Beast (Bat Chain Puller) (1978), Doc at the Radar Station (1980) and Ice Cream for Crow (1982).
Van Vliet has been described as "one of modern music's true innovators" with "a singular body of work virtually unrivalled in its daring and fluid creativity". Although he achieved little commercial or mainstream critical success, he sustained a cult following as a "highly significant" and "incalculable" influence on an array of New Wave, punk,post-punk, experimental and alternative rock musicians. Known for his enigmatic personality and relationship with the public, Van Vliet made few public appearances after his retirement from music (and from his Beefheart persona) in 1982 to pursue a career in art, an interest that originated in his childhood talent for sculpture. His expressionist paintings and drawings demand high prices, and have been exhibited in several countries. Van Vliet died in 2010, after many years suffering from multiple sclerosis.