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Answer:
HEPCAT
Possible Questions:
Jazz fan
Daddy-o
Jazz aficionado
Cool dude
Jazz lover
Swinger
Jazz devotee
Jazz enthusiast
Swinger in the 40's
Swinger in the '40s
Old swinger
Jazz lover's tag
Jazz fan, maybe
Swinger, once
Swing fan
Swing aficionado of the 1940's
Space-age bachelor pad type
One who's beat but good?
One who digs your jive
Old swing digger
Old jazz buff
Jazzy swinger
Jazz performer
Jazz lover, in old slang
Dude, once
Count Basie was one
Cool one, once
Cool dude, 50's-style
1940s jazz fan
"With-it" guy of the 40's
'50s cool guy