“Meghan Markle is an actress, and that’s the difference,” claims Caitlin Reilly of the duchess’ divisiveness, as lunch arrives. “She has a pageant personality.” In front of Reilly is an — admittedly — sad-looking spinach omelet, a singular slice of whole-wheat toast on the side. “This looks so good,” the 33-year-old coos, flashing a grin indiscernible from her more cloying online characters. She’s such a good actress, I don’t know whether to believe her.
Open since 1993, Swingers Diner in La Brea is only six years Reilly’s junior. The actress-comedian frequented the diner as a teen while attending Immaculate Heart in Loz Feliz, the same high school that educated Markle six or so years earlier. Her father — a soap star from the southside of Chicago, and mother — a Swedish model-turned-entrepreneur — conceived Reilly “in a science lab” in the ‘80s. It’s a particularly L.A. origin story, made more so by a childhood in the wealthy enclave of Hancock Park, where homes sell for a median price of $4.1 million. Oscars nights were a family affair, watched with Pink’s hot dogs in hand. The Paul Smith building is next to her chiropractor’s office. A boyfriend told Reilly he would never raise children in L.A., because the city “wasn’t indicative of real life.” They’re no longer together.
For Reilly, life in her hometown has become increasingly surreal. Parodying familiar archetypes on social media has allowed her to amass almost a billion views over the past two years, finding fans in the likes of Reese Witherspoon and securing a regular invite to elite Hollywood events. All that’s missing now, she jokes, is a role on Season 3 of “The White Lotus.”
It was the kind of explosion that would induce whiplash among even the most seasoned entertainers — something Reilly definitely was not. After over a decade of under-delivering agents and failed auditions, she came to the conclusion that her life needed to go in a different direction. At the top of 2020, Reilly took a “big girl” job assisting a real estate agent. When the city shut down three months later during the pandemic, she was out of work again. Worse still, her father’s health was deteriorating — prompting a move back home to support the family. Reilly was 30, unemployed and living with her parents. So, she did what a lot of people in her situation would do — she created a TikTok account.
“I found this random door that I didn’t know existed, and I opened it,” she says. “My number one goal [when it took off] was to start going out for parts. But I was having awful impostor syndrome, like, People only think I’m funny because they have nothing else to do. I’m a hack.”
Ironically, one of the first jobs she booked was a part on “Hacks,” the Jean Smart-led comedy on HBO. Lucia Aniello, one of the show’s creators, watched Reilly’s impersonation video of an “over-active listener” 10 times. Together with fellow producers, she cast Reilly as a TV executive. The role was intended for someone older, but Reilly was “too funny not to hire.”
“Caitlin’s hyper-specific satirization of characters manages to be laugh-out-loud funny without seeming absurdly broad — which is really hard to do,” Aniello says. “She’s hilarious, but in such a well-observed, grounded way.”
Comedy, though, was never Reilly’s intended route. At school, she flailed as a kid diagnosed with ADHD who had dreams of becoming a child actor. Instead of sitting the SAT, 17-year-old Reilly decided to attend acting class and become a “serious” actor — but the industry had other plans.
“I kept getting roles where I was the funny one,” she remembers. “These very character-y, insane roles. I was like, ‘How come I don’t have a romance scene?’ Because you’re funny.”
Reilly attended the American Academy of Dramatic Arts, where she honed her technique with the help of Stanislavski and Meisner (though Method acting is reserved for “a–holes’’ and Daniel Day-Lewis, she quips). After graduating in 2010, Reilly took a series of odd jobs — nanny, waitress — unconsciously composing characters through osmosis. Meanwhile, she tried everything to break through, even attempting to leverage her father’s career. John Reilly was best known for his role as Sean Donely on “General Hospital,” but made cameos everywhere from “Melrose Place” to “Passions.” Unfortunately, in her case, Hollywood’s fetish for famous descendents fell short.
“I kept getting roles where I was the funny one,” Reilly remembers. “These very character-y, insane roles. I was like, ‘How come I don’t have a romance scene?’ Because you’re funny.”
(Mike Jezusko)
“As far as the nepotism aspect of the acting world, [I didn’t benefit],” she says. “The only thing that happened was that my dad died, and then I was on the tribute episode for him on “General Hospital.” When her father died in January 2021, Reilly felt adrift. After years of running in place, the she was finally on an upward trajectory — something he’d never get to see. The juxtaposition of her newfound status against all-encompassing grief was paralyzing. “It just totally f—ed me. Any sense of structure in my life completely went away, and there wasn’t a whole lot of structure.”
The day she woke up to a verified blue check mark next to her Instagram handle, Reilly had a panic attack. In therapy, she realized she had spent so long identifying as Caitlin Reilly the struggling actor that actually “making it” was difficult to reconcile.
“My therapist was like, ‘Who are you? I said, ‘I’m an actor and I’m a comedian,’” she remembers. “I think that’s the problem: there’s so much importance on what you do, that you are what people see you do.”
Who Caitlin Reilly is is a good cousin, she says. She loves nature, and her favorite actress is Elizabeth Olsen. She loves to make her boyfriend, a motion graphic designer, belly laugh. She is outgoing, but “wakes up, lives and goes to bed with anxiety.” Social media doesn’t help.
“I’m incredibly grateful and want to let myself enjoy the experience, but it’s like years ago, I would never have gotten the job,” she says, adding that industry events feel like attending an ex-fiancé’s wedding. “That’s the industry now. ”
Instagram, Reilly believes, has become a necessary evil for those even at entertainment’s highest echelon (“Sydney Sweeney’s entire Instagram is a billboard ad,” she says). Her newfound visibility has only heightened the pressure. One of Reilly’s latest caricatures — a battle-scarred-but-never-beaten waitress in L.A. — managed to reach its real-life source material — the waitress who inspired Reilly’s character. “I genuinely think I was your server,” the waitress commented.
“I loved her, but how the f— did she [find it]?” Reilly says. “Some famous influencers who thought I was making fun of them have blocked me. I wasn’t, I just happened to say things that align with what they did.”
Reilly headlines her own comedy show at the Largo, May 30.
(Mike Jezusko)
“She’s fearless and confessional, her targets are fresh or fresh angles on familiar targets,” echoes David Wain, the writer-director behind “Wet Hot American Summer.”
Wain still remembers “the talent oozing from Reilly in every moment” when he discovered her online, wondering immediately how they might work together. He wasn’t alone. Over the past year, Reilly’s face seems to have graced every major streaming service. She will soon appear in Disney’s “High School Musical” series, as well as a new Max show and the Darren Aronofsky-produced “Little Death” alongside David Schwimmer. RogerEbert.com anointed her a “hot commodity” for her performance in the Apple TV+ comedy “Loot.” On Tuesday, she headlines her own comedy show at the Largo. She’s also writing her own feature — “like everyone,” Reilly clarifies.
“Being thrust into this internet space, I was just white-knuckling it, trying to figure out how I can do what I want to do and be true to myself,” she says.
In-person, Reilly emanates the same truthfulness as her characters. It’s immediately clear she would rather dissect the behavior and habits of others than wax lyrical on her own. The actress self-deprecates readily — even divulging her sister advised her to fill her lips. There’s no faux humility, or strategic attempt at generosity. Returning from the bathroom, Reilly appears genuinely perturbed that I paid for her omelet.
It’s this authenticity that humanizes even the most oblivious of Reilly’s characters. After 33 years living in perhaps the most indulgent city on Earth, she has met them, known them, and maybe even been them. By making them lovably unlikable, Reilly has affirmed her place in Hollywood.
Oh, and Mike White? If you’re reading, “The White Lotus” would look good— so good — with her in it.
