Jimmy Fallon on His First Comedy Album in 12 Years

In the late-2000s, my dad got me hooked on Saturday Night Live. He wasn’t a weekly watcher, still largely hung up on the “glory days” of 15 years prior, when Adam Sandler and Chris Farley and Dana Carvey ruled Studio 8H. But, after noticing how thrilled I was by the time capsule of comedy magic that the show so deeply was, he and my mom started gifting me with “Best Of” DVDs. The discs would focus on specific cast members, acting as greatest hits collections of their best material. It started with Farley, and then it was Will Ferrell. And then it was Jimmy Fallon, who I’d loved in Fever Pitch and felt captured the very essence of the SNL I fell in love—his constant breaking with Horatio Sanz, his ability to spoof James Taylor and Eddie Vedder in a matter of seconds, his boy-next-door likability on Weekend Update. His all-time recurring skit with Justin Timberlake, “The Barry Gibb Talk Show,” is still my dad’s favorite SNL bit, one he rewatches religiously.

But few SNL moments linger in my memory with as much joy as the “I Wish It Was Christmas Today” performance does. Fallon, Sanz, Chris Kattan and Tracy Morgan stood (and danced) on stage, as Sanz plucked a mini guitar and Fallon played a ditty on the keys. “I don’t care about anything except hearing those sleigh bells a’ring-a-ding, ding.” It was poetry in motion, such a perfectly executed holiday song with a bare-bones concept and two instruments.

And, in what feels like another lifetime ago, I found myself staying up late so I could binge as many Late Night with Jimmy Fallon sketches as possible: “Water War,” “Slow Jam the News,” “Ew,” “Joking Bad.” But it was “Neil Young Singing ‘The Fresh Prince of Bel-Air,'” or “First Drafts of Rock,” or Fallon and Florence Welch singing “Balls in Your Mouth” that really hooked me in, dropping the same kind of bliss onto my taste buds that Fallon impersonating Third Eye Blind on Update had years and years before. I was there on the frontlines when Blow Your Pants Off, Fallon’s breakthrough, post-SNL comedy album came out. He put “The Doors Singing ‘Reading Rainbow’” on there, “Bob Dylan Sings ‘Charles in Charge’” too. It went Platinum in my house.

This is all just to say that now, 12 years later, Fallon has returned with his next album of new material. Holiday Seasoning it’s called, 16 songs featuring some of the biggest names in pop: the Jonas Brothers, Meghan Trainor, Ariana Grande and Megan Thee Stallion, Dolly Parton. Some non-music names appear as well, like Ferrell, Chelsea Handler and Cara Delevingne. Fallon foregoes the obvious holiday song tropes, writing about coquito instead of eggnog and balancing big, infectious jams like “Hey Rudy” and “Holiday” with quiet, singer-songwriter textures on “How You Know It’s Christmastime” and “Hallmark Movie.” He’s conjuring Dylan as much as he is disco, pairing bombast with piano interstices. He’s covering Thanksgiving, New Year’s Eve, Christmas and all the days in-between. It feels like a proper end-cap to this part of Fallon’s career, as he continues his 20-plus-year collaborations with Ferrell and Timberlake.

Last week, I caught up with Fallon about Holiday Seasoning, assembling a coterie of A-listers, working with “Weird Al” Yankovic, and recording “Silent Night” during a blizzard. This interview has been edited for clarity.

Paste Magazine: How are you doing?

Jimmy Fallon: I’m so excited about this. I’m proud, it’s a good one. This is a fun project to have. I can’t believe I have my own Christmas album. It kind of makes no sense, but here we are!

A couple of these songs, like “Masked Christmas,” “Almost Too Early For Christmas” and “Wrap Me Up,” have come out periodically over the last few years. You mentioned on your show a few nights ago that it took 25 years to make this, but at what point did you figure out that you wanted to make a full record of holiday songs?

What really happened, the true story, is Michelle Anthony, who’s the head of Universal, I was talking to her and she said, “You should do an album like 12 Days of Christmas Sweaters and you just do 12 covers and make it sound good with the big band, or something.” And I go, “Okay, that sounds amazing.” And I recorded one and it wasn’t good. It was corny. I don’t know what it was. It wasn’t me. It was like, “I’m not good at this. Michael Bublé is much better at doing this. Kelly Clarkson, Mariah Carey—the real singers. This is not what I can offer.” So I go, ‘I have a comedy song that I was working on on my iPhone.’

I had a song called “Chipmunks and Chestnuts,” which is a “Roy Orbison-inspired, Slim Whitman, Monty Python-type of song,” I would say, where a guy hits a giant high note that’s almost annoying. It makes me laugh. So, I recorded that, and then I started adding tracks to that. Then I go, “Maybe I won’t do any covers, I’ll just do all original songs.” I thought that was more of a challenge. If you can write a comedy holiday album—I don’t know when the last one was, but we’re overdue for one, so might as well just do it now and have fun. You get this opportunity to create new stuff and just put it out there and see what sticks, you know? That was kind of my idea, or my intention—to just start making things. You go, “Oh, I have an idea for a punk rock song, or I have an idea for a Paul McCartney-esque type of song” and start recording stuff.

