Dion Flynn was hesitant to be president. When the actor and comedy writer was first presented with the opportunity to play Barack Obama on Late Night with Jimmy Fallon in 2012, he took it on reluctantly. More than a decade later, Flynn has become one of the most integral and consistent players on The Tonight Show Starring Jimmy Fallon. The former day player is also clocking into the show’s 30 Rock offices full-time.
These days, Flynn serves as a staff writer for The Tonight Show. But he’s been working with Fallon since long before the late-night star was any sort of household name.
The two met back in 1994, when they were both cast members of a local Albany sketch show called Metroland’s Loose Camera. They became friends, and regularly hung out and improvised together. Eventually, Fallon moved to Los Angeles to pursue a comedy career while Flynn, an Army veteran, moved to New York City to attend graduate acting school at NYU. The two lost touch.
In 1998, Flynn bumped into Fallon outside 30 Rockefeller Plaza. Fallon had just left his audition for Saturday Night Live. There was something serendipitous about the encounter; as Fallon quickly explained, Flynn had been a part of Fallon’s audition.
“If you watch that audition, [Jimmy] uses a name, Dieter Gutboots, which is a name that I had invented back when we were in Albany,” Flynn told the podcast In Stitches. “I was so honored that he would use it.”
Several more years passed. As Fallon’s star rose, Flynn put his own career on the back burner. “I began to come really in contact with a lot of demons inside that needed addressing, so I had to put my career and stuff on hold for a while,” he recounted on the podcast. “I’m newly dealing with all this sadness and grief, and things that come up when you first get sober.”
In 2011, Flynn and Fallon crossed paths again. Flynn’s friend, How I Met Your Mother star Josh Radnor, was appearing on Late Night With Jimmy Fallon, and asked him to come along. Flynn hadn’t seen Fallon since that day outside 30 Rock, and wasn’t sure if the comedy star would even take note of him. But that was not the case, as Flynn emotionally recalled on In Stitches.
“[Jimmy] comes into that dressing room, and he said, ‘My god, Dion Flynn. Where have you been?,’” Flynn remembered, choking up. “He said to everybody that would listen… ‘This is one of the funniest guys I know.’”
“He was the Jimmy that people sometimes criticize, because they’re like, ‘How can this guy be so positive?’ But that’s the Jimmy I’ve always known,” Flynn added. “He has an unbelievable source of energy bubbling through him, which you can’t account for in any easily explainable way.”
Soon after, Flynn made his Late Night debut as a cybersecurity expert who, while stressing the importance of strong computer passwords, accidentally reveals his entire password on national TV. The actor went on to play various one-off and recurring characters on the show, including questionable magician The Great Benito and animal expert Randy Williams.
“Eventually, one of the producers looked at the shape of my head, sort of looking at me like I was in a case at a museum,” Flynn tells LateNighter, “and was like, ‘Wait, could you play Obama?’”
That was a loaded question for Flynn. It wasn’t just that he didn’t have an impression of the president. For years, he had actively avoided developing one. When Obama was elected in 2008, a friend of Flynn’s who had written for Saturday Night Live alerted him that the show didn’t have anyone in the cast who could play Obama and was looking to bring in somebody new.
“This is the first Black president,” Flynn told his friend. “I’m not going to make fun of this guy. He hasn’t even stepped out into the space yet. And I don’t know what it would be to make fun of him.”
“All my impersonations up to that point were rooted in derision and mockery,” Flynn explains. “So I didn’t want to do it.”
But by the time a Late Night producer suggested it, something had changed. “Barack Obama comes on the show twice,” Flynn recalled in a story he told for The Moth. “And I see something. He has traits that I love in all of my friends. He can make a joke and he can take a joke. Permission unlocked.”
Seeing the real Obama’s sense of humor, Flynn told Fallon’s producer he was open to mimicking the president. “We’d like to do a camera test on Monday,” they told him.
“That was the worst weekend of my life,” Flynn says, “because I was just stressed out about trying to do [the voice].”
Flynn cracked the code and mastered an impression. He appeared on Late Night as Obama, and days later he did it again. And again. And again.
When Fallon took over for Jay Leno as host of The Tonight Show in 2014, Flynn brought his Obama impression along. He estimates that he has appeared as Obama around 40 to 50 times, as recently as this week. (With Obama on the campaign trail for Kamala Harris this election season, it’s a pretty safe bet Flynn will embody Obama again soon.)
