"How I Wish" is a vocal version of Thelonious Monk's ballad "Ask Me Now," created when lyricist Jon Hendricks added words to the 1951 instrumental composition. Monk originally recorded "Ask Me Now" on July 23, 1951, during sessions for his Genius of Modern Music album on Blue Note, and the tune stands as one of his most tender and introspective ballads alongside works like "Ruby, My Dear" and "'Round Midnight." The melody blends major and minor tones to create a wistful, elusive quality, with the A section drawing primarily from one tonal center while the contrasting B section transposes up a fourth, generating subtle harmonic tension through Monk's characteristically angular phrasing and economical construction. As a contrafact built on the same harmonic and melodic foundation as "Ask Me Now," "How I Wish" preserves Monk's original musical architecture while giving it a lyrical identity suited to vocal interpretation. Carmen McRae's 1988 recording on Carmen Sings Monk served as the first and definitive vocal version, establishing the tune as a vehicle for singers and broadening its audience beyond the instrumental jazz community. Other vocalists including Mark Murphy, Karrin Allyson, and Giacomo Gates have since recorded the song. While "Ask Me Now" has appeared on landmark Monk albums such as 5 by Monk by 5 and Solo Monk, the composition remains somewhat less performed than Monk's most celebrated pieces, occupying a cherished place in his catalog as a compact, emotionally resonant ballad that rewards close listening.