We were recording at Electric Lady, and it was a blizzard—it was one of the two blizzards New York City had [in 2023]. We don’t really get snow anymore, but my wife was like, “You’re going to the studio, right?” And I go, “Yeah… or not? I could just come home! It’s a blizzard.” She’s like, “No you should go to the studio.” She was very positive, driving me towards working. This is after The Tonight Show, so I took my time. I went to Electric Lady and no one was there. It was empty. The streets were empty! So, it was just me and an engineer and no one to play instruments—no one to bounce in, no one to write anything with. So, I was just like, “Let’s try to make this something.” I did a version of “Silent Night” with just me on the guitar and harmonizing with myself, using the mic case as a drum. I did that and I did “Little Drummer Boy,” the only two covers that are on this album.

The canon for holiday songs is massive at this point.

And you just have to have a different take on it. The big band stuff wasn’t my thing. I didn’t do any of that stuff. There’s a Bob Dylan-influenced one, there’s a couple college radio type of keyboarding jams where I go, “Yeah, I don’t know if anyone’s gonna get this one, but I think it’s funny. The couple pop jams on there that, hopefully, can get radio play—I like those, it’s like a roller disco-type of song called “Holiday” that I think everyone can get behind. I actually have the first version that I wrote. It was originally called “Silent Night Again”—doesn’t sound like a fun song, but this wasn’t a cover. [Jimmy plays an early draft of “Holiday” on his phone.] That turned into “It’s a holiday, time to celebrate, we’ll stay out all night” and then you add bass and you make it more Jacksons, more Chic. Then it turns into that, and I go, “Would the Jonas Brothers do this?” We sent it over to their people and they were like, “Love it. Let’s do it. Let’s play.” They recorded their version of it and they turned it into a real song.

You’ve been writing musical material, be it songs or skits, for a few decades now. “I Wish It Was Christmas Today” is almost 25 years old. What is that fascinates you about pairing Christmas with music especially, how did it become the right vehicle for your musicality?

It’s interesting. We have Julian Casablancas coming on the show tonight, who did a cover version of “I Wish It Was Christmas Today.” I think it’s that “holiday seasoning”—that time where you just hear the same kind of music all over the city, or wherever you are. It’s on the radio, it’s everywhere, and it brings people together. It gets you in a good mood. So, people are open to hearing music—everyone can relate to music. I think it’s a global thing, especially around the holidays, no matter what your religion is. People are listening to music and getting together and having parties. I think music is a good ingredient to a good party.

Back in the SNL days, I would try to write a holiday song. Horatio Sanz wrote “I Wish It Were Christmas Today,” because, for Christmas, someone got me a tiny guitar—a backpacker guitar, which I guess you were supposed to wear while hiking. I don’t know what you do with this little guitar, but we had it in the office and he kept playing with it. It had a little dinky sound to it, and then he was playing with it and he came up with this riff. I had this old keyboard, which I always have still around the office, just from the ‘80s that has pre-recorded, different chords and drum beats on it. [Jimmy picks the keyboard up from the floor next to his desk.] I started grooving with him and acting like we’re musicians making a really good song. And it was just so lo-fi that it’s an earworm. It sticks in your head.

There are big names on here, like Ariana Grande and Megan Thee Stallion, Meghan Trainor, the Jonas Brothers. But there are a handful of moments where it’s just you performing solo. Talk to me about the difference in dynamic. Is it easier to go in alone, or does having another singer alongside you and having that collaborative energy make a difference you can’t quite hear on the finished product but exists in the margins of how it was made?

I think I have a little bit more confidence when I’m doing it by myself, just because I can take risks and be weird. I don’t know if I would want to put another artist through that, of being too odd. Ariana has a great sense of humor, so she’s down for that. [Justin] Timberlake will do that. With this [album], it’s a first. Maybe if this works, I can do another one. I just don’t want to let anyone down. I’ll talk to my therapist about that, but I just want to, when I’m with an artist, make sure it’s all written, ready to go, set, professional and I’ll try to hit my notes. Getting Dolly Parton to do a song on the album was crazy to me. It’s something I never thought would ever happen in my life. I remember her leaving a message for me and playing it for my dad and my sister. We were like, “This is the real Dolly Parton!” She’s amazing. I feel like, if I did another song with Dolly, I can get a little more weird and go, “This one’s odder than the other one.”

