I know the dream. I've been looking for a sophisticated unpretentious "Night Club" like in the old movies for years. The Supper Club tries but you can feel the effort. The Carlyle (sp) costs a fortune and there's no dancing, same with Oak Room. The closest we've come is a couple of Latin places.
You grow up with images of the world as it was at one time but by the time you get there it's gone, and nothing real to replace it.
Those places are still around. Like Kansas City and Chicago, Indianapolis has a long history of great jazz and blues.
Wes Montgomery, Cole Porter, Hoagy Carmichael, Buddy Guy, Leroy Carr and "Scrapper" Blackwell. were all from Indiana. Indy is crossroads between a lot of larger cities so a lot of the greats have passed through.
The Chatterbox is one of those small jazz clubs. I don't think they start music til about 11 or 12 so you tend to get the hardcore music lovers not the 20-somthing faux beer swillers.
There is also one of the country's best blues clubs, The Slipery Noodle. The Noodle is also one of the country's oldest, continually operating bars. Since 1850. This place is about half a block from my office so it's also a popular lunch spot.
http://www.slipperynoodleinn.com/Index2.cfm