The Christmas season brings plenty of joy to our eyes, hearts and ears. But while the air is filled with classics like “Rockin’ Around the Christmas Tree,” some holiday tunes are less fa-la-la and more what the … ?
For every “All I Want for Christmas Is You,” there’s an oddity like Lou Monte’s “Dominick the Donkey” or an inescapable misfire like Elmo and Patsy’s corny “Grandma Got Run Over by a Reindeer.” Sometimes, though, the most unusual and inexplicable songs have come from A-list talents.
Be it a daytime talk show host doing a duet with a controversial businessman-turned-president, a pair of Saturday Night Live alums gossiping about Santa’s “Banana” or Jon Bon Jovi singing a special message to a droid in a galaxy far, far away, there are some truly bizarre Christmas songs out there. Keep reading for a list of the strangest entries in the holiday music canon.
Lady Gaga featuring Space Cowboy, “Christmas Tree”
The Gaga of 2008 might seem strange to those who know her as the more polished figure behind A Star Is Born and Chromatica. Long before she teamed up with the late Tony Bennett for two albums full of traditional pop classics, she was in her full Fame Monster era for “Christmas Tree.” The song’s lyrics are a far cry from any of the depth you might find on “Shallow.” Instead, Gaga tries to get sexy for Christmas with mixed results. “Here, here, here / The best time of the year,” she sings in a robotic monotone. “Take off my stockings we’re / Out spreading Christmas cheer.” While the holidays can be a fruitful season for romance, it won’t be found under this “Christmas Tree.”
William Shatner featuring Henry Rollins, “Jingle Bells”
Shatner’s music career has been a target of ridicule and parody for decades, but in 2004, he released Has Been, a spoken-word indie album that endeared him to younger generations. Shatner later teamed up with Rollins on 2018’s Shatner Claus, a Christmas album that also featured Iggy Pop, Brad Paisley, Rick Wakeman, Ian Anderson, Judy Collins and Dani Bender. Rollins and Shatner belted out a very aggressive version of “Jingle Bells” and included a “Punk Rock Version” as a bonus track.
Ludacris, “Ludacrismas”
Few hip-hop holiday songs have had the crossover appeal of Run-DMC’s “Christmas in Hollis,” but Ludacris tried his best with “Ludacrismas” from 2007’s Fred Claus. Luda tried to merge Christmas with Southern crunk, but some of the lowbrow lyrics (“Just because I’m poor they always callin’ me a faker / And cause my Christmas tree is decorated in toilet paper”) have prevented it from becoming a Christmas classic. While it didn’t take off, Ludacris is getting rave reviews for his work in 2023’s Dashing Through the Snow (and he recently spoke with Us Weekly about why he was so excited to film that holiday movie).
Regis Philbin featuring Donald Trump, “Rudolph the Red-Nosed Reindeer”
Philbin was a television icon when he died in 2020, having hosted Live alongside Kathie Lee Gifford and Kelly Ripa for over 20 years, but what might not be known is that Philbin was a crooner who attempted to launch a singing career in 1968 with his debut, It’s Time for Regis. Though the album was a flop, Philbin never let go of his music dreams. In 2005, he released The Regis Philbin Christmas Album, which featured several duets, including “Rudolph the Red-Nosed Reindeer” with Trump. A decade before being elected president, Trump appears as “The Trumpster” in the song, ready to hire Rudolph to “guide my sleigh tonight.” However, with Trump recently indicted for attempting to overturn the 2020 election, this song might be best left on the naughty list.
Ana Gasteyer featuring Maya Rudolph, “Secret Santa”
Gasteyer’s comedy chops are undeniable, but in 2019, she showed that she could sing — and swing — with the release of Sugar & Booze. The holiday collection of big band/lounge/bossa nova music is full of jazzy renditions of classics like “Let It Snow,” “Sleigh Ride” and “You’re a Mean One, Mr. Grinch.” Gasteyer is generally charming throughout, but things get a bit too silly when fellow SNL alum Rudolph joins her on the wacky “Secret Santa.”
