What You Didn't Know About Reese Witherspoon's Oldest Son Deacon Phillippe

The late '90s and early 2000s were a golden age for high-profile celebrity couples. From Britney Spears and Justin Timberlake to Ben Affleck's (first) romance with Jennifer Lopez, celeb-watchers had more romantic relationships to root for than ever before. That list also included Reese Witherspoon and Ryan Phillippe, two exciting young actors who had starred together in the 1999 film "Cruel Intentions" and got married that same year.

Several decades later, fans of Witherspoon and Phillippe have two new careers to follow. Their daughter Ava and son Deacon are both in their twenties now, almost as old as their parents were when they got together. There are rumors that Ava's feud with her father is messy, including perhaps a voluntary estrangement, but Deacon seems to be on pretty good terms with the "Gosford Park" star.

Ever since he was young, celeb-watchers have been interested in how Deacon would (or wouldn't) follow in his parents' footsteps. Over the years, he's made a number of attempts to break into various aspects of the entertainment industry, trying not only to honor his parents' legacies but to forge his own path based on his own interests. Read on to learn more about Reese Witherspoon's oldest son, Deacon Phillippe.

Though Ryan Phillippe and Reese Witherspoon's relationship seemed for a few years like a high-powered Hollywood romance destined for the power-couple history books, their marriage unfortunately didn't last long into Deacon Phillippe's life. In fact, he was only three years old when his parents went their separate ways, finalizing their divorce. 

Thankfully, it seems that the former co-stars managed to co-parent well as their kids grew up. In 2014, when Deacon was 10, Ryan told HuffPost that he and his ex-wife had taken their kids to Central Park, swapping memories about filming scenes for "Cruel Intentions" together when they were younger. "There we were with Ava and Deacon talking," he said, "...they were tripping out on the fact that we were there shooting a movie before they were even a thought in our minds." He added that he was happy with the job they were doing raising their children, gushing, "Our kids are incredible. I'm proud of the way we've handled it..."

Ever since Deacon and Ava Phillippe were young, the media has been obsessed that both kids look like the perfect combination of their parents. "Who else are they going to look like?" Ryan mused to ET. He revealed that the unconventional family had conversations about the public's interest in their lives, but he insisted, "We don't sit around talking about how much we look alike."

2020 was a difficult year for most of the world, and Deacon Phillippe was no exception. Still only 17, he told Interview Magazine that he'd switched to online classes, moved to Nashville with his family, and started making music. "I asked my dad about how it works, and he taught me all the stuff he knew, and then I started watching YouTube videos," Phillippe explained. He put out his debut single, "Long Run," that year.

When the world opened back up, Phillippe headed off to New York City to study music at New York University's Tisch School of the Arts. His debut album followed by 2023, and he told People that he'd recorded the entire thing in his dorm room. "That was one of the most challenging things I ever did," he said. "[I] recorded it all in there with my friends, my roommates, while going to school."

He graduated from NYU in 2026, celebrating his accomplishment with a selfie on Instagram. In the caption, he labeled himself, "Coledge grajuit." Reese Witherspoon went into more detail on her own Instagram post about his achievement. "After 4years of hard work, long days, endless papers & classes, working with the greatest teachers and making new friends.." she wrote, "my wonderful son graduated from @nyutisch." She also noted that the graduating class's commencement speaker was none other than her "Big Little Lies" co-star, Laura Dern.

Though Deacon Phillippe graduated from NYU in 2026, his time at the school was not without controversy. When he moved off campus in his second year, Phillippe caused some online discourse thanks to a TikTok some of his followers found tasteless. In the video, the budding musician gave fans a tour of his New York apartment. Though he'd tried to be relatable in the past, it became very clear to his followers that Deacon Phillippe lives a lavish life. After all, the apartment boasted a spiral staircase!

As the discourse evolved — especially as it dovetailed with Phillippe's blossoming music career — people began throwing around the phrase "nepo baby." Thankfully, the college student had a famous father to leap to his defense. Ryan Phillippe told Extra that children of famous parents actually have to learn how to handle so many unsolicited opinions, proving themselves several times over to earn their place in the industry. "You've gotta have a thick skin. There's so much rejection and nasty things that can be said about you," he said. "It's not all celebration."

As for Deacon, Ryan insisted that his son used all of those advantages he'd been given for good. "He's just such a source of light and love, and he's very solid and spiritual," the "Crash" star said. "He's got an incredible work ethic."

As Deacon Phillippe has explored entering the music industry, he's been open about his influences. In addition to crediting artists like Drake for sparking his love of production, Phillippe has also been an outspoken fan of Bruno Mars. It makes sense; Mars wrote his first song at a surprising age, so the young Phillippe now admires the "Uptown Funk" hitmaker's approach to music. "I literally followed him from the very beginning of his career and to this day haven't stopped loving his music," he told Behind the Blinds. "I was hooked from the second I heard 'Count on Me.'"

This is another area where he benefited from having parents with industry connections. When he was a kid, Deacon asked Ryan Phillippe to take him to see the "24K Magic" singer in concert. "It was so special because my dad pulled some strings and I was able to get backstage, where I gave [Bruno] a hug," Deacon reminisced. "I don't think I changed clothes for like three days after!"

Deacon's love of Mars is so strong, in fact, that Reese Witherspoon shouted it out in a since-deleted Instagram post (via Today) marking her son's 18th birthday. "One day he was trading Pokémon cards, singing Bruno Mars songs, and playing 'American Ninja Warrior' in the backyard," the "Legally Blonde" star wrote. "The next day, he is taller than me, cooking the family steaks on the grill and making his own music with his best friends."

