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For just one day every September, the spoilers become the spoiled. National Grandparents Day has been observed in the U.S. on the first Sunday after Labor Day since President Jimmy Carter signed the proclamation in 1979. But for one 6-year-old boy, long before that day was made official, every day was grandparents day.
On Aug. 29, 1955, the face of a red-haired, freckle-nosed boy named Billy Conner graced the cover of LIFE Magazine under the headline, “The Fun of Being a Grandson.” Billy lived four blocks away from his grandfather William James Conner, 63, a section foreman on the Missouri Pacific Railroad in Batesville, Ark. The photo essay by Leonard McCombe documented their afternoons reading the newspaper, eating ice cream, fishing for catfish and dealing with wiggly teeth.
Though Billy’s love for his grandfather is unmistakably genuine, his desire to spend time together stemmed, at least in part, from William’s willingness to indulge his grandson’s boyish behavior: Billy “revels in the company of granddad because he is no disciplinarian at all.”
Liz Ronk, who edited this gallery, is the Photo Editor for LIFE.com. Follow her on Twitter @lizabethronk.