“Call me a banana, but I went down to Havana / To buy my Secret Santa a present today / But I slipped on a banana, woke up in a cabana / Sippin’ rum and orange Fanta, so I think that I’ll stay,” sings Gasteyer, exhausting nearly every rhyme for “Santa” (including reusing “Banana” for a specific part of the Secret Santa) by the time the song is over.
Joe Pesci, “If It Doesn’t Snow on Christmas”
Pesci is forever associated with Christmas thanks to his role as Harry the burglar in Home Alone and Home Alone 2: Lost In New York, but he almost had a holiday hit on his hands with a song from his second album. In 1998, performing as his character from My Cousin Vinny, Pesci released Vincent LaGuardia Gambini Sings Just for You. In addition to originals like “Yo Cousin Vinny” and “Wise Guy,” the album includes the obscenity-laden holiday song “If It Doesn’t Snow on Christmas.” While hilarious, it’s definitely not for the kids.
Jon Bon Jovi, “R2-D2 We Wish You a Merry Christmas”
With 2023’s A Disturbance in the Force reexamining the disastrous 1978 Star Wars Holiday Special, it might be time to revisit 1980’s Christmas in the Stars. The album featured Star Wars–themed holiday songs, including “What Can You Get a Wookiee for Christmas (When He Already Owns a Comb),” “The Odds Against Christmas” and the title track. One song, “R2-D2 We Wish You a Merry Christmas,” is technically the first professional recording of John Bongiovi, a.k.a. Jon Bon Jovi. Then 17, Bon Jovi sung lead on the song with backup vocals provided by a children’s choir. His cousin Tony Bongiovi coproduced the album, according to a 2005 interview on TheForce.net.
Calista Flockhart, “Santa Baby”
Younger readers might not know just how popular Ally McBeal was during its heyday, but to clarify: The show wasn’t just big, it was “let’s make a Christmas album” big. A Very Ally Christmas is very much a Vonda Shepard project (the singer-songwriter appeared as a fictionalized version of herself throughout Ally McBeal’s run). However, the album sees Jane Krakowski cover “I Saw Mommy Kissing Santa Claus,” a pre–Iron Man Robert Downey Jr. duet with Shepard on “White Christmas” and Flockhart sing a full version of “Santa Baby” (which she did in season 3’s “Blue Christmas” episode).
Seth MacFarlane, “[Everybody’s Waitin’ for] The Man With the Bag”
MacFarlane will likely be remembered for creating Family Guy, Ted and The Orville, but he really wants you to think of him as a big band singer. In 2011, MacFarlane dropped his first album, Music Is Better Than Words, which reached No. 2 on Billboard’s U.S. Jazz chart. His second album saw him get into the seasonal mood with Holiday for Swing. MacFarlane croons some holiday favorites and lesser-known hits like “[Everybody’s Waitin’ for] The Man with the Bag.” If this kind of swing is your thing, MacFarlane teamed with Elizabeth Gillies to release We Wish You the Merriest this year.
Kylie Minogue and Iggy Pop, “Christmas Wrapping”
The original “Christmas Wrapping” is so tied to The Waitresses singer Patty Donahue’s near-deadpan delivery of the song’s lyrics. Thus, Minogue’s rendition of the 1981 track might be considered too cheerful. But the oddest thing about the song is Pop, who appears sporadically throughout the tune at the strangest intervals. We do get Pop ending the song by shouting about how well he can ski (really!).
Christopher Lee, “The Little Drummer Boy”
The late Lee was the quintessential movie villain, bringing Dracula to life in a series of films for the Hammer Horror production studio and playing the devious Saruman in the Lord of the Rings films. Lesser known, however, is the fact that Lee was also a heavy metal titan. He recorded two symphonic metal concept albums based on the Roman emperor Charlemagne and two A Heavy Metal Christmas EPs. On the first one, the man who played Count Dooku in the Star Wars franchise delivered an epic metal rendition of “The Little Drummer Boy.” Between Lee’s super-deep voice and drumming that could shake the manger, it’s a version that might not be for everyone.
