John C. Reilly has long believed that his career as an actor has benefited from a rigorous resistance to celebrity. Showbiz gossip, tabloid misadventures, stray tweets: These things might help make you more famous, but Reilly believes they detract from the work. “People monetize their privacy these days,” he told me recently. “You have to realize the value of your privacy and protect it.”
This approach has earned Reilly a reputation for being cagey about his personal life. It has also, undeniably, served him well. Now in his fourth decade as Hollywood’s most reliably delightful supporting actor, the 57-year-old is finding a new level of success on television, embracing his sex appeal (and comb-over) in the role of longtime Lakers owner Jerry Buss on this year’s HBO series Winning Time.
Reilly’s son Leo, 23, has an altogether different, which is to say conspicuously more contemporary, idea about the value of privacy. Like his dad, Leo is an artist: He went to college for fashion design, and he recorded music on the side, under the name LoveLeo. As the music earned a sizable following—and a major-label record deal—he dropped out to focus on it. He wasn’t ever quite sure what he’d eventually do for a living, but he knew that reaching his goals would require engaging with his audience in a way his father never had. “I was building a pretty substantial following on social media, and so I knew that whatever I wanted to do, I had at least a little bit of a platform to jump-start and give it a really good chance of succeeding” was how he put it. “I don’t think my parents really understood that quite as much.”
And so, while he accepts the professional utility of social media, Leo admires those who can abstain. “You can do what my dad does and not engage with it. Which is, honestly, the way to fucking do it,” he said. “But at the same time, I came up with a plan to achieve what I want to achieve. And social media is a crucial part.”
The Reillys related this to me over lunch one day in a sun-baked Los Angeles park. Every so often, fans approached John to share their love for his work, but none seemed to clock that the handsome young man with a courageous mustache sitting next to Reilly was his son. This was fine, as far as father and son were concerned. “I want to point out that Leo did the entire thing on his own,” John said of his son’s career. “Nobody knew that he was my son. The record label didn’t know. The people who signed him didn’t know.”
The primary reason that John and Leo’s relationship stayed hidden was simple. “I will chalk that up largely to me looking nothing like him at all,” Leo said. I couldn’t argue with him. John’s face seems to belong to a different century: There is a reason some of his best performances have come in films set in the Old West, or Prohibition-era Chicago, or gang-ruled New York. “I’ve looked like a middle–aged man since I was 18 years old,” he told me, repeating a favorite saying. His preferred outfit—a contemporary take on circa-1890s cowboy fashion—further situates him out of time. As a boy he wanted to straighten his curly hair but was disabused of the notion when a classmate showed up with his own mop straightened. “Even as a sixth grader, I was like, That is the saddest thing I’ve ever seen,” he said. He’s had a fluffy halo of curls ever since.
Leo, meanwhile, more closely resembles his mother (and John’s wife), the producer Alison Dickey, along with his maternal grandmother, whom both men praise for her stylishness. He has wide-set eyes, olive skin, and thick black hair (often dyed a color that doesn’t occur in nature) that he wears pulled back. It’s easy to imagine him modeling, which he’s done a handful of times. He looks like he’s just returned from giving your girlfriend a ride on his Vespa.
So, it was something of a surprise when the internet figured out who his dad was. “Somebody on Twitter a long time ago found that information, and because we look so different it was this whole big thing,” Leo said. And, indeed, for a week or two in early 2020, it was hard to avoid the headlines. “Did You Know About John C. Reilly’s Hot Son?” “Turns Out John C. Reilly’s Son Is a Model, a Musician and Very, Very Hot.” “People Are Losing Their Minds Over Photos of John C. Reilly’s Hot Son: ‘Biology Is Wild.’ ”
Leo recalled that the reaction was quickly followed by vociferous defense of John’s good looks by some of his most ardent supporters. “The general thing that was being put forward was, How is he hot when his dad looks like how he looks?” Leo recalled. “And the overwhelming response was middle-aged women being like, ‘How dare you slander John C. Reilly’s looks! This is one of the most attractive, hot men in Hollywood! How dare you!’ ”
Once, in college, John attended a talk during which a famous actor explained that forging a career in the arts would require single-minded focus. “If you want to be an actor, get ready,” Reilly paraphrased. “No family. No kids. Nothing matters. Nothing can matter except the acting.”
In short order, Reilly learned that, at least for him, this was not true. In fact, being married and having Leo “were nurturing me and sustaining me in my life” as an actor. Accordingly, the home that Reilly and Dickey built was warm, artsy, creative. Phones and electronics were restricted. There were no limits placed on the Reillys’ endlessly replenished boxes of costumes, which Leo immediately took to. “After a while,” John said, “I started noticing that while the costumes were given to him as one thing, he was immediately turning them into all these other things.” The Captain Hook shirt, paired with the bear pants, and accessorized with the pig mask, it turned out, made for a killer outfit.
Leo has more or less carried this approach into adulthood. He showed up to our meeting wearing flared jeans embellished with pink plaid patches, bits of Chuck Taylor sneaker canvas, and actual pieces of other jeans, like a pocket attached below another pocket. He wore a zip-up necktie over his T-shirt, a pair of protective Nerf goggles in lieu of a headband, and blue patent-leather Bathing Ape sneakers. “I have an affinity for things that I liked as a kid that I can repurpose and use now,” he said. “For a long time I used a Wii Nunchuk remote as a belt. Costumey stuff like that makes me laugh.”
It took his father longer to settle into his own style. “At a certain point I realized, you know what, life is short,” John said. “I’ve played all these crazy characters. People see me do these absurd things. They already know that I’m an eccentric person. I am an eccentric person. So fuck it! If I want to dress like a cowboy from the 1890s, that’s what I’m going to fucking do. And it’s going to be okay for everybody because that’s what’s going to make me happy.”
Playing ’80s icon Jerry Buss in his heyday, he explained—wearing silk shirts unbuttoned to the navel, rocking a comb-over with zero apology—had helped too. Inhabiting the famously libertine Lakers owner made it easier for him to understand what his son Leo has known basically since birth: That there is no true self-expression without self-confidence.
John recalled the reaction to his 2002 film The Good Girl, in which he and Jennifer Aniston play husband and wife. Some viewers, he remembered, had a frustrated response: “ ‘Oh, right. Like John C. Reilly would ever be married to Jennifer Aniston,’ ” he said.
Reality, of course, was not quite so simple. Middle-aged men can dress like 19th-century cowboys. Twentysomething TikTokers can speak eternal truths. The funny-looking guy can get the girl and have a hot son. “If you really know about life, yes: John C. Reilly is often married to Jennifer Aniston,” John C. Reilly said, emphatically. “That’s just the way it goes, people!”
Sam Schube is GQ’s deputy site editor.
A version of this story originally appeared int he September 2022 issue of GQ with the title “The Curious Story of John C. Reilly and His Talented Son Leo”
PRODUCTION CREDITS:
Photographs by Jake Jones
Styled by Marcus Allen
Grooming by Catherine Furniss using Stmnt Grooming and Tom Ford
Set design by James Rene
Produced by The Studio Venice Beach