The Serpent’s Tooth is an original Miles Davis composition released as Take 1 on the 1956 Prestige album Collectors’ Items. It was first recorded on January 30, 1953 at WOR Studios in New York with Miles Davis on trumpet, Sonny Rollins and Charlie Parker on tenor sax, Walter Bishop Jr., Percy Heath, and Philly Joe Jones. A second take was recorded on March 16, 1956 at Van Gelder Studio in Hackensack with Rollins, Tommy Flanagan, Paul Chambers, and Art Taylor. Collectors’ Items pairs two sessions and features two takes of The Serpent’s Tooth, Take 1 at about 7 minutes and Take 2 at about 6 minutes, within a jazz bebop and hard bop context. The 1953 Parker-Rollins collaboration is famous for its chaotic dynamics and Parker’s troubled period, a session that remains notable in Davis’s Prestige era before his move to Columbia in 1956.