“Ruby, My Dear” is a ballad by Thelonious Monk, first recorded in 1947. It’s one of Monk’s most lyrical compositions, and the 1957 recording with John Coltrane is especially celebrated.
The form is a 32-bar AABA. The harmony is full of ii-V progressions that move chromatically and into distant keys, with Monk’s characteristic dissonances. The melody is tender yet unpredictable.
For improvisation, stay close to the melody and outline each ii-V clearly. Use space and Monk-style voicings if you’re a pianist.
Practice slowly, learning the chord changes thoroughly. Listen to Monk’s solo piano versions.
Section by section: the A sections move through ii-V progressions that drift chromatically, so practice each ii-V separately and listen for where it resolves. Monk often substituted unexpected chords, so check your lead sheet against his recordings. In the bridge, the harmony moves to a new key center before sliding back; target the new tonic’s third to make the shift clear. Because it’s a ballad, think about each note’s weight and placement, and use Monk-style touches: a minor second cluster, a pause, a repeated note.
Practice tip: learn the melody exactly as Monk plays it, including the rhythmic quirks, before you improvise. Then try playing the melody with only small embellishments for a whole chorus; Monk himself often stayed close to his themes, and that approach suits this tune beautifully.
Using the Ruby My Dear Lead Sheet PDF on gigs: keep a concert-pitch copy and a copy in your instrument’s key, label the intro and ending on the page, and note the tempo and feel the band usually plays. Small notes like these keep you calm when a tune gets called on the spot.
Is it hard to play? It’s intermediate to advanced. Recordings to study: Monk with Coltrane and Monk’s solo versions. Learn more about the composer on Thelonious Monk’s Wikipedia page, and find more ballads on Minedit.