Although there’s no shortage of stellar contemporary holiday tunes, there’s nothing quite like digging into the classics—the heartstring-tugging standards that conjure rosy-cheeked Santas, perfect gingerbread cookies, and Norman Rockwell’s idyllic scenes. With its focus on old-school hits sung by some of music’s most beloved postwar vocalists, this playlist is perfect for roasting chestnuts and reminiscing about the good old days.