2009 marked a crucial turning point in Jimmy Fallon’s career. After his departure from Saturday Night Live in 2004, he spent a few years pursuing a movie career; although he’d landed starring roles in Taxi and Fever Pitch, both films fared poorly with audiences and critics alike. The future Tonight Show host would later refer to this time in his life as a “kind of lost period,” admitting that he was unsure about what to do next.
All that changed in March 2009, when Fallon succeeded Conan O’Brien as host of NBC’s Late Night. At the time, the idea that Fallon—who was then just 34 years old and still reeling from a string of box office flops—could be the new face of such an institution was met with more than a few raised eyebrows. According to Fallon himself, NBC was skeptical of his abilities until Lorne Michaels personally went to bat for him. And just like that, a new chapter in late-night history was born.
As Late Night with Jimmy Fallon was just starting to take off, Gossip Girl was at the height of its powers. The teen drama series, which was co-created by Josh Schwartz and Stephanie Savage and loosely based on the book series of the same name, originally aired on the youth-skewing CW network from 2007 to 2012. The show’s influence was vast, and it remains a pop culture staple to this day. In fact, the show, which is currently available on three streaming platforms (Hulu, Max, and Netflix), was the 10th most-watched show on Nielsen’s most recent streaming chart.
With Gossip Girl set in the heart of New York City, it only made sense that one of the characters would eventually cross paths with the world of late-night TV in some way. Sure enough, in the fall of 2009, the ultimate millennial television crossover happened: Gossip Girl, Hilary Duff, and Jimmy Fallon.
At the time, Duff was guest starring on Gossip Girl as Dan’s [Penn Badgley] new celebrity girlfriend, Olivia. The Season 3 episode “The Grandfather Part II” sees Olivia guest on Late Night with Jimmy Fallon, where she accidentally reveals an embarrassing secret that stands to jeopardize the couple’s relationship. Fallon himself cameos in the episode, and plays a key role in the storyline.
In honor of the episode’s 15-year anniversary, LateNighter spoke with Gossip Girl co-creator, showrunner, and executive producer Stephanie Savage; “The Grandfather: Part II” director Mark Piznarski; and Gossip Girl story editor and “The Grandfather: Part II” writer Lenn K. Rosenfeld about Fallon’s memorable guest stint.
STEPHANIE SAVAGE (CO-CREATOR, SHOWRUNNER, EXECUTIVE PRODUCER): At the time, Fallon had just taken over [Late Night]. It was exciting to have a younger person at the helm of that show. It felt really fresh and fun that Jimmy was taking on this new job—it was exciting for television and culture that this shift was happening.
My first job in Hollywood was working at Drew Barrymore and Nancy Juvonen’s company, Flower Films. Nancy’s brother, Jim, was a beloved friend of mine who was working on Fallon’s show at the time. Nancy and Jimmy were already married by then. So I knew somebody at [Late Night] that I could easily reach out to and be like, “Would you guys think this was fun, to have Jimmy Fallon on Gossip Girl?” [Jim Juvonen] pitched it, and everybody really liked the idea.
LENN K. ROSENFELD (STORY EDITOR, EPISODE WRITER): I actually went and rewatched the episode last night, because I hadn’t seen it in forever. We started breaking it in the summer of 2009. It was the third season of the show.
SAVAGE: Season 3 was a real high point. That was the year Blake [Lively] did Saturday Night Live. That was the year Blake and Leighton [Meester] were on the cover of Rolling Stone. It was a real cultural moment for the show.
A long list of Gossip Girl cast members guested on Late Night in 2009: Chace Crawford (Nate) on March 6; Leighton Meester (Blair) on April 2, Ed Westwick (Chuck) on September 9; Penn Badgley on October 12; and Blake Lively (Serena) on November 23.
MARK PIZNARSKI (EPISODE DIRECTOR): We had pretty good luck in getting real people to be on the show. It was just a phenomenon, you know? It was part of the zeitgeist. People refer to something as a Gossip Girl thing, and everybody knows what that means. I think it might even be in a dictionary.
SAVAGE: Having a fictional character appear on a real talk show was a pretty exciting moment. It kind of captures the moment of [Gossip Girl’s] success at the time, that we were able to do something like that, that there was interest and support. It was something exciting for everybody.
