Crazy He Calls Me is a 1949 song with music by Carl Sigman and lyrics by Bob Russell, first recorded by Billie Holiday with Gordon Jenkins and His Orchestra for Decca Records. The composition is a tender jazz ballad built on a flowing, introspective melody that conveys deep romantic devotion, with the singer embracing the label of crazy as a willing consequence of love's hold. Russell's lyric unfolds with a quiet intensity, cataloging the irrational lengths to which devotion drives the narrator, while Sigman's melody supports the sentiment with warm, sophisticated harmonic movement. Holiday's original recording established the song's emotional template, her voice conveying vulnerability and conviction in equal measure, and it quickly entered the standard repertoire. Peggy Lee recorded a version for Capitol Records the same year, bringing a cooler, more intimate swing feel to the material. The song emerged during Sigman's prolific postwar period, following his collaboration with Russell on the hit Ballerina and preceding later successes like It's All in the Game. Among subsequent interpreters, Dinah Washington's 1954 live recording with Clifford Brown added a brasher jazz edge, while Sam Cooke's 1959 rendition on his Tribute to the Lady album reframed the song through a soulful lens. The composition has proven remarkably adaptable, attracting performances from Frank Sinatra and Ella Fitzgerald among many others, and it remains a widely performed standard valued for its emotional directness and melodic warmth.