You learn from watching these artists. Timberlake is insane. I’ve never seen anyone like Justin Timberlake. I know I’m friends with him, but you ever go to your friends’ work and see what your friends really do for a living? It’s odd, because you’re like, “I know you, but you don’t really—” You go watch them work, I’m like, “Oh, my gosh. He produced the whole thing. He harmonizes with himself, he plays instruments.” It’s insane. And then, on top of that, we’re laughing and re-writing lyrics. We have that bromance song [“You’ll Be There”] that’s about me calling him and I want to hang out with him during the holidays and he won’t call me back. That gets funny. We wrote that one with Ryan Tedder. You go to these studios and other people are in the room next door. You go, “Oh, do they want to play? Does Ryan want to do anything?” Ido [Zmishlany] was our producer, but Greg [Hein] was around, who wrote “Flowers” with Miley Cyrus. I was like, “Do you want to come and hang out? We’ll write a song.” And they go, “Yeah!” It was weird. It was almost like a weird camp experience.

Holiday Seasoning marks your first full-length comedy record in 12 years. What’d you learn from making Blow Your Pants Off that now, all these years later, made you feel like you were in a place where the work you were going to do on whatever the next project was going to end up becoming would be some of your best?

Don’t overthink it. Release it, put it out. I have artists come on the show sometimes and they go, “Yeah, we cut this down. I wrote 103 songs, we cut it down to 10. I go, “You wrote 103 songs? Oh, my gosh. If I ever wrote 103 songs, my album would have 103 songs on it.” Are you kidding me? I would be so proud. So, don’t overthink it. Don’t go “Someone’s gonna make fun of me for this one.” Put it out! It’s something else to listen to. You go, “This one’s weird, but I kind of like it” and it could inspire some other kid out there that goes, “Hey! I want to write a comedy song.” You never know. “Christmas Ding Dong” could inspire the next national anthem, I have no idea.

You do a song with “Weird Al,” who was able to make music comedy without turning it into a novelty in ways no else had then or has since. Those songs of his, like “Eat It” or “My Bologna,” they aren’t just spoofs—they’re such well-done compositions. As an apostle of his work, how has his approach to the craft influenced yours, and how full-circle was it for you getting to have him on the album?

He’s my idol. I grew up—there was a DJ called Dr. Demento that I used to listen to on Sunday nights, Westwood One Radio. He would play novelty songs on Sunday nights. I’d listen to it, and you’d just hear the weirdest music. I mean, he would have the “funny five,” at the end of the countdown, of all these old, weird novelty songs—new ones and old ones. But “Weird Al” was emerging at the time. This is around the “Eat It” years. I remember really getting into and going, “Oh, I’d like to write parodies.” He got famous for his paraodies first, and then, when you buy the album, you get into the deeper cuts and “Dare to Be Stupid” and his polka stuff. I was writing all these songs for the album, and I was trying to hit every holiday that I could think of. I was thinking about New Year’s Eve, and there’s no real happy New Year’s Eve songs. They’re all sad, they’re all depressing. That’s covered. There’s no missing sad New Year’s songs. We have a lot of them, whether it’s “Auld Lang Syne” or Dan Fogelberg, or whatever.

But I was like, “What’s the one genre that you just have to smile at?” That’s polka. On my iPhone, I was just [singing] “Ten, nine, eight, seven, six, five, four, three, two, one, hey!” but better. And I was thinking about these parties I used to have at my parents. At my house, in our dining room, was me and two of my friends. We were called the Born Losers and we would just play cover songs for an hour and just have a full-on rager New Year’s Eve party. I wanted a good song that you just put on at a New Year’s Eve party and have everyone go, “This is so silly that I have to dance around.” I’m picturing mosh pits, I’m picturing people screaming at the top of their lungs. I purposefully put it as track one on side two of the album, just because, if someone had a couple cocktails, they don’t have to think about “What groove am I looking for on this record?” You don’t get the flashlight out. It’s track number one, side two. Me, “Weird Al” Yankovic and the Roots.

I sent it to him. I said, “What do you think of this?” He immediately got back, goes “I’m in. I love it. Do you mind if I rewrite a couple things?” I said, “Yeah, let’s go!” We started going back and forth. In two days, he had a full-on recorded version of it—full sheet music of every note and every harmony. Advanced stuff. I recorded [the demo] blowing on recorders, just to hit [the notes], because it sounds like an accordion to me. That’s the closest thing I could do for playing the accordion for a scratch track. Then, he took it to the next level. And he goes, “Are you gonna get a band on this?” I go, “I can…” I didn’t think about that. I go to Questlove. I go, “I have a song with ‘Weird Al’—” He’s like, “I’m in,” before I finish the sentence. [“Weird Al”] is a legend. He’s the one and only. I’m so honored to work with him. He was my idol. I wanted to be “Weird Al” Yankovic.

So many of us did.

Jimmy Fallon’s new album, Holiday Seasoning, is out now.

Matt Mitchell is Paste’s music editor, reporting from their home in Northeast Ohio.