In “The Grandfather Part II,” a jittery Olivia inadvertently tells Fallon (and the world) an embarrassing story about Dan. On air, she reveals that on the couple’s first date, Dan came back from the restroom with his shirt on inside out because a spider had apparently crawled up his shirt. Fallon finds the story hilarious and nicknames Dan “bathroom boy,” and the interview clip subsequently goes viral.
The “bathroom boy” story was actually based on something that happened to Rosenfeld in real life: a spider crawled up his shirt on a first date—for real. Although it was many years ago at this point, he can still recount the entire horrifying incident like it happened yesterday.
ROSENFELD: As [my date’s] talking to me, I literally am not hearing a word she’s saying, because all I could think about is this damn spider is somewhere inside my clothes right now. It literally was like a Charlie Brown episode where you hear voices and you’re not hearing what they’re saying. I felt terrible, but I couldn’t stop thinking about the stupid spider. … So I excused myself to the bathroom, stripped down, shook my clothes out, and then returned to the table a whole new person.
I don’t think we necessarily were thinking, “Oh, we’re going to use this in Gossip Girl.” It was more just me on a Monday morning telling people how my weekend went. … Half the things we say in the writers’ room, we don’t end up using them. [But] sometimes someone will be like, “Oh, that reminds me of the time…” and then, next thing you know, you’ve got a great episode of television.
SAVAGE: The idea was that Olivia would sort of accidentally tell an embarrassing story about Dan that then Jimmy would latch onto and amplify. Of course, it was on television, so it was extra amplified. And then that would cause problems in their relationship that they’d have to deal with the fallout.
ROSENFELD: We obviously added the twist, which was that Dan said the spider thing, and really, he was sweating.
The Gossip Girl crew filmed the scenes between Fallon and Olivia on the actual Late Night set.
SAVAGE: We didn’t have a big budget for Gossip Girl at all, so there wouldn’t have been any version of us being able to build their set.
PIZNARKSI: They know their camera positions. They know how to do it. Hilary knows how to do a talk show, obviously, as does Jimmy. She wouldn’t even need direction.
ROSENFELD: For story reasons, we needed to make sure that Hilary said certain things, because that was part of the plot. But as far as writing for Jimmy … I think there was a certain amount of [Fallon] ad-libbing and doing his own thing. At the end of the day, Jimmy Fallon is Jimmy Fallon, and we love him—he’s gonna get to say whatever he wants to say. He does this every day, and he knows exactly what he’s doing, so there’s no reason not to let him say what he wants to say.
In the episode, Olivia is terrified that Dan will be upset about what she said on Late Night. But to her surprise, he ends up taking it in stride, and their relationship comes out unscathed—as a nice touch, Fallon even bakes Dan a “happy anniversary” cake as an apology for embarrassing him.
PIZNARSKI: In retrospect, I don’t know why [Olivia] was so flipped out, because what she said wasn’t terrible. The whole thing was, like, no big deal. I mean, you and I can both think of the things that she could have said to embarrass the sh*t out of him.
ROSENFELD: It was keeping it light. We wanted to protect [Olivia and Dan’s] relationship. We all expected [Dan] to have one reaction. You’re watching and thinking he’s going to be upset about it. But then, with any of these stories, it’s like, “How can we turn it on its head and twist it a little and make his reaction not what we expect?”
Looking back on the episode 15 years later, the Fallon storyline remains a real highlight for the Gossip Girl team.
SAVAGE: I think that the Fallon piece really added a real pop to this story—versus, like, Dan reads in a magazine that Olivia said something bad about him or misconstrues something that she says. That’s a much less fun story. … Looking back on all this, I’m reminded of what a nice connection we had to [Late Night], how special it was to be lifted up and amplified by Jimmy and his team.
ROSENFELD: Hilary was great to work with. It’s funny—I actually was at a school tour for my older kid in LA, and she was sitting two chairs over from me.
PIZNARSKI: Geez, that [episode] was 15 years ago, and Fallon looks the same.
“The Grandfather Part II” (Gossip Girl Season 3, Episode 8) is available for streaming on Netflix, Hulu, andMax.