If embodying the president on a late-night show in a matter of days sounds daunting, that’s because it was. “There was a moment when I was nervous,” Flynn admits. “I wasn’t really used to being the only face on NBC, when the camera turns to you. I was thinking, ‘Jimmy likes me. He believes in me. That’s why I’m here. I don’t want to let him down.’
“And then the little red light goes on, and I woke up to something,” Flynn continues. “Jimmy Fallon can love me all he wants, but if I don’t do something here right now that works, all of the love in the world can’t save me. And it gave me this boost… I wanted to meet Jimmy’s trust in me with what I could bring.”
Beyond Obama, Flynn was called in to play a ton of other characters on both Late Night and The Tonight Show, solidifying his place as a utility player who always delivers.
“They would call me and I had to be available day-of,” he tells LateNighter. “And that’s this kind of weird relationship where you say to yourself, ‘Am I too available? Should I play hard to get?’”
But Flynn also found his time with Fallon to be effortlessly enjoyable—something that wasn’t always the case with other jobs he took on. “Back in those days, I could be quite hard to work with,” Flynn admits. “And I never did that with Jimmy and his shows. Always, if it was humanly possible to get there, I would get there.”
“That taught me how much I loved and respected Jimmy and his comedic sensibility,” he adds, “and how much I love playing in the late-night format. That silliness that’s renewed each day with the new news cycle.”
Being an on-call performer for the show, Flynn viewed his role as “100 percent an actor. Occasionally, I would riff,” he says, noting that his history with Fallon gave them a built-in trust for improvising that solidified within the first few years of Late Night.
“I improvise less, now that I really understand and appreciate what the writers put together, than I did before. Because I was not respecting the process enough,” he says. After years of writing comedy himself, doing standup, and doing corporate gigs, Flynn has become attuned to the “careful orchestration” that goes into creating comedy that works.
Over the years, Flynn has portrayed everyone from lawyers to musicians to spokespersons. He continues to recur as Obama, The Great Benito, and meteorologist Ben Dalton. On the episode that followed The Tonight Show’s primetime 10th Anniversary Special, Flynn portrayed the street vendor who briefly hands Fallon a hot dog in the opening credits of the show, demanding the host pay him for 10 years of nightly hot dogs.
It seemed only fitting that Flynn be a part of the show that night, having been such a recognizable part of Fallon’s programs for years. But lately, he’s been brought into the fold even more.
In February, Flynn was hired as a staff writer for The Tonight Show, writing sketches, monologue side-pieces, and material for “joke bucket” segments. “Ten years ago, I turned in two packets. I did a sample of monologue jokes, and then I did a writer’s packet,” Flynn explains. When Fallon took over The Tonight Show, Flynn also wrote and voiced a cartoon depicting a nervous Jimmy encountering the ghost of Johnny Carson. “I think that was my sort of submission, and it just takes whatever time it takes until they’re ready to say, ‘Hey, why don’t you try this?’”
Over those 10 years, Flynn has honed his craft through many different projects. He performs standup, does improv, and tells stories for The Moth that he’s compiling into an audiobook. He even stages a late-night-style show for corporate events. Ever since he began playing Obama on Late Night, he is often hired to appear as the former president at parties, corporate gigs, and—on one profound occasion—a woman’s deathbed. As founder of The Improvisor’s Mindset, Flynn also leads workshops that guide people in applying the basic skills of improv in their personal lives, business, and addiction recovery.
As for his job at The Tonight Show, Flynn is excited for what lies ahead.
“When I look at the list of the bits that I have gotten on, most of them have me in them. I know how to write for my voice,” he says. “I felt self-conscious about it in the beginning. ‘Am I being too greedy?’ But I know what I can carry off.”
That includes co-writing for the characters he’s been performing for years, as well as developing new material—like a Kamala Harris campaign volunteer, and the franchise bit “Kaleid-O-Bility,” in which Flynn breezes through absurdly complex made-up acronyms. In fact, Fallon enjoyed that one so much that he repeated the video a second time during the taping. “What more could you ask for as a late-night writer?,” Flynn says. And just last month, he appeared as himself—writer Dion Flynn—for the first time.
“Part of the job so far has been to notice what the other writers’ specialties are and to try to find my own lane in there,” Flynn says. “And my lane right now is characters who play with Jimmy, because there’s a lot of life in that.”
“To be really honest with you,” Flynn tells LateNighter, “I’m starting to recognize my own value. I’m dizzy, still, with how grateful and lucky I am to be doing this for a living in a way that really supports my family well.”
