At one time Time would frequently have a drawing instead of a photograph.
These are scans rather than magazines I own. This is why I couldn't get them bigger and the borders are blurry. I wish I could.
Okay this first one doesn't count, since it's for a story specifically about comics.
April 9, 1965

May 14, 1965
by Saul Steinberg

April 4, 1967
by Paul Conrad

September 22,1967
by Gerald Scarfe

November 3,1967
these next three are by David Levine

January 5,1968

March 8, 1968

again, these next two are Gerald Scarfe.
June 26, 1968

October 11, 1968

Since these are all in chronological order, On Monday I'll be getting to Jack Davis, who did the majority of them.
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