110. "Travelin' Soldier," The Dixie Chicks (1996)
This is just one of those songs it's impossible to deny-the entire story, told from young love to the tragedy of war is impossibly honest and recalls Dion's "Abraham, Martin, and John" in many ways. Plus, I cannot get enough of the wonderful creatures that are the Dixie Chicks-every year I light a candle hoping for their return to the studio.
109. "On the Road Again," Willie Nelson (1980)
Nelson's anthem is at first so catchy with the consistent bouncing rhythm that drives every verse and chorus-the song literally sounds like you're bound on the road, going places that you've never been. I love the way that Willie would bring the chorus back almost as if he was making a turn, that minute delay in getting back into the song-it's these creative touches that make the Red-Headed Stranger one of my favorite performers.
108. "You Were Meant for Me," Jewel (1996)
I will admit that when Jewel lost her Best New Artist trophy at the Grammys to LeAnn Rimes I was a little bit giddy-Rimes had that Patsy Cline charm and was singing one of Cline's songs ("Blue"), and man could that girl belt (I used to sing that song all around my house), but in the years since it's Jewel that has become my preferred, particularly in this song about a woman convincing herself that happiness is fate, even if reality doesn't seem to agree.
107. "Without You," Mariah Carey (1994)
I have never loved Mariah Carey. The diva-to-worship thing didn't seem to click with her, and I always felt she seemed like a truly awful and stuck-up person in real life. That being said, the woman could sing better than most any chanteuse of her era, and I particularly loved this Harry Nilsson remake, which allows her to get a little bit deeper into her register.
106. "Ziggy Stardust," David Bowie (1971)
How can you not love a song that's about a random magical guitar player (part Jimmi Hendrix, part Flash Gordon), who plays with the spiders from Mars and is apparently well-hung (seriously, that's a lyric in this classic). Bowie's songs have always had so much electricity to me, and I love the way you don't quite know what direction he's about to go.
105. "Stardust," Nat King Cole (1956)
Yes, I'm aware I went back-to-back Stardust (that was a complete accident I didn't notice til I started listening to this playlist). Seriously, though-of all of the musical moments in Sleepless in Seattle, this one feels the most heartfelt and distant. I have watched this movie more times than I can count, and every time Cole's voice comes out and says, "the melody haunts my reverie" I can't help but swoon just a little bit longer.
104. "Can't Help Falling in Love With You," Elvis Presley (1961)
And here we come to my favorite song from the King. The song is schmaltzy, but Elvis's voice is just so melodic and so forthright that I don't even care. I used to play this song (which was part of my very first mixed CD) over and over and over again in my basement with all of the lights off, just sort of basking in the opening lyrics, imagining my prince would come.
103. "9 to 5," Dolly Parton (1980)
When I was considerably older and realized that 9-5 was actually a relatively short workday by modern practices, I would occasionally sing when no one was around and I was working super late "working 7 to 10" or some such version. Such is the fun of Dolly's rambunctious, only-country-in-terms-of-accent pop ditty about the routine of going into the office each-and-every day.
102. "Cigarettes and Chocolate Milk," Rufus Wainwright (2001)
Rufus Wainwright was someone that I discovered in college. I was just starting to realize that finding gay boys cute had a lot more rewards than finding straight boys attractive, and so I sought out openly gay singers (a relatively short list then and now). Wainwright, with his Judy Garland love and his passionate, Joni Mitchell-style lyrics seemed the most appropriate match.
101. "Hurt," Johnny Cash (2002)
Wow-I am still floored to this day by the first time I heard this song. Cash's voice while tackling a Nine Inch Nails classic was absolutely brutal-it felt like a weird jolt to think about this song not from the perspective of a young rocker but from an aging icon-it may be one of the most original re-imaginings of a song I've ever heard.
And there you have it folks-the halfway point in our countdown. We've still got 100 songs to go-who are you hoping for in the top half? And what singer means Christmas the most for you? Share your thoughts in the comments!