Jon Hamm, 51, and John Slattery, 59, from Mad Men walk their dogs in The Hamptons

Jon Hamm, 51, and girlfriend Anna Osceola, 34, head out on errand run in The Hamptons

Jon Hamm packs on PDA in a black tuxedo alongside girlfriend Anna Osceola at 2022 ESPYS in LA

Mad Men at 15: how the genius advertising drama foresaw the death of the American dream