'The Christmas Song (Chestnuts Roasting on an Open Fire)'
The best: Nat King Cole (from "The Christmas Song")
The crustiest of crusty old holiday classics, “The Christmas Song” was written in 1944 by crooner Mel Tormé, and to this day, it should really only be tackled by fellow jazz crooners like Cole. Cole actually recorded two versions of the song in 1946, but it's the second one, with its cinematic string section, that's become an enduring classic—and our readers' favorite. Originally subtitled "Merry Christmas to You," Cole's version expresses the song's simple sentiment with an elegance that few have equaled since.
The worst: Stevie Wonder and Indie.Arie (available on some copies of "Voyage to India" and as part of "The Complete Stevie Wonder" from iTunes)
Not to be confused with Stevie’s perfectly acceptable solo version, which appears on his album “Someday at Christmas,” this ridiculous, lounge-act duet was recorded for a Target commercial in 2002. It has the dubious distinction of being the first song created for an advertising campaign to be nominated for a Grammy, but it lost to the Michelle Branch/Santana duet “The Game of Love.” (Keeping a Target commercial from winning a Grammy might go down as Branch’s greatest contribution to popular music.)
Also performed by: The Supremes, the Jackson 5, Tony Bennett, Luther Vandross, Andy Williams, Barbra Streisand, Bob Dylan, New Found Glory, Céline Dion, Clay Aiken, Dwight Yoakam, James Taylor, Jessica Simpson, Hootie & the Blowfish, Kenny Loggins, Martina McBride, New Kids on the Block, *NSYNC, Reba McEntire, Mary J. Blige.