When I lived in Japan, I remember wine being very expensive, except champagne, which for some reason was cheaper than in the States.
Anyway, there was this wine bar near my house, 15 min. west of Shinjuku (Chitose Karasuyama on the Keio line). It was a little 2nd-floor place, but, walking home one day, I saw a sign posted outside for the daily wine special, a 1978 Haute Medoc. Now, I'd never drunk old wine before, and this was a wine as old as I am. Being excited, I hurried up the stairs. With elation I learned the wine was only $12 a glass (1300 yen?). With sadness I learned there was none left. I must have made a sad face, b/c the salaryman next to me (who was drinking it) gave me the rest of his.
Next I tried a glass of some kind of 1976 Sauternes for like 1500 yen. In my poor Japanese, I learned that the owner had been a sommelier at some nice place and then retired to pursue his dream of owning a small wine bar serving good Italian food. He served me up some nice cheese and olives, and his cook and I were able to chat at length about the menu using a shared strong Italian food vocabulary glued up with Japanese grammar.
Here in NYC, where wine is theoretically much more popular, I tend not to find such lovingly run neighborhood wine bars serving 25 y/o wines for $15/glass. Are there many places like this in Tokyo? Maybe I should move back.