By Tanner Stransky
December 25, 2008 at 12:00 PM EST

Every holiday season, I weep quiet tears when I listen to Judy Garland’s “Have Yourself a Merry Little Christmas.” And yet every holiday season, I put myself through the agony–and ecstasy–of it approximately 4,294 times. Guess I enjoy some pain during an otherwise jolly time of the year. The video of the song–with Garland performing it during her role in Meet Me in St. Louis–is just as haunting. She sings it while wearing both a wonderfully sparkly head scarf and the saddest look of all time. Play that, music box, Judy, just play it…

PopWatchers, weigh in: Is this the most tragic Christmas carol of all time? Do you weep when listening? Or does it make you feel hopeful for the future?

More from EW:
‘Have Yourself a Merry Little Christmas’: The history of a popular song
Bah, Humbug: The 100 Greatest Down-and-Out-on-Christmas Songs
The Yulies: Celebrating the Christmas TV-movie genre