Top 10 Heartbreaking Holiday Covers
7. Bing Crosby & David Bowie, "Little Drummer Boy"
Keeping our morose little theme right on chugging, this song may very well have been one of the last things the legendary Bing Crosby recorded before his death in 1977. "Little Drummer Boy" isn't the best song, we readily admit -- as did Bowie, who petitioned for a different song -- but the harmonies alone more than make up for it; besides, it's Bowie and Bing on the same track. Recorded for television, no less. "Surreal" doesn't begin to describe this duet, one that makes those hackneyed studio mash-up jobs seem laughable by comparison.
6. The Carpenters, "Have Yourself a Merry Little Christmas"
"Have yourself a Merry Little Christmas" is a bittersweet song without Karen Carpenter's hauntingly beautiful vocals. Take the Carpenters' 1978 release and set it in front of the tragedy that would become Carpenter's death and legacy, this song is simply crushingly sad.
5. Death Cab for Cutie, "Christmas (Baby Please Come Home)"
Rolling Stone ranked the original Darlene Love version the greatest rock Christmas song of all time, and few artists since have been able to match Love's sheer power and sense of longing.
Reliable holiday workhorse and vocal powerhouse Mariah Carey's version falls flat, while Joey Ramone simply doesn't have the range to offer the song any emotion, odd given his strikingly beautiful take on "What a Wonderful World." Ben Gibbard's slowed-down take finally serves up "Christmas" the way it was meant to sound: Lonesome and forlorn.