2014: Well, what can one say, really? There are just so many Christmas songs, most of which have been performed by countless artists. Some of them for centuries. Part of me wants to make some kind of comprehensive list of every Christmas song I've ever heard, and which artists have sung them. But that would be... just overwhelming (probably impossible). I suppose I could just try to say a bit about some of my favorites. I can't really say with any certainty that I actually have one true favorite, because there are so many songs that I love. But I do usually like to say that my favorite is "Christmas Wrapping" by The Waitresses. I even had that as a ringtone one holiday season several years ago.
I think probably the first Christmas album I ever owned was by Nat King Cole. I had that on cassette tape, and I might still have it around here somewhere... or I might not. I don't recall if I ever had any other Christmas albums on cassette, but I've got a bunch of Christmas CDs, and still occasionally get new ones. (I have a number of them on my Amazon wish list.) Also I have acquired numerous Christmas mp3s over the years. Most of those I got from Amazon, either buying them or getting them for free during the site's annual holiday giveaway of mp3s (which normally happens Advent calendar-style). But the year I started this page (2014), Amazon stopped doing that, which made me kind of sad, because I had come to see it as a tradition, over the past few years. I didn't always take all the freebies they were offering, but I listened to all of the samples, and downloaded the ones that interested me. This year, however, the only thing they seem to have is a playlist called "All Is Bright" (edit: no longer available), which you can get for free if you're an Amazon Prime member, but I'm not. So... I could buy any of the songs if I wanted them, but I don't think I will. Anyway... I don't really know what else to say right now. But I've put together a Spotify playlist for your listening pleasure.
2015: Last year, I started making a playlist on YouTube with a few Christmas songs... but I didn't add the list to this page until this year, when I added a bunch more songs to that playlist. (There's some crossover between the Spotify and YouTube lists.) Also this year, Amazon is once again only offering a holiday playlist for their Prime members, called "Indie for the Holidays" (edit: no longer available). I listened to the samples, and only decided to buy one song, "Winter Time," which I think is really nice, but I don't really think of it as Christmas-y at all, and barely even wintry. I also decided to download a few tracks from last year's Amazon playlist: "Ho Ho Ho", "O Come All Ye Faithful", and "The Angel Gabriel". And actually there were some other good songs. I also downloaded some other random Christmas songs that aren't on that playlist.
YouTube playlist: Merry Christmas from the Family by Jill Sobule (1995), What's This from The Nightmare Before Christmas (1993), Merry Xmas Everybody by Slade (1973), Santa Claus Is Comin' to Town by Bruce Springsteen (1978), Jingle Bell Rock by Hall & Oates (1983), Last Christmas by Wham! (1984), Hey Santa! by Carnie & Wendy Wilson (1993), Joy to the World by Bruce Cockburn (1993), What Child Is This? by Vanessa Williams (1992), Santa Baby by Rev Run ft. Ma$e, Puff Daddy, Snoop Dogg, Salt N Pepa, Onyx & Keith Murray (1997), Omedetou Christmas by Sailor Moon cast (Japanese; 1995), Frosty the Snowman by Cocteau Twins (1993), I Want a Hippopotamus for Christmas by Gayla Peevey (1953), Please Come Home for Christmas by Charles Brown (1960), Toy Packaging by Sara Groves (2008), Ding Dong Merrily on High by Jackie Evancho (2011), Father Christmas by the Kinks (1977), Xmas at Kmart by Root Boy Slim (1978), Let It Snow by Luscious Jackson (1999), All I Want for Christmas Is You by Mariah Carey (1994), Season's Freaklings by Bunnygrunt (1996), Christmas Wrapping by the Waitresses (1981), Oi to the World by No Doubt (1997), Carol of the Bells by Pentatonix (2012), Where Are You Christmas? by Faith Hill (2000), It's the Most Wonderful Time of the Year by Martina Sorbara (2003), Greatest Time of Year by Aly & AJ (2006), Marshmallow World by Francesca Battistelli (2012), Christmas Time Is Here by Leftover Cuties (2012), The Holly and the Ivy by Mediaeval Baebes (2003), Little Drummer Boy by Pentatonix (2013), Jingle Bells by Rainbow Dash (2015), A Holiday Song by Lisa Loeb (2013), Text Me Merry Christmas by Straight No Chaser ft. Kristen Bell (2014), Someday at Christmas by Stevie Wonder (1967), Mary, Did You Know? by Pentatonix (2014), Christmas Eve/Sarajevo by Trans-Siberian Orchestra (1996), Winter Wonderland by Doris Day (1964), Christmas the Whole Year Round by Sabrina Carpenter (2015), Dear Santa by Girls' Generation-TTS (2015), Do You Hear What I Hear? by Home Free (2014), Sleigh Ride by Karmin (2012), Joy to the World by Pentatonix (2015), Baby It's Cold Outside by Idina Menzel and Micheal Bublé (2014), Santa Tell Me by Ariana Grande (2014), Let It Snow by Jean-Luc Picard & crew (2013), Silent Night by Chewbacca (1999/2016), The Wexford Carol by Yo-Yo Ma ft. Alison Krauss (2008), Good King Wenceslas by Loreena McKennitt (1995), White Wine in the Sun by Tim Minchin (2009), God Rest Ye Merry Gentlemen by Annie Lennox (2010), Have Yourself a Merry Little Christmas by Ingrid Michaelson (2017), You Make It Feel Like Christmas by Gwen Stefani ft. Blake Shelton (2017), Christmas C'mon by Lindsey Stirling ft. Becky G (2017), Santa's Coming for Us by Sia (2017), The 12 Days of Christmas by Straight No Chaser (1998), Socks by JD McPherson (2018), Making Christmas by Pentatonix (2018), All I Want for Christmas Is You by Ingrid Michaelson feat. Leslie Odom Jr. (2018), Don't Start Without Me by The Fizz (2018), You're a Mean One, Mr. Grinch by Lindsey Stirling feat. Sabrina Carpenter (2017), Christmas Every Day by David Archuleta (2018), The Christmas Song by Lauren Daigle (2018), Rudolph the Red-Nosed Reindeer by William Shatner feat. Billy Gibbons (2018), Joy to the World by Shameik Moore (2018), Santa Claus is Coming to Town by Broken Peach (2016), Loneliest Time of Year by Mabel (2019), Christmas Valentine by Ingrid Michaelson and Jason Mraz (2019), December Daze by Janet Devlin (2015), Make It to Christmas by Alessia Cara (2019), Must Be Santa by Bob Dylan (2009), Happy Holidays by Janet Devlin (2015), The Season's Upon Us by Dropkick Murphys (2012), Christmas Tree Farm by Taylor Swift (2019), Under the Mistletoe! by Elle King & Ronnie Spector (2019), Cozy Little Christmas by Katy Perry (2019), Glittery by Kacey Musgraves ft. Troye Sivan (2019), Love You More at Christmas Time by Kelly Rowland (2019), All I Want for Christmas Is You by Charly Bliss (2019), White Christmas by Janet Devlin (2016/2019), Toys, Toys, Toys by Laura Marano and Isabella Gomez (2019), Happy Xmas (War Is Over) by Lights (2019), I'm Gonna Spend My Christmas with a Dalek by The Go Go's (1964), Christmas in Killarney by The Irish Rovers (1999), Here This Christmas by Gwen Stefani (2020), My Kind of Present by Meghan Trainor (2020), Holidays by Josie Dunne (2020), It's Not Christmas Till Somebody Cries by Carly Rae Jepsen (2020), 12 Days of Christmas by Pentatonix (2020), Classic by Dallas Smith (2020), Lonely This Christmas, by The Academic (2020), Christmas Always Finds Me by Ingrid Andress (2020), Snow by Leslie Odom Jr. (2020), Christmas Calling (Jolly Jones) by Norah Jones (2021), Christmas Means Nothing Without You by Shonagh Murray (2018), More the Merrier by Sarah Reeves (2021), The Christmas Sweater by Michael Bublé (2021), Let It Snow by Broken Peach (2021), Drunk On Christmas by Darren Criss ft. Lainey Wilson (2021), Officially Christmas by Dan + Shay (2021), Merry Christmas, Happy New Year by Ingrid Michaelson feat. Zooey Deschanel (2021), Carol of the Bells by Journey Montana (2020), Kid on Christmas by Pentatonix ft. Meghan Trainor (2022), The Christmas Song by Claire & Dave Crosby with Mat & Savanna Shaw (2022), It's Beginning to Look a Lot Like Christmas by Broken Peach (2022), I Don't Know What Christmas Is (But Christmastime Is Here) by Old 97's (2022), Christmas Karaoke by American Authors (2022), Together This Christmas by Maisie Peters (2022), Meet Me Under the Mistletoe by Hailey Whitters (2022), Groovy Xmas by The Linda Lindas (2022).