Charlie's Wig is a high-energy bebop composition by Charlie Parker, written as a contrafact on the chord changes of Sigmund Romberg and Oscar Hammerstein II's When I Grow Too Old to Dream. Parker superimposed a new, intricate melody over the standard's harmonic framework, transforming a sentimental 1930s ballad into a fast, rhythmically driven bebop vehicle. The tune features dense, fast-moving melodic lines and syncopated motifs characteristic of Parker's compositional style, demanding virtuosic improvisation from its performers. It was recorded during Parker's peak bebop period in the mid-1940s, with the original session featuring a formidable lineup including Miles Davis on trumpet, J. J. Johnson on trombone, and Duke Jordan on piano. The recording later appeared on the compilation Ornithology. Within Parker's extensive catalog of original compositions, Charlie's Wig represents a deeper cut rather than one of his most ubiquitous standards like Donna Lee or Scrapple from the Apple, but it exemplifies his prolific approach to contrafact writing, in which familiar chord progressions were reimagined with fresh melodic material designed to fuel improvisation. The tune has remained in circulation through sheet music publications and is performed by bebop enthusiasts, though it has not generated the wide range of divergent reinterpretations seen with some of Parker's better-known heads. It stands as a testament to Parker's role in advancing bebop composition and expanding the jazz repertoire.