A Guide To Help You Play Better Jazz Piano

Ron Drotos

History and overview:
After “Round Midnight,” “Ruby, My Dear” may be the most famous ballad by Thelonious Monk. In any case, it’s very well known and while not every jazz musicians has it memorized, it’s an important tune to learn and play with your musical peers.

Monk was a master at writing ballads, and the chords are just “off-center” enough to give you some real challenges and make you improvise in different ways. It seems like just when we think we know where one of Monk’s chord progressions is heading, he throws in something unusual that sounds wonderful in his unique way!

Monk first recorded “Ruby, My Dear” in 1947, right at the height of the bebop era, and continued to perform it throughout his whole career.

Recommended videos/recordings:
(for international readers who may not have access to these YouTube links, I’ve indicated the original album names wherever possible so you can listen to them on music streaming services, etc.)

Thelonious Monk: Solo Monk

Thelonious Monk: With John Coltrane

Bud Powell: A Portrait Of Thelonious

Musical ideas and jazz piano practice tips:
“Ruby, My Dear” is a rare instance where The Real Book provides some of the left hand rhythms for a piano arrangement. In the first measure, you hold each chord for a half note. And then, in measure 2, each note of the rhythm corresponds to an individual chord. Monk wrote a lot of chromatic passing chords here and they need to played in this exact rhythm. (The half notes in m. 1 are optional, but will help you approximate Monk’s “sound.” A stride LH also works well in m. 1 if you want to do something different.)

The harmonies in “Ruby, My Dear” are pure Monk, and the turnaround in m.7-8 is probably unique in the history of jazz and popular song.

In a piece like this, there’s a big question of how to improvise over it or even whether you should solo at all. Monk’s pieces are a true marriage of harmony and melody and while the chords sound exactly “right” under the melody, it can be tricky to make sense of them on their own. Even some of Monk’s sidemen struggled to solo over his tunes!

Even Monk himself didn’t always take fully-improvised solos on his tunes. He often was happy embellishing and playing variations on the melody during his “solos.” While it’s definitely possible to play a coherent and musical solo over the “Ruby, My Dear” chords, it would also sound great to simply play around with the melody and have fun with that. Try both approaches and see which works best for you.

Enjoy the journey, and “let the music flow!”

Further links and resources:

Here's why Thelonious Monk's music is so hard to play

The Best Way To Use The Real Book

8 ways Thelonious Monk was influenced by Art Tatum

How To Learn Jazz Piano
A podcast to help you learn jazz piano more effectively

Take a Free Jazz Piano Lesson

Mastering The Real Book: A 10-week Skype Intensive for Jazz Pianists

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