Bob DeBoo, a contributor to Upright Citizens, joins Adam Maness to explore their favorite live albums from the legendary Village Vanguard jazz club. They reminisce about the venue's unique acoustics and intimate atmosphere while discussing the groundbreaking performances of jazz legends like Sonny Rollins and Bill Evans. The duo also delves into the exhilarating dynamics of live sessions, the evolution of John Coltrane’s sound, and the improvisational brilliance of musicians like Joshua Redman, capturing the vibrant spirit of jazz.