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"The Chanukah Song"

By Adam Sandler

(“What the Hell Happened to Me?” 1995)

Many of the best known Christmas songs were penned by Jewish songwriters. But it wasn’t until Sandler debuted this silly number (about Jews being left out of the holiday season) on “Saturday Night Live” in December 1994 that a Hanukkah song entered the holiday canon. In fact, this ditty is so enduring that Sandler has updated it three times. Sandler still performs it in his comedy act. This summer, the crowd at Treasure Island Casino in Red Wing roared when Sandler encored with this tongue-in-cheek tune that always brings tidings of levity and joy.

Jon Bream, music critic

“Christmas Time Is Here” (Instrumental)

By the Vince Guaraldi Trio

(“A Charlie Brown Christmas,” 1965)

A dry martini toast to Yuletide from a quintessentially cool pianist. Guaraldi has always been one of my jazz heroes for adding introspective adult themes to the “Peanuts” animated TV specials, always the best parts of the shows. The elegance to his downbeat composition and slow, loping playing don’t require the children’s church choir of the song’s vocal version. This is a crisp cocktail homage to the season that I want straight, no chaser.

Colin Covert, film critic

"Silent Night"

By Al Green

("The Christmas Album," 1983)

Tree lights twinkling, kids tucked in bed, eggnog with a splash of rum — that’s my ideal scenario for playing Christmas music. “Silent Night” is a lifelong favorite. I grew up listening to Frank Sinatra’s version, smooth, controlled and pitch-perfect. So when I first heard the Reverend’s, I couldn’t quite believe my ears. Yes, it starts with a calm hush, but builds with improvisation and runs to a soulful crescendo, giving the classic carol an injection of … sexy. Add another splash of rum and a shimmy to the singalong.

Sue Campbell, assistant managing editor, features

"Have Yourself a Merry Little Christmas"

By Cécile McLorin Salvant

(Jazz at Lincoln Center Orchestra's “Big Band Holidays," 2015)

Like the bitters in an Old ­Fashioned, a dash of heartache makes holiday tunes ring true. With lines such as “We all will be together if the fates allow,” the song is anything but merry. That queen of pain Judy Garland first tugged hearts with it in the 1944 film “Meet Me in St. Louis.” Rising vocal star Salvant made it her own 60 years later at Orchestra Hall, in concert with Wynton Marsalis' big band. With a caressing, almost girlish tone, she treats the plaintive melody as a gift wrapped in sentiment that’s pretty but tissue-thin.

Tim Campbell, senior arts editor

“The First Noel”

By Wild & Blue

(“Blue Ridge Mountain Christmas,” 2012)

A few Decembers ago I was driving around town with my daughter, running a few last-minute holiday errands. It was late Saturday morning when we pulled up to Calhoun Square and I hesitated before pulling out the car key. The bluegrass song on the radio was beautiful, with its sisterly harmonizing and vibrato strings. I wanted to hear more. I let the vehicle idle as I turned to my preschooler in the back — and found her eyes welled with tears. I reached for her tiny hand. She laughed a little, embarrassed. And then we listened to the rest of this gorgeous hymn.

Christy DeSmith, assistant arts editor

“Ugly Christmas Sweater"

By Jeremy Turner

("Ugly Christmas Sweater," 2012)

I don’t celebrate Christmas but do enjoy the spectacle and kitsch of the holidays. I love an ugly Christmas sweater, especially one purchased and worn for the season. This song is terrible and jazzy, and just as cheesy as an actual holiday sweater. As a Jew, I’ve tried to make the Hanukkah sweater work, but there's just not the same level of gaudy consumerism. All hail the hideous Christmas sweater! Not to mention all those grotesquely gorgeous lights and lawn ornaments.

Alicia Eler, art critic

“Joy”

By Tracey Thorn

(“Tinsel and Lights,” 2012)

Sorry, “A Charlie Brown Christmas,” but I’m going with this wistful song from the Everything but the Girl singer’s Christmas-adjacent solo album of a few years back. Inspired by the serious illness of her partner in life and (sometimes) music, Ben Watt, “Joy” is about how the holidays help us remember the joys of the preceding year: “You loved it as a kid/And now you need it more than you ever did/It’s because of the dark/We see the beauty in the spark.”

