Tritone Substitution Workout — Full Cycle of Fifths

The tritone substitution is jazz harmony's most powerful tool: any dominant 7th chord can be replaced by the dominant 7th chord whose root is a tritone (diminished 5th / augmented 4th) away. G7 becomes Db7. C7 becomes F#7. The substitution works because both chords share the same tritone interval (the 3rd and 7th) — they just swap roles. The bass movement changes from a fifth down to a half-step down, creating smoother voice leading. This workout drills tritone subs through all 12 keys around the cycle of fifths. In each key, you play the original ii–V–I, then repeat it with the tritone substitution replacing the V7 chord. The total distance covered in the workout is the entire harmonic universe: all 12 major keys, 12 pairs of tritone-related dominant chords. After completing this workout you should be able to spontaneously hear a dominant chord and immediately know its tritone substitute. This is an essential skill for jazz improvisation and reharmonization.