Ryan Reynolds at 50: From late-blooming Hollywood star to near-untouchable mogul

Ryan Reynolds turns 50 this Friday, October 23, but by now he is probably suffering from celebration overload. His daughter Inez celebrated hers on September 30, his other daughter Betty followed on October 4, and his friend Hugh Jackman — practically a member of the family — had his turn on October 12. Besides starring together in Deadpool & Wolverine, the two are also co-owners of BONDS Flying Roos, an Australian team that competes in the international sailing league.

“I’m mostly breathing in helium all day, filling balloons, emptying balloons, filling more balloons. That is Birthday Alley,” the Canadian actor told People magazine in early September. “I don’t like birthdays. I mean, I’m fine with it. I don’t bemoan a birthday, but I’m not like, ‘Hey, let’s have a huge party for me.’ I’m good. I get enough attention.”

Reynolds is a master at managing attention on his own terms. Last July, he strolled through the crowds at San Diego Comic-Con wearing a denim Deadpool suit, disguised as the irreverent antihero he portrays on screen, without fans realizing that the actor himself was beneath the costume many of them stopped to photograph.

“No handlers, no security, no ropes. WHAT A GIFT. Thanks to everyone I met, who aren’t only cosplaying but world-building,” Reynolds wrote in the Instagram post in which he revealed the prank to his 49.1 million followers, one more addition to his long catalogue of good-natured practical jokes.

For decades, his strategy of making fun of everything and everyone, and especially of himself, has served as an effective marketing tool. It has also given him a degree of immunity from public ridicule, rooted in the idea that it is difficult to mock someone who is already joking about his own failures, appearance and past.

“I can read something that says, ‘He should be drawn and quartered.’ I could read something that says I should win a Nobel Prize. Both are meaningless,” he told Time in 2025.

In another example of his absurdist sense of humor, it was the back of his head, rather than his face, that appeared on the magazine’s prestigious Most Influential Companies cover, thanks to Maximum Effort, the production and advertising company he founded in 2018 with George Dewey, which generates more than $36 million in annual revenue.

The Canadian actor began his career at 15 in the teen series Fifteen (1991) and made his film debut two years later in Ordinary Magic (1993). He spent the next two decades moving between romantic comedies such as The Proposal (2009), opposite Sandra Bullock, action films such as the ill-fated Green Lantern (2011), and thrillers including the Spanish production Buried, which earned him a Goya nomination in 2011. But it was the release of Deadpool in 2016, just months before his 40th birthday, that transformed his career and turned him into one of Hollywood’s biggest box-office draws.

Produced by and starring Reynolds, the film was made on a budget of $58 million and went on to gross $782.8 million worldwide. “I think one of the great enemies of creativity is too much time and money. And that movie had neither time nor money,” he told The New York Times in 2024 while promoting Deadpool & Wolverine, the third installment in the franchise, which surpassed $1.33 billion at the global box office.

“I even let go of getting paid to do the movie just to put it back on the screen: They wouldn’t allow my co-writers Rhett Reese and Paul Wernick on set, so I took the little salary I had left and paid them to be on set with me so we could form a de facto writers room,” he revealed.

Money is no longer a concern for him. If his big Hollywood breakthrough arrived as he entered his forties, the past decade has seen him establish himself as an influential business mogul with interests stretching far beyond the film industry. He is co-owner of Welsh soccer club Wrexham AFC, alongside fellow actor Rob McElhenney. In 2025, the club made history by securing three consecutive promotions to reach the Championship.

“Thinking back to that first press conference there and saying, our objective is to make it to the Premier League. And you know, everybody tittering and laughing a little, and that’s okay. I’m not judging them for that. But then now it’s starting to look very, very real,” he told Time.

Reynolds also holds a stake in Mexican club Necaxa, alongside McElhenney and Eva Longoria, and is part of an investor group that includes Michael B. Jordan and owns 24% of the Formula One team Alpine F1. And that’s not to mention the sailing team he purchased with Hugh Jackman in 2025.

Beyond sports, Reynolds acquired a controlling stake in Aviation Gin in 2018 and, after turning it into one of the most sought-after brands in the market, sold it to Diageo in 2020 for $610 million. He pulled off a similar feat with Mint Mobile, the wireless carrier in which he owned a 25% stake, selling it to T-Mobile in 2023 for more than $300 million.

“He takes hefty stakes in seemingly disparate small companies, promotes them — and has them promote each other — with playful quick-turn ads he calls ‘fastvertising,’ and then sells the businesses for millions,” Time wrote in summarizing the formula that has enabled Reynolds to generate substantial returns in virtually every business he touches.

