Monk → Coltrane → Mingus → Ornette is the shortest route to experience

 Monk → Coltrane → Mingus → Ornette is the shortest route to experience, in 60–90 minutes, how post-bop jazz expands step by step from “design → inquiry → construction → liberation.” Monk, on Brilliant Corners and Monk’s Music, lays out the blueprint of ma (charged silence), surprise harmonies, and springy rhythm, distilled in “’Round Midnight” and “Epistrophy.” Coltrane, through Giant Steps, My Favorite Things, and A Love Supreme, pushes from ferocious chord cycles to modal playing and spiritual song; “Naima” and “Acknowledgement” mark the transformation. Mingus, on Mingus Ah Um and The Black Saint and the Sinner Lady, builds a vast narrative out of composition/arrangement drama and a blues/gospel foundation; “Goodbye Pork Pie Hat” and “II: Prayer…” are key points. Ornette, on The Shape of Jazz to Come and Free Jazz, releases harmony’s constraints and advances melody-led harmolodics; “Lonely Woman” is emblematic. For bridges: Monk’s “Epistrophy” → Coltrane’s “Giant Steps” highlights bold rhythm and harmony; Coltrane’s “Naima” → Mingus’s “Goodbye Pork Pie Hat” traces lyricism and deep blues; Mingus (with Dolphy) → Ornette’s “Lonely Woman” captures the leap in ensemble freedom. In short—learn the skeleton with Monk, expand with Coltrane, narrativize with Mingus, and shed gravity with Ornette.