It's Ryan Reynolds' Ad World, We Just Live in It

The first and only time I encountered Ryan Reynolds in person was in the lobby of a hotel in Pasadena, Calif., during a Television Critics Association Press Tour in the late 1990s. The actor from Vancouver, who began his career on the Canadian teen soap Hillside (or Fifteen, as it was known when it aired in the United States), was there to promote Two Guys, a Girl and a Pizza Place (later renamed Two Guys and a Girl). I was there to cover the event, and we were both lost and trying to figure out where to go.

Given his charm and sense of humor as co-lead of the ABC sitcom—which was also evident even while he was lost in a hotel lobby—I was confident that Reynolds had a bright future ahead as a comedic actor. But could I or anyone have predicted that he would become a mega-successful entrepreneur and influencer in the marketing world?

The answer to the question above is ... nope. But when you look at his career path and hear him speak about how he operates, it all makes sense. 

He Can't Stop, Won't Stop

Reynolds starred in lots of movies in the aughts and beyond, ranging from Van Wilder to The Proposal. But it was 2016's Deadpool that elevated him to Hollywood's A-list and revealed his tenacity. 

You see, Deadpool, with Reynolds as the crass antihero from the Marvel comics, didn't simply fall into his lap. The actor worked his ass off for more than a decade to get the first R-rated Marvel film made. While lingering in development hell was, well, hellish, Reynolds stuck with the process because he was confident the film could be a success. His instincts were right. Deadpool had a production budget of just under $60 million and grossed more than $780 million worldwide.

"I've never done a job where I gave my last drop of blood, and this was that," he once reflected in an interview with The Los Angeles Times. "I really felt great about how it was received. It was unlike anything I've ever experienced before just to have the long game pay off that way, sticking with this thing for over a decade and seeing that we weren't crazy, and there was something here."

He Makes Maximum Marketing Effort

Reynolds gave it his all and then some to promote Deadpool, gamely suiting up in costume for promotional appearances and stunts. Seemingly willing to do anything, he even gave Conan O'Brien a massage.

Then there was the prank interview Reynolds did with Mario Lopez to rile up the character's fans, making it seem as though Deadpool was going in a more PG-13 direction.

Reynolds also posted all sorts of creative content related to the film on his Twitter account in the months leading up to its release.

Through the process, the actor, who worked closely on the campaign with George Dewey, then head of digital marketing at 20th Century Fox, developed a new appreciation for the power of promotion. "We started to look at marketing as a completely different tool we had in the shed, and something we could really tell stories with," Reynolds told Entrepreneur.

He Surrounds Himself with Smart People 

Reynolds recognized Dewey's talent and expertise while they were hyping Deadpool, which is why he teamed up with the former McCann Erickson creative to form the production and digital marketing company Maximum Effort in 2018. 

"He was a powerful voice during the campaign, and it was clear his insights extend far beyond marketing," Reynolds told The Hollywood Reporter. "George has a deep understanding and appreciation for what audiences want and how to give it to them. Partnering with him at Maximum Effort is already one of the great highlights of my career."

He Sees No Shame in Selling

Through Maximum Effort, Reynolds continues to bring massive enthusiasm and energy to his role as the brand ambassador for products that are sold by companies that he invested in, including Aviation Gin and Mint Mobile.

It wasn't that many years ago that celebrities didn't want to be seen as sellouts hawking products—they would sneak off to Japan to shoot ads. But times have changed, and Reynolds is happy to be the front man. He flat out kills it nearly every time. His funny, self-deprecating approach actually lulls us into forgetting that he's always trying to sell us something. 

Earlier this month, Reynolds slipped into his pajamas for Bedtime Stories with Ryan. The first show to debut on Maximum Effort's new Fubo channel, the series finds Reynolds lulling us to sleep by reading stories in soft, ASMR-style tones.

But he doesn't really want us to drift off. Otherwise, we'll miss the ads, which are read in whisper voices so as not to harsh the show's relaxing vibe.

He Is a Team Builder

Eager to understand and strengthen his professional