Today, trade publications estimate his net worth at around $350 million, but Forbes noted as far back as 2023 that the companies he either co-owns or has sold have a combined valuation exceeding $14 billion. “I’m so, not at all, an entrepreneur... but I’m very interested in, and pretty good, at emotional investment,” he said at the 2024 Fast Company Innovation Festival.

He also strengthens that connection through philanthropy. In 2023, he donated $1 million to the International Committee of the Red Cross to “help children in Israel and Gaza,” notably avoiding taking sides in the conflict, unlike in 2022, when he donated $1 million to support Ukraine following Russia’s invasion. During the pandemic, he and his wife Blake Lively also donated $1 million to Feeding America and Food Banks Canada. “Take care of your bodies and your hearts. Leave room for joy. Call someone who’s isolated and might need connection,” Reynolds wrote in the post announcing the donation, before adding a trademark joke at his friend’s expense: “Hugh Jackman’s number is ...”

There is no question that Reynolds excels at connecting with his audience, and monetizing that connection. But he is not infallible. The Canadian actor has brought his comic sensibility into the way he shares his family life and, in that respect, has found the perfect partner in Blake Lively, 39. The two regularly trade jokes in public, on red carpets, in interviews and across social media. They met while filming Green Lantern in 2010, when Reynolds was still married to Scarlett Johansson, though already in the process of separating. Their divorce was finalized in July 2011, and by September 2012 he was married to Lively.

“Falling in love is great, but do you like each other? That’s kinda the question you gotta ask yourself, you know, going into it. We’ve always liked each other. We grow together. We learn from each other. So yeah, I’m lucky to have a buddy in that,” he told Entertainment Tonight in 2021.

Over the past decade, not only has his business empire expanded, but so has his family. Reynolds and Lively welcomed their first child, James (11), in 2014, followed by Inez (10), Betty (7) and Olin (3). Parenthood has provided another rich source of material for the couple’s humor. “Being a father is the single greatest feeling on earth. Not including those wonderful years I spent without a child, of course,” Reynolds joked on Twitter in 2016.

It was all laughs until it wasn’t. In the summer of 2024, Reynolds and Lively seemed untouchable. He had Deadpool & Wolverine in theaters, while she was promoting It Ends With Us, and the two films were simultaneously topping the global box office. But those achievements were overshadowed that December when Lively filed a sexual harassment lawsuit against Justin Baldoni, the director and her co-star in the film.

After two years of a highly public legal battle marked by dueling accusations and public smears, the two sides reached a settlement in May 2026. Yet the actress emerged from the ordeal with noticeable reputational damage, something that this time her husband, whom Baldoni also sued for defamation, was unable to deflect with his trademark sarcasm.

“I’m unaware of anybody, frankly, whose wife has been sexually harassed and has made jokes about that type of situation. I can’t think of anyone who’s done anything like that,” Baldoni’s lawyer, Bryan Freedman, said after Reynolds made a light-hearted reference to the dispute during an appearance on Saturday Night Live.

The case also sparked a broader debate about the considerable influence Reynolds and Lively wield in Hollywood, particularly after leaked messages showed the actor seeking support for his wife in ways that some observers described as manipulative. Whether that influence played a role or not, Lively scored her first legal victory on August 27, when it was announced that Baldoni would have to pay her $400,000 in legal costs related to the misconduct and defamation case, though she had originally sought more than $8 million.

Two days earlier, the actress had celebrated her 39th birthday, and Reynolds marked the occasion with an unusually sober Instagram post filled with photographs from their personal life together. “Happy Birthday to the very best human I know. You’re not just another courageous and deeply kind genius. You’re also unreasonably cute. I know how lucky I am that you were born. Every time I’ve ever hit my head, it’s YOUR life that flashes before my eyes,” he wrote.

Otherwise, his social media feed is a showcase of lighthearted moments with Jackman, McElhenney and Kenneth Branagh, who stars alongside him in Mayday. The film was able to shoot several scenes in Budapest thanks to a phone call Reynolds made to the Hungarian capital’s mayor after the production was initially denied a permit.

“One of the obscene luxuries and disgusting side effects of fame is that you can get people on the phone that you otherwise couldn’t. I can take advantage of that, as long as I’m fighting for the side of good,” the actor said, once again using self-deprecating humor to defuse criticism of his influence and power.

Released on September 4, the action-comedy became the most successful film debut in the history of Apple TV+, reaching the platform’s No. 1 spot in 101 countries. It was yet another demonstration of Reynolds’ undeniable ability to channel the attention he attracts in whatever direction suits him best.

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