Tommy Chong, who holds the record for most High Times cover appearances over the years (by a human) at eight, started that run in April 1980 with partner Cheech Marin. The pair were shown reading copies of Fortune and Money.
Then there’s the December 1978 cover featuring Truman Capote and Andy Warhol, to go along with some crazy, pot-rewritten Christmas carols. As the Warhol Museum recently reminded, the plan was initially for something a little different:
Their photo shoot took place on September 26, 1978, and is detailed in Warhol’s entry that day in his book The Andy Warhol Diaries. As he recounted later that day: “[Toni, from High Times] had a Santa costume for me and a little girl outfit for Truman. But Truman wasn’t in the mood to go into drag, he said that he was already dressed like a little boy. Truman was really drunk, hugging around.”