Considering how strongly Ryan Phillippe supports his kids trying their hand at the entertainment industry, it's no surprise that Deacon Phillippe has taken several stabs at acting. In 2022, he starred in the S3 of "Never Have I Ever," a show created by Mindy Kaling. His character was named Parker, a member of the debate team who provides an interesting new complication to the show's romantic relationships.

Kaling starred alongside Reese Witherspoon in "A Wrinkle in Time," so she saw the similarities between mother and son up close. "He has the thing that Reese has where he's so warm and just well-raised," the former star of "The Office" told E! News. "Every person, every member of the crew and the cast, he just wants to learn from everyone. So polite, but he's also really funny ."

Ryan even teased his son's acting debut to The List, revealing that his son didn't need guidance because he'd had two great role models. "He's watched his mother and me his entire life," Ryan said, "so there's a great understanding there already." Still, the "I Know What You Did Last Summer" star said he wasn't sure whether this would be his son's chosen career. That decision, he said, would be up to Deacon. "He'll decide how full-on he wants to go in that regard," the proud father explained.

In addition to Deacon Phillippe's forays into music and acting, the Hollywood scion has also found success as a model. In September 2023, he appeared on the cover of ODDA Magazine modeling Celine Homme. The accompanying interview featured a conversation with Ryan Phillippe, and the younger Phillippe hoped to use his born-into-it celebrity status for good. "Hate is just so prominent right now," he said (via Instagram). "I feel a responsibility as a person to attack those things."

Deacon and Ryan also teamed up for a People interview about their mutual love of expressing themselves through clothing. At a J. Crew event, Deacon told the outlet that he wore his father's clothes very often. "When he doesn't want something, he passes it down and usually it's pretty cool," Deacon said. "It's one of the best things about having a dad with good style."

In a separate People interview — this one for an H&M x Rabanne event at which he modeled a shiny silver suit and also performed music — Deacon explained the kinds of clothing that define his style, including his childhood interest in dressing up for church. Influenced, perhaps, by his mother's Southern roots and his own love of New York City, Deacon said, "Just like everything, your life is an amalgamation of all the places you've lived. Same with my style. I like to incorporate a little bit of that country western vibe with a street vibe."

You might expect that the son of Reese Witherspoon and Ryan Phillippe would be an old pro at attending red carpet events, but Deacon Phillippe didn't tag along to major awards shows until he was older. In 2024, he attended the Golden Globes for the first time, accompanying his mother as she supported the cast of her nominated Apple TV+ show "The Morning Show." Witherspoon is often one of the best-dressed stars at the Golden Globes, and that year was no different; while her son opted for a simple, smart tuxedo with a bow tie, the "Sweet Home Alabama" star wore a black gown with pink fabric tied around the bust.

According to Today, Deacon told red carpet interviewers that his mother had given him some simple advice for awards shows like this one: "Gum, hand sanitizer, and be nice to everyone." An interviewer joked about his curfew, and Deacon hinted he may not have one on this particular night. "She's the party animal," he teased. "I'm just gonna try to keep up."

The mother/son outing went viral on social media after a clip surfaced showing Deacon helping fix his mom's hair. This lead to glowing comments from fans online. "So sweet! Her handsome mini me," one person wrote on Instagram, for example. "She raised a gentleman. Rare these days."

Ryan Phillippe supports his son Deacon's love of music, but it's understandable that the "Igby Goes Down" star would be extra-proud whenever Deacon acts. It's even better when they get to do it together. In 2024, they starred in "Motorheads," an Amazon Prime television show about street racing. Part of the show takes place in flashback, and intriguingly, Deacon played the younger version of his father's character's brother. (Got that straight?) Before you cry "nepo baby," however, Ryan insists the concept didn't come from him. "It was the head writer's idea for him to play this part, and I stepped out of the way," he revealed to E! News. "I said, 'Go ahead offer it to him, see what he thinks.' I didn't want to put pressure on anyone."

Although the show's time-hopping construction meant the father/son duo didn't share any scenes, the Phillippe men got to watch each other work. ""I was there through his first night shoot, which was really funny to see him struggling to stay awake at 3:30 in the morning," Ryan told People.

Deacon's part was significantly smaller than his father's, but Ryan savored every chance he got to hang out with his son. They even lived together while Deacon was filming. "Even though I go and visit him in New York, and we spend a lot of time with each other when we can," Ryan said, "it's different than when you've got them in your house every day."

Though Deacon Phillippe has made several attempts to forge his own path, it's clear that he loves his parents and is happy to honor their hefty legacy whenever he can. In 2026, he accompanied Reese Witherspoon to the premiere of "Elle," an Amazon Prime show that serves as a prequel to the world of "Legally Blonde." 

While Witherspoon nodded to her iconic character's love of pink by wearing a lace dress with large, off-the-shoulder sleeves, her son referenced his father's red carpet fashion statement at the 2001 premiere of the original "Legally Blonde." Witherspoon and Ryan Phillippe were still a power couple back then, and he'd made waves with a magenta tie with a pink shirt, aviator sunglasses, and a mohawk. Deacon skipped the shaved head.

Witherspoon didn't re-wear her original dress; after all, she'd just lent it to Lexi Minetree, the actor taking up the Elle Woods mantle for the show. Minetree had worn Witherspoon's "Legally Blonde" premiere dress to an appearance on "The Tonight Show with Jimmy Fallon," and the original Elle Woods explained how it happened (via YouTube). "I have all the wardrobe in storage," she revealed. "She put it on and it fit perfectly. It's like Cinderella's slipper!"