While I am not usually a fan of these kinds of lists, I do miss my annual tradition of sending holiday mix tapes, and later mix CDs, to friends and family. So a few caveats. Please note that this playlist does not suggest any particular hierarchy, but rather is sequenced in my suggested order of listening. It is also not intended to be definitive. I cede that authority to my friend and hero, Dr. Demento. (By the way, go to DrDemento.com for his holiday offerings if you want to get it from the master.) Lastly, this mix is definitely not safe for work. Or for trimming the tree with the little ones. Or for your church social. But if you’re up late one night, by yourself, wrapping presents, pounding the nog and you need a laugh or two, please enjoy this small stocking of my favorites. Oh… and I guess I’m now required by law to say this, so… Merry Christmas!

Tom Lehrer: “Christmas Carol”

It may be surprising to some that Tom Lehrer is, as of this writing, alive and well.  As his 90th birthday approaches in the New Year, the reclusive singer-songwriter has been basically out of the public eye for nearly a half century. But his legend and his body of work remain a cornerstone in the foundation of musical satire. Earlier this year, I spoke with Spinal Tap founding father Michael McKean, who offered this perspective on Lehrer’s legacy: “There were people who wrote really brilliant funny songs. Tom Lehrer being most of them.”

Brad Neely: “Prisoner Christmas”

When I began working for Turner Broadcasting’s new digital comedy platform Super Deluxe in 2006, one of our very first deals was with Brad Neely solely on the strength of his distinctive animated YouTube video, “George Washington.” Brad quickly became the most popular artist on Super Deluxe by far, leading to his two series on Adult Swim. But for me, nothing compares to the singular vision of his handmade Super Deluxe shorts, which feel like the love children of Gahan Wilson and Lin-Manuel Miranda.

Cheech and Chong: “Santa Claus and His Old Lady”

Cheech and Chong’s lavishly produced stoner comedy albums were improbably and yet wildly successful in the 1970s. This “B” side of their first hit single “Dave” released in December 1971 features the duo playing embryonic versions of their characters which would later be called “Pedro and the Man,” which, in turn, became the template for their eponymous motion picture alter egos years later. By today’s standards, their drug-addled counterculture routines seem almost adorably quaint and benign.  

Spinal Tap: “Christmas with the Devil”

When the improvised rockumentary spoof This Is Spinal Tap was first released, the fictitious band appeared as the musical guest on Saturday Night Live on May 5, 1984 to promote the movie.  According to my conversation with Harry Shearer (AKA Derek Smalls), he and bandmates Michael McKean and Christopher Guest decided to perform this song that wasn’t in the film because, “We thought it was a funny thing to do a Christmas song in May.” Over 30 years later, their cultural influence still resonates with the number 11 holding a numerological significance rivaling 666.

Allan Sherman: “The Twelve Gifts of Christmas”

Ironically, Jewish songwriters and recording artists have produced some of the perennially best-loved Christmas songs of all time. Irving Berlin. Barbra Streisand. Mel Torme. Neil Diamond. The list could go on to rival Schindler’s. (Sorry.) Not to be outdone, the great musical parodist Allan Sherman, whose Yiddish-inflected albums sold millions of copies in the 1960s, released his version of this holiday favorite, which went to #5 on the Billboard Christmas chart in 1963. And yet Sherman’s name has never appeared in any version of Adam Sandler’s “Hanukkah Song.” (It’s a shanda!)

Patton Oswalt: “Christmas Shoes”

While this playlist consists mostly of parodies of Christmas music or original comedic Christmas songs, this standup routine by generation-defining comedian Patton Oswalt savaging one of the most infamous terrible Christmas songs of all time is a shining holiday example of what Oswalt does best. It is the kind precise cultural dissection that is usually exemplified by Jerry Seinfeld or Jim Gaffigan, but in Oswalt’s case, he murders the subject and then performs the autopsy to show you why it needed to die. Just like that little boy’s mother. (Happy birthday Jesus!)

“Weird Al” Yankovic: “Christmas at Ground Zero”

While the aforementioned Dr. Demento almost single-handedly preserved the ongoing awareness of many of the older tracks on this list for years, he was entirely responsible for discovering the most successful, celebrated, and enduring musical comedy recording artist of all time. From his earliest accordion-arranged parodies “My Bologna” and “Another One Rides the Bus” almost 40 years ago, “Weird Al” has been a constant. A fixture. And this Christmas comedy classic is a testament to the fact that he is more than just a “pop culture Cuisinart,” as he has described himself. He is also a great writer of original silly songs. I’m just praying that North Korea and “Little Rocket Man” don’t decide to make this one come true this year.  

Sarah Silverman: “Give the Jew Girl Toys”

It may seem like an incongruous descriptor, but Sarah Silverman is a musical variety performer in a very classic sense. In many ways, she harkens back to the days of Vaudeville when comedians would sing, dance, act, and tell jokes. Silverman’s sense of the theatrical is a throwback, making the subversive substance of her work all the more startling. Her songwriting and vocal gifts are especially noteworthy and I have long believed that a Broadway musical written by and starring her could be the heir apparent to The Book of Mormon’s audience. Until then, I’ll just re-watch her genius musical opening number to her new Hulu series I Love You America. Oh and this…

Stan Freberg: “Green Chri$tma$”

As those of you who read my earlier Splitsider piece about Stan Freberg know, he is one of my great heroes. And one of my most cherished memories was having lunch with Stan when George Carlin stopped by our table to gush about how he almost got fired from his job as a disc jockey in Shreveport, Louisiana for playing “Green Chri$tma$” over and over, insisting to his boss that it was “the most moral record ever made.” It may surprise some to learn that Stan was the deeply religious son of a Baptist minister whose outrage regarding the commercialization of the holiday inspired this controversial contemporary reinvention of Dickens’ A Christmas Carol.   

Eric Idle: “Fuck Christmas”

As the musical Python who penned “Always Look on the Bright Side of Life”, Eric Idle remains capable, whenever the mood strikes him, of generating inspired, toe-tapping hilarity. So for those of you with a decidedly less rosy outlook on this most wonderful time of the year, I am closing out this set with Idle’s unambiguous screed that you will probably never hear at the mall or being sung by a children’s choir. It’s a delightful lump of coal for your ears.  

Dan Pasternack is a comedy producer and programmer as well as a scribbler and superfan who loves alliterative couplets almost as much as he loves comedy.

The Comedy Curator’s Christmas Cuts