"Bob Drake was born in Cleveland, Ohio on December 6, 1957, and spent his youth in Watseka, Illinois. There he taught himself how to play guitar and drums, but after hearing Yes's Fragile in 1972, Drake decided he wanted to be a bassist and bought himself a Rickenbacker 4001 bass guitar, which he still uses today. Henry Cow also had a big influence on him: "[T]hey were doing something I felt was a lot closer to what I was imagining I'd like to do - 'complex' intricate songs and arrangements, noisy things going on which fit organically in the music, and less emphasis on 'perfect' studio overcooked impersonal perfection."

Drake experimented with recording techniques and "warped rock", but soon found that no one was interested in "new and strange music" in his rural Midwestern home town. He moved to Denver, Colorado in 1978 where he worked for a while as a sound engineer on B horror movie sets. He also spent time recording local underground bands and playing bass guitar and drums with some of them. Drake put an advertisement at a local music store requesting a guitar player "into Henry Cow, Yes ...", and met up with experimental rock guitarist and composer Mike Johnson. Drake and Johnson played in a few cover bands before forming Thinking Plague in 1982. By 1990 Thinking Plague had recorded three albums and established a name for themselves in progressive circles.

In the late 1980s the Denver music scene "just evaporated" as musicians seeking "greener pastures" moved elsewhere. Drake, "flat broke" at the time, moved to Los Angeles where he found a job as a recording engineer. There he established a name for himself working with several mainstream artists like Ice Cube, Tina Turner and Engelbert Humperdinck. During this time he also formed an alternative rock group, Hail with ex-Thinking Plague's singer Susanne Lewis, and joined Dave Kerman's avant rock group, the 5uu's. Hunger's Teeth, the 5uu's' third album was praised for its "challenging music" and "production values", and made Drake a "sought-after engineer and collaborator".

Drake released his first solo album, What Day is It? in 1994. It was a limited edition (1,000 copies) self released record that Drake pressed himself. He later made five more solo albums, which were all released on ex-Henry Cow drummer Chris Cutler's UK independent record label, Recommended Records. In 1994 Drake and Kerman moved to an old farm house owned by Cutler and Henry Cow's sound engineer EM (Maggie) Thomas in Caudeval, southern France. They converted it into a studio which they called Studio Midi-Pyrenees. Later Drake worked closely with Cutler on a number of projects for Recommended Records, including the remastering of several albums and box sets, for example The Art Box (2004) and The 40th Anniversary Henry Cow Box Set (2009). He also joined Cutler's avant-rock band The Science Group in 1997, in which he played and engineered/produced the group's two albums.

Drake continued to work on and off in the 2000s with Thinking Plague and the 5uu's. In 2007 he formed his own group, Bob Drake's Cabinet of Curiosities to perform material from his solo albums live on stage. The group comprised Drake (guitar, vocals, violin, banjo), Kerman (drums), David Campbell (guitar, bass guitar, vocals) and Jason DuMars (soprano/alto saxophones, keyboards). They played at NEARfest in Pennsylvania in June 2007 with guests Olivier Tejedor (keyboards) and Lynnette Shelley (vocals)."