The Very Best of Thelonious Monk includes ten tracks recorded between 1954 and 1957, mostly for Prestige and Riverside, but with one track from Thelonious Monk with John Coltrane, a 1957 album on Jazzland, a Riverside subsidiary label.
The sessions in this period, most of which were also produced by Keepnews, start after Monk's obscure beginnings on Blue Note but predate his rise to fame on Columbia. The Prestige and Riverside dates capture the moment when, as Tesser tells us, he "began to earn the credit he deserved, as a bandleader, composer, and bebop innovator. He worked with a fairly wide roster of famous collaborators - among them trumpeters Thad Jones and Clark Terry, saxists Sonny Rollins and Coleman Hawkins, bassists Oscar Pettiford and Wilbur Ware, and three of bebop's foundational drummers in Art Blakey, Roy Haynes, and Max Roach - and recorded in contexts ranging from unaccompanied piano to a ten-piece orchestra. It was clearly the most productive segment of his career."
Although this collection primarily focuses on Monk's compositions, which include such all-time classics as "Blue Monk," "Ruby, My Dear," and "'Round Midnight," it also includes selections from his first two Riverside albums that sought to present a more accessible Thelonious Monk to the public. "One of many things that I love about the Thelonious Monk Plays Duke Ellington and The Unique Thelonious Monk albums - both of which featured Monk covering other artists' compositions - was that each song he played sounded like it could have been written by him," says Phillips. "He had a very distinctive approach to playing the piano and a rhythmic, harmonic, and melodic vocabulary all his own. So even when he played an Ellington tune or an old standard like ‘Honeysuckle Rose,' it still sounded uniquely like Thelonious Monk."