It's Ian's birthday (soon)! So he's running the dang podcast!!! For his Birthday Boy's Choice picks, he lands on two classic-adjacent tunes from years not yet covered on the show. "Happy Holidays" by Bing Crosby (with the Music Maid and Hal and John Scott Trotter and His Orchestra) seems like a commercial for hotels masquerading as a Christmas song, but it's actually a stealth New Year's song masquerading as musical theatre masquerading as a Christmas song. "Winter Weather" by Benny Goodman (with vocals by Peggy Lee and Art Lund) is a refreshing clarinet-heavy palate cleanser.

The ranking music in this episode is the medley from history's greatest film, Muppet Family Christmas.