The warm familiarity of holiday music has long been a boon for great stylists putting their own spin on songs that evoke nostalgia and seasonal cheer. Singular singers like Frank Sinatra, Nat “King” Cole, Ella Fitzgerald, and Eartha Kitt have left an indelible imprint on tunes we hear each December. This playlist features repertoire that conveys that classic spirit, mixing sentiment and lyric flair: a timeless soundtrack for the season.