Richie Rich #64

Harvey Comics' "Poor Little Rich Boy" is living his best life on this December 1967 cover, racing a homemade wooden go-kart — monogrammed with his signature "R" — whose wheels are actual oversized gold coins, with a red-haired friend giving chase on a scooter in the background. Warren Kremer's cover art captures Richie's gleeful, wind-swept grin perfectly, making even a neighborhood kart race feel like a million-dollar adventure. A cheerful slice of mid-1960s Harvey charm at its most fun.