Lesson: Learn From Jazz Great Thelonious Monk

Thelonious Sphere Monk was a brilliant jazz pianist and composer, active from the 1940s through the early ’70s. You are, presumably, an acoustic guitarist, playing music in the 21st century. As such, you may or may not be interested in classic jazz. But whatever your predilections are, there’s plenty to be learned from Monk’s unique approach to music, and much of it can be adapted for your instrument.

For example, Monk favored unconventional chord voicings, often including clusters of notes that neighbored the actual chord tones. You can do this on the guitar by using open strings in novel ways. Another common Monk tactic was to alter major or dominant chords to include a flatted fifth. If altered chords are new to you, don’t worry. There’s a little method to the madness, as you’ll see. Like a new favorite hot sauce, you may use these tangy sounds as generously or as sparingly as you like.

Another idiosyncratic aspect of Monk’s music was his approach to motivic development. He could develop any small musical idea could be developed into a much bigger, bolder statement. This is apparent in his improvisations and in many of his compositions. Since motivic development is a great musical tool—regardless of style or era—that’s where this Monk-inspired Weekly Workout course begins.

Week One

Play Ex. 1, a 12-bar blues based on Monk’s composition “Misterioso.” One interesting quirk here (as in Monk’s original) is that the melody played over the I chord (bars 1, 3, 4, 7, 8, and 11) contains the note G#. This note implies an Amaj7 chord, whereas dominant chords are by far the most typical chords used in blues. This unusual quality is one of the things that makes “Misterioso” sound like no other blues tune in the jazz canon.

Notice how the simple motif—a sixth interval, stair-stepping up and back—is used over and over through the entire piece. Some other composers may have been tempted to use more variety when writing a tune such as this, but Monk apparently found something compelling about tenacious repetition. Think about this when composing your own music. Instead of forcing something new into every measure, see how much music you can make out of one simple idea. Your twofold assignment this week: Practice Ex. 1 until you can play it smoothly at the prescribed tempo (80 bpm). Then write your own 12-bar blues—in any key—using just one motif throughout.


Beginners’ Tip

Learn to play a couple of Monk’s easier, blues-based tunes—“Misterioso” and “Blue Monk,” for example.


Week Two

Another signature sound in much of Monk’s music is the whole-tone scale—a six-note scale constructed symmetrically, using consecutive whole steps (as shown in Ex. 2a, which starts on the note B). Monk frequently peppered his compositions and improvisations with whole-tone flourishes as well as chord clusters built from the scale. Play the scale here ascending and descending a few times, doing your best to get some momentum going in both directions. Monk could—and often did—play through fragments of this scale quite briskly. Ex. 2bd illustrates some of the Monk-esque chordal sounds that can be created from the whole-tone scale in this key.

Because of the symmetrical nature of the whole-tone scale, chords built from it can be harder to name than the chords you find in conventional major-scale harmony. For instance, Ex. 2b might be considered a C#7 with an augmented 5, or A(add9) with an augmented 5, or something else altogether. Ex. 2c and 2d are equally mercurial. Generally speaking, assume that the lowest pitch is the root when naming these chords, but don’t overthink such sonorities. A little bit of mystery is fine in the whole-tone universe.

Ex. 3ad illustrate the same scale starting from C, as well as some chord clusters built from these scale tones. There are only two different whole-tone scales—one starting on B, and one starting on C. This is because the B whole-tone scale contains the exact same notes as the whole-tone scales starting on C#, D#, F, G, and A, while the C whole-tone scale contains the exact same notes as the whole-tone scales starting on D, E , F#, G#, and A#. Lots of other chord shapes can be made from the whole-tone scale, of course, and you should search for some that sound especially sweet or piquant to your ears. Since you’ll want to include one open string within each of your voicings to maximize their clustery, Monk-like character, be sure to use your open E or D strings for C whole-tone chords and your open G, A, or B for B whole-tone chords.

Beginners’ Tip

Get to know Monk’s signature tune “Round Midnight” by listening to as many different recordings as you can find.


Week Three


Monk’s music often featured major and dominant chords that he tweaked by flatting the fifth degree. (Yes, such alterations are sometimes related to whole-tone scales, but not always. Try to think of this week’s examples simply as altered chords and not as products of whole-tone harmony.) Ex. 4a is a simple chord progression with no alterations, played with basic, open-position chords.

Ex. 4b shows how much more interesting this chord progression can sound when b5 alterations are made. Try applying some b5 sounds to one of your own tunes, or to your arrangement of a cover song you enjoy playing.

While the triadic chords are fairly straightforward, such alterations may be applied to jazzier chord progressions as well, as shown in Ex. 5. Note that in each case here, the altered tone (b5) is a note from the key you’re in (C major). Hiding such colorful harmonies beneath diatonic melodies helps these chords sound more naturally integrated. Again, try applying this concept to one of your own compositions or an arrangement of a jazz standard.

Ex. 6 shows how the concepts used in Ex. 5 can be utilized in minor harmony as well. Once again, the juiciest chords here (with b5 or #5) support diatonic melody notes. This makes chords such as the B9(b5) in measure 1 sound right at home.

Beginners’ Tip

Monk rarely wrote in guitar-friendly keys, like G or D, but you can always transpose his music to suit your own level or style.



Week Four

While most of Monk’s compositions were wholly sui generis, he did write a handful of pieces that were based on popular songs of his era. “Hackensack,” for instance, employs the chord progression from George Gershwin’s “Lady Be Good.” Similarly, “Bright Mississippi” is built upon the framework of the old chestnut “Sweet Georgia Brown.” We’re not talking about copyright infringement here—Monk stole nothing. Rather, he used the chord progressions and forms from these songs as templates for his own creations.

That’s your homework this week: Choose a song, popular or not, that you like to play and write a whole new piece of guitar music based on it—keeping the original harmony and structure intact. Start simple, with something like “Goodnight, Irene” and not “Stairway to Heaven.” Throw in some Monk-inspired elements if you like—motivic repetition, chord clusters, whole-tone runs, and a b5 chord or two. If you’re not sure how to get started, check out Ex. 7, which is loosely based on “Happy Birthday.”


One final word of inspiration, which Monk himself was reported to have said to members of his band: “When you’re swinging, swing some more!”

Beginners’ Tip

Monk’s musical advice (collected by a band member) is sharp and insightful. Google Thelonious Monk advice.


Adam Levy is an itinerant guitarist and songwriter based in Los Angeles, where he is department chair of the guitar performance program at Los Angeles College of Music. His guitar work has appeared on recordings by Norah Jones, Tracy Chapman, Amos Lee, Ani DiFranco, among others. adamlevy.com.

Adam Levy
Adam Levy

Adam Levy is a first rate sideman, singer-songwriter, educator, and journalist. Check out his excellent lessons in Play Guitar Like the Great Singer-Songwriters and String Theories.

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