As the ’50s drew to a close, so did Thelonious Monk’s illustrious tenure on Riverside Records. In fact, the three dates needed for this title would be his penultimate for the label. The concept of the album consists of five Monk originals performed in a quintet setting. Ironically, this was the first time that Monk had recorded with a lineup that so prominently featured the “standard” bop rhythm section incorporating both a trumpet (or, in this case, cornet) and sax player. The quintet featured on Five by Monk by Five includes Monk (piano), Thad Jones (cornet), Charlie Rouse (tenor sax), Sam Jones (bass), and Art Taylor (drums). Rouse would become Monk’s permanent tenor saxophonist for the majority of the 1960s. In what had become somewhat of a tradition, the disc’s program consists of several of Monk’s more established works as well as a few new compositions. One of the new works, “Jackie-ing” (incidentally, named after one of Monk’s nieces), leads off the disc. It exemplifies the loose, disjointed, and exceedingly difficult arrangements that would define Monk as a premier composer/arranger/bandleader. This is in contrast to Monk the keyboard player and band member, which he skilfully demonstrates throughout the track as well as the rest of the album. The song’s opening jam features a tasty tug of war between Rouse’s animated lead and Monk’s interjections and piano antics. Jones’ cornet is incorporated tastefully throughout Monk’s tricky arrangements. The stark contrast in performance timbre between the comparatively subdued Rouse or Monk and the frenetic bleating of Jones is notably disconcerting. The CD reissue includes two alternate takes of “Played Twice,” the other Monk composition to be debuted on Five by Monk by Five. – Lindsay Planer