Cootie Williams and His Orchestra 1941–1944 is a compilation album of recordings by jazz trumpeter Cootie Williams from 1941, 1942, and 1944 (no recordings were made in 1943 due to the 1942–44 musicians' strike).

The April 1, 1942, session includes the first recording of "Epistrophy" (titled "Fly Right" here), written by Thelonious Monk, Kenny Clarke, and Cootie Williams[3] earlier the same year.

The August 22, 1944, session includes the first recording of Monk's "'Round Midnight".

The January 4, 1944, session marks the recording debut of Bud Powell, then aged 20.

[4] The January 6, 1944, session features two of Pearl Bailey's earliest recordings.