From
Sir! volume 20, number 4, January 1964. Probably by
Reamer Keller.

From that same issue of
Sir!
Bill Wenzel

Jack O'Brien in
Sir! volume 21 number 2, October 1964
Charles Dennis,
Topper number 6

Also from that issue of
Topper.

All men's magazines had a comics character, this was the one for
Debonair, and it appeared in their 18th issue.
From the first issue of
Dude
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