Roamin' Thro' the Gloamin with 40,000 Headmen" (album title: "Forty Thousand Headmen"), written by Steve Winwood and Jim Capaldi, was first recorded by Traffic in 1967 or 1968. It was initially released as B-side to the "No Face, No Name, No Number" single in 1968 and also appears on their second album Traffic. Blood, Sweat & Tears also recorded it on their 1970 album, Blood, Sweat & Tears 3.
The song is sung from the perspective of the unnamed protagonist, who is only hurt, not killed, by the bullets of the eponymous headmen. The lyrics were inspired by what Capaldi refers to as "a hash fuelled dream." They have been described as being "an evocation of a dream state".
Dave Mason and Jim Capaldi's 1998-99 "40,000 Headmen" reunion tour took its name from this song.