Quirkiest Christmas Songs: Lady Gaga, William Shatner, and Other Unconventional Stars

Lady Gaga, William Shatner, Ludacris. Getty Images(3)

'Tis the season of Christmas, filling our senses with joy and cheer. Yet amidst the beloved classics like “Rockin’ Around the Christmas Tree,” there are holiday tunes that leave us scratching our heads. For every “All I Want for Christmas Is You,” there’s an unexpected gem like Lou Monte’s “Dominick the Donkey,” or a quirky miss like Elmo and Patsy’s “Grandma Got Run Over by a Reindeer.” Surprisingly, even A-list talents have delivered some of the most unusual and inexplicable songs of the season.

Lady Gaga featuring Space Cowboy, “Christmas Tree”

From a daytime talk show host doing a duet with a controversial businessman-turned-president, to a pair of Saturday Night Live alums gossiping about Santa’s “Banana,” and 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. Stick around for a list of the strangest entries in the holiday music canon.

The persona of Gaga in 2008 may appear unconventional to those familiar with her more refined image in A Star Is Born and Chromatica. Prior to her collaboration with the late Tony Bennett on two albums of traditional pop classics, she was fully immersed in her Fame Monster era for “Christmas Tree.” The song’s lyrics are a far departure from the depth found in “Shallow.” Instead, Gaga attempts to channel some holiday sexiness with varying degrees of success. “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 musical career has long been the subject of mockery and satire, but in 2004 he surprised many with the release of "Has Been", an indie album featuring spoken-word performances that won over a new generation of fans. In 2018, Shatner collaborated with Rollins on "Shatner Claus", a Christmas album that also showcased the talents of Iggy Pop, Brad Paisley, Rick Wakeman, Ian Anderson, Judy Collins, and Dani Bender. The duo's rendition of "Jingle Bells" was particularly bold and aggressive, and the album even included a bonus track featuring a "Punk Rock Version" of the classic holiday tune.

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 attempted to blend Christmas with Southern crunk, but certain lowbrow lyrics (“Just because I’m poor they always callin’ me a faker / And cause my Christmas tree is decorated in toilet paper”) prevented it from becoming a Christmas classic. Despite its lack of popularity, Ludacris is receiving rave reviews for his work in the 2023 film Dashing Through the Snow (and he recently discussed with We why he was so excited to film that holiday movie).

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Regis Philbin featuring Donald Trump, “Rudolph the Red-Nosed Reindeer”

Regis Philbin, an iconic television personality, passed away in 2020 after hosting Live alongside Kathie Lee Gifford and Kelly Ripa for over 20 years. What may come as a surprise is that Philbin also pursued a singing career in 1968 with his debut album, It’s Time for Regis. Despite its lack of success, Philbin continued to pursue his passion for music. In 2005, he released The Regis Philbin Christmas Album, featuring duets including “Rudolph the Red-Nosed Reindeer” with Donald Trump. Given recent events, such as Trump's indictment for attempting to overturn the 2020 election, this particular song might be reconsidered for future holiday playlists.

Ana Gasteyer featuring Maya Rudolph, “Secret Santa”

Gasteyer showcased her undeniable comedy skills, but in 2019, she also proved her singing and swinging abilities with the release of Sugar & Booze. The holiday album features a collection of big band, lounge, and bossa nova music with jazzy renditions of classics like “Let It Snow,” “Sleigh Ride,” and “You’re a Mean One, Mr. Grinch.” Throughout the album, Gasteyer exudes charm, although things take a slightly silly turn when fellow SNL alum Rudolph joins her on the wacky “Secret Santa.”

“Call me a banana, but I ventured down to Havana / To purchase a gift for my Secret Santa today / But I slipped on a banana, ended up in a cabana / Sipping rum and orange Fanta, so I guess I’ll just stay,” sings Gasteyer, using up almost every rhyme for “Santa” (including recycling “Banana” for a specific part of the Secret Santa) by the end of the song.

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 taking a fresh look at the infamous 1978 Star Wars Holiday Special, it may be a good time to revisit 1980’s Christmas in the Stars. The album showcased holiday songs with a Star Wars theme, such as “What Can You Get a Wookiee for Christmas (When He Already Owns a Comb),” “The Odds Against Christmas,” and the title track. One particular song, “R2-D2 We Wish You a Merry Christmas,” marked the first professional recording of John Bongiovi, a.k.a. Jon Bon Jovi. At the age of 17, Bon Jovi took the lead in the song, with backup vocals provided by a children’s choir. His cousin Tony Bongiovi co-produced the album, as revealed in a 2005 interview on TheForce.net.

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Calista Flockhart, “Santa Baby”

Ally McBeal was incredibly popular in its prime, so much so that a Christmas album was created in its honor. A Very Ally Christmas was predominantly a Vonda Shepard project, with featured covers by Jane Krakowski and a duet with Robert Downey Jr. The album also features Flockhart's full version of "Santa Baby," which she performed in one of the episodes.

Seth MacFarlane, “[Everybody’s Waitin’ for] The Man With the Bag”

MacFarlane's legacy is often associated with his creations like Family Guy, Ted, and The Orville, but his true passion lies in being a big band singer. In 2011, he debuted his first album, Music Is Better Than Words, which soared to the No. 2 spot on Billboard’s U.S. Jazz chart. His second album, Holiday for Swing, showcased his seasonal spirit as he crooned holiday favorites and lesser-known hits such as “[Everybody’s Waitin’ for] The Man with the Bag.” For fans of swing music, MacFarlane collaborated with Elizabeth Gillies to release their latest album, We Wish You the Merriest.

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Kylie Minogue and Iggy Pop, “Christmas Wrapping”

The original rendition of “Christmas Wrapping” is inextricably linked to The Waitresses singer Patty Donahue’s almost deadpan delivery of the song’s lyrics. As a result, Minogue’s interpretation of the 1981 track may be perceived as overly cheerful. However, the most peculiar aspect of the song is Pop, who makes sporadic appearances throughout the tune at the most unexpected moments. The song does indeed conclude with Pop enthusiastically proclaiming his skiing prowess (seriously!).

Christopher Lee, “The Little Drummer Boy”

The late Lee epitomized the classic movie villain, portraying Dracula in a series of films for the Hammer Horror production studio and embodying the cunning Saruman in the Lord of the Rings movies. What's less known is that Lee was also a powerhouse in the heavy metal genre. He created two symphonic metal concept albums inspired by the Roman emperor Charlemagne and two A Heavy Metal Christmas EPs. In the first EP, the actor who brought Count Dooku to life in the Star Wars franchise delivered a grand metal interpretation of “The Little Drummer Boy.” With Lee's deep voice and powerful drumming, it's a rendition that may not be everyone's cup of tea.