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Answer:
LEARY
Possible Questions:
"Rescue Me" star Denis
Tripping Timothy
Denis or Timothy
Denis of "Rescue Me"
Timothy who took trips
Figure in the high '60s?
Counterculturist Timothy
Counterculture guru Timothy
Actor Denis
"Turn on, tune in, drop out" advocate
'60s guru Timothy
'60s counterculture guru
W.W. II vice admiral
Tripper Timothy
Timothy who took many trips
Timothy who preached the message found in this puzzle's theme
Timothy or Mrs. O'
Stand-up comic Dennis
Noted acid studier
LSD pioneer Timothy
LSD advocate Timothy
He went on a lot of trips in the 1960s
Harvard proponent of higher education?
Drug-culture leader in the 60's
Doctor whom Nixon called "the most dangerous man in America"
Denis who voiced smilodon Diego in the "Ice Age" series
Denis of "The Ref"
Counterculture guru
Commander of Eastern Sea Frontier: 1943–46
Comedian Denis
Big name in '60s counterculture
Author of "Turn On, Tune In, Drop Out"
Actor/comedian Denis
A U.S. vice admiral in W.W. II
60's tripper Timothy
60's guru
1960s trip taker
1960's tripper Timothy
"The Psychedelic Reader" collaborator
"The Politics of Ecstasy" author
"Rescue Me" star
"Politics of Ecstasy" author
'60s tripper Timothy
'60s counterculturist Timothy
''Turn on, tune in, drop out'' advocate