Jazz Pepe is as old school as it gets. Opened in 1969 by the now 77 year old Okuma-san, Pepe is a basement bar that has made virtually no accommodations to the present day, making drinks there feel like you've been instantly transported back to Showa-era Japan.
The music is almost entirely jazz vocalists from Okuma-san's large collection. Okuma-san himself is a joy to talk with, open and friendly while drinking and chain smoking as if it was still 1969. Like many Shinjuku old-timers, he was quick to share stories about the old days when there were jazz bars on every corner and Shinjuku was a rough & tumble part of town.
Surprisingly for such a small, divey place, Pepe still hosts monthly live performances by some local singers. For years I had thought Pepe was out of business due to the broken door leading down to the joint and graffiti covered sign that was never lit up. Going down the stairs and finding it open was one of the best jazz experiences I've had in Japan. Photos of Jazz Pepe here at Tokyo Jazz Joints.com
Side street between the Central Hotel and K's Cinema in Shinjuku