What with Hyde Park's recent high profile, Jimmy's (aka "The Woodlawn Tap"; don't be fooled, nobody calls it that) has been fêted by everyone from local CBS news to the New York Times. It is, for better or worse, in good times and bad, Hyde Park's neighborhood tavern. And if you can successfully dodge the undergrads on the way in, the back room is pretty excellent Sunday night music destination.
Since time immemorial, they've been hosting a Sunday evening jazz session back there. The cast of characters is ever-rotating, but the basic combo centers around Curtis Black (trumpet) and Doug Mitchell (drums), who have been at this for longer than anyone really knows. Their tastes run to pretty classic stuff: think Sonny Rollins, Monk, '50s and early '60s style Miles Davis, etc. The musicians are different every night, but you're usually in for good guest spots on sax, keys, and guitar, particularly in the second set, when the band stretches out a bit. The acoustics aren't great, but the dark-room-and-stiff-drinks factor is not to be underestimated. The music starts around 9pm (there's usually a blues session earlier in the afternoon) and there's no cover, but it's good form to drop something in the tip jar when it comes your way. Jimmy's is at 1172 E. 55th St., at Woodlawn.