Sam Satan. And cartoons SFW by comparison

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