Chris Hewitt, theater critic

"Christmas in Hollis"

By Run DMC

(“A Very Special Christmas,” 1987)

Without a doubt, this jam is guaranteed to transform any Christmas playlist into a full-on party. In 1987, hip-hop was still pretty new on American airwaves and on MTV. Maybe that allowed for a mega rap group like Run DMC to experiment and actually release a Christmas song. Could you imagine Drake or Kanye West doing that today? The accompanying music video solidified the song’s place in the pantheon of pop Christmas songs. Rolling Stone magazine even awarded it video of the year over Michael Jackson’s “Bad.”

Tom Horgen, digital features editor

"River"

By Joni Mitchell

("Blue," 1971)

Enough with the jingle-bell rock. The song that best wraps up the coldest and loneliest of seasons is this mournful ballad about a spurned lover whose holiday wish list includes a river she can skate away on. Holiday purists may consider this tear-jerker to be nothing more than a lump of coal, but those of us who trudge through the season in snow boots can take solace in knowing there's a song out there to accompany our humbug disposition.

Neal Justin, TV critic

"Holly Jolly Christmas"

By Burl Ives

("Have a Holly Jolly Christmas," 1965)

Spotify is missing “The Great Songs of Christmas” album put out by Goodyear Tires in 1965 — the greatest holiday LP ever recorded — so I’ll go with another childhood favorite, “Holly Jolly Christmas.” Burl Ives recorded the song for the beloved “Rudolph the Red-Nosed Reindeer" special, but the version you know is from his “Have a Holly Jolly Christmas” LP. Arranged by Nashville studio legend Owen Bradley, it’s a perfect little song — and you can hear Santa’s chuckle in Ives’ voice.

James Lileks, columnist

"Santa Baby"

By Eartha Kitt

("Santa Baby," 1953)

The ghosts of Nat King Cole and Ray Charles will no doubt be vexed by this, but Eartha Kitt’s wit and allure won me a long time ago and she's hard to shake. Truly. She injected such drama and flair into this song, not to mention irony, that she wins on pure theatricality. Of course, there have been others who’ve covered “Santa Baby,” including Ashanti, Gwen Stefani and Kylie Minogue. All decent efforts that only point to the mastery of Kitt’s original.

Rohan Preston, theater critic

“Christmas Kisses”

By Ray Anthony and His Bookends

(“Ultra-Lounge: Christmas Cocktails, Part One,” 1996)

This earworm of a song has been imprinted on my yuletide consciousness ever since I first encountered it 20 years ago in “Nutcracker (not so) Suite” at Ballet of the Dolls. Choreographer Myron Johnson always used its kitschy bubbliness to maximum effect. It also helps that the playfully vapid lyrics (“Santa can keep the hi-fi set, there’s something that is better yet”) and bubbly girl-group melody are such silly “Mad Men”-era departures.

Rick Nelson, restaurant critic

"It Came Upon a Midnight Clear"

By Jackie Evancho

("Someday at Christmas," 2016)

Nobody reflects the tinsel glimmer and porcelain polish of the holiday season like the angelic Miss Jackie, who got her big break at age 10 on the gift-that-keeps-giving TV show “America’s Got Talent” and has become a PBS music icon by age 17. You can almost feel the guiding presence of the star of Bethlehem beckoning over her shoulder as her majestic voice takes flight with still beauty.

Chris Riemenschneider, music critic

"Snow Days"

By the New Standards

("Candy Cane," 2011)

Nobody craves Christmas music more than this Jewish girl. And nobody tries harder not to drive off the road lost in holiday euphoria while listening to the New Standards’ showstopping “Snow Days.” Featuring John Munson on vocals, Chan Poling on piano and Steve Roehm on the band’s signature vibraphone, with joyful assist from brass, strings and backup vocals, this exhilarating tune makes me want to do only one thing: Go home and take a snow day!

Gail Rosenblum, columnist

"Just like Christmas"

By Low

(“Christmas” 1999)

On first listen, “Just Like Christmas” is a catchy, Christmas-y pop tune full of snow and sleigh bells. It’s definitely the cheeriest track off the Duluth trio’s “Christmas,” an eight-song EP that is otherwise spare, gorgeous and sometimes strange. But this song’s few, sweet lyrics are nostalgic, too, and a little sad. Which is just how I like my Christmas music. “By the time we got to Oslo, the snow was gone,” Mimi Parker sings, her straightforward tone set above a fuzzy vintage organ. “And we got lost. The beds were small. But we felt so young.”

Jenna Ross, arts and culture reporter