Ruby, My Dear is a ballad composed by Thelonious Monk, written around 1945 when Monk was still developing his singular compositional voice. The piece follows a thirty-two-bar AABA form and was originally titled Manhattan Moods before Monk renamed it after Rubie Richardson, his first love and his older sister Marion's best friend, because the melodic phrase fit the name perfectly. The A sections are rooted in C major but borrow tones from C minor, creating a wistful major-minor ambiguity that gives the melody its distinctive tenderness. The bridge transposes this harmonic world up a fourth, and the composition concludes with an unexpected Db Lydian chord in the coda, a signature Monk touch that leaves the listener with a sense of unresolved beauty. The harmony features mediant relationships and what musicians have called mystery chords, including unusual voicings that blend major thirds with perfect fourths, making the changes challenging to follow by ear despite the ballad's outward simplicity. Monk first recorded the tune on October 24, 1947, during his landmark sessions for Blue Note Records, and it has since become one of the most widely performed ballads in the jazz repertoire. A lyricized version titled Dear Ruby, with words by Sally Swisher, was recorded by Carmen McRae on her 1988 album Carmen Sings Monk.
