Jimmy Fallon On Being The “Nerdy Dad” At Halloween

Becoming the “King of Late Night,” an NBC mascot just as much as the colorful peacock itself? That kind of fame was on the trajectory for Jimmy Fallon. He may not have intended it when he started working for Saturday Night Live in 1998, but it’s a path that makes sense. Writing children’s books and becoming a New York Times best-selling author? That really wasn’t in the cards.

Like, at all.

“It’s like the weirdest thing for me because it’s clearly not my thing,” Fallon tells me over the phone. “I’m not an author.” It’s a funny thing to say when you’ve written five children’s books since 2012, each of them debuting at #1 on The New York Times Bestseller List, but Fallon really means it. Writing children’s books was never the plan, but now that he’s done it a few times, he finds inspiration in a lot of places. His new book, 5 More Sleeps ‘til Halloween, releases Sep. 3, 2024, and is bound to be another fan favorite. Inspired by the success of 5 More Sleeps ‘til Christmas, Fallon wanted to find another exciting moment that a kid would readily countdown towards.

“I never heard the term [how many sleeps] and my daughter said it to me once,” Fallon says. “She’s like, ‘How many more sleeps ‘til we go to Noma’s house?’ And I’m like, ‘How many more sleeps? That is so cute.’ So I did 5 More Sleeps ‘til Christmas and it came out and it worked and people liked it. I’m like, there’s got to be another five more sleeps, just getting excited for something. I didn’t know what it was going to be, maybe a first day of school or a birthday? But then I’m like, ‘Halloween could be fun.’”

And he’s right — Halloween is so fun, in so many ways. And it comes across so beautifully in the book. (Fallon also says that while looking for Halloween books for his own kids to read, he struggled to find a favorite for his kids’ age group and figured why not fill that hole?) While so many of the holidays have become overwhelming — a constant drumbeat of more, more, more — Halloween has stayed pretty much the same as it always was. In 5 More Sleeps ‘til Halloween, one little guy focuses on all the upcoming fun of the holiday by counting down from five days out as he does things like prepping his costume and getting BOO’d by a neighbor. I especially love that it’s not a countdown of epic activities, something his mom would have to Pinterest the hell out of to make happen — it’s just the same kind of sweet excitement and fun you’ve always had as a kid during the spooky season.

I tell Fallon that I think of Halloween as the great equalizer. When people get nostalgic about good old-fashioned Halloweens, I feel like, for the most part, the celebrations still look the same. Except for the costumes.

“My sister and I always had the worst costumes,” Fallon tells me. “We were always old people every year.” Growing up in a middle-class family, Fallon says Halloween was all about DIY — except for the time they got to pick out “those cheap plastic costumes” that were a mainstay of the ‘70s and ‘80s.

“Do you remember those? In a box?” He asks me. “They always had a plastic face, and I think I had a Batman one with a plastic Batman face, and it ripped and it cut my lip after a while. The outfit itself was made out of basically a kind of plastic garbage bag. And remember, I was Batman, so I jumped off the first stoop of the neighbor’s house trick-or-treating, and it ripped completely. It was just so cheap; the whole thing was like a cape after that. It was just a disaster. I was like, well, I guess I’ll go back to being dressed like an old person.”

In 5 More Sleeps ‘til Halloween, the costume chatter feels so real. One of the characters decides to change her costume entirely — two days before Halloween — and the other is still struggling to make a decision. Fallon tells me about his daughter Winnie being a bowl of ramen for Halloween the year she was 2, and I share with him how my own daughter wanted to be an inflatable chicken last year — and then the motor broke halfway through trick-or-treating. (“So you just carried a deflated chicken down the road?” he asks me.)

When I tell him about that same daughter’s first Halloween, where I made her a cat costume and everyone called her a penguin all night, he laughs and tells me about his own wife’s DIY costumes. “One year, oh my gosh, my daughter wanted to be a butterfly, and my wife spent three months making this butterfly costume. And she was like, ‘Here it is. Do you like it?’ And she was like, ‘Mom, I don’t want to be a butterfly,’” Fallon says. “And my wife was like, ‘You have to be. I worked on this, so you have to be. I don’t know what to tell you.’ And my daughter goes, ‘I want to be a dragonfly.’ My wife said, ‘OK, I’m going to add a tail to the butterfly.’ Boom. That’s it. Now it’s a dragonfly costume.”

That sweet realism is throughout Fallon’s book, and while he may not call himself an author, being a writer who has memories from childhood or takes certain moments from present-day life and puts them into scenes in a story is extremely author-coded. In 5 More Sleeps ‘til Halloween, the characters get to celebrate with a parade — “It was a thing at school, [people would get dressed up,” he tells me — and get to experience the trend of being “BOOd” by a neighbor — something that happened to Fallon recently and he loved. And it’s one of the ways the holiday, while still pretty simple, has grown and gotten bigger.

“That’s a new thing I didn’t have growing up,” he tells me. “Like a Secret Santa.” We both laugh about the awkwardness of knocking on someone’s door, and Fallon says about two years ago, it happened at his home for the first time. “I didn’t know what it was, and there was a knock at the door. I’m like, huh? I opened the door and there were kids outside laughing, and it was very nice. There was just a bag of candy. I grabbed my daughter to look, and then I felt like the nerdy dad. I’m like, ‘Oh cool, look, we got BOOd, guys!’ like I knew what it was. I’m like, oh my God, I’m clearly so lame. If there are kids outside knocking, I’m just going to let my daughter answer the door from now on.”

But that experience made its way into the book, as did all of the other little sweet moments and realizations about Halloween. Fallon shares how much he loves the holiday, how experiencing it with his own kids has been so special. “Everyone’s in on it, all the costumes and trick-or-treating. We teach our kids not to talk to strangers, then one day a year you’re like, ‘Walk up to that stranger’s house and take food from them.’ It’s a tradition. It’s like their first, I don’t know, not dance, but a social event. They’re going out with kids their size and their age and they’re experiencing a good social thing together. I’m like, oh yeah, Halloween, it’s here to stay.”

And Fallon’s going to help you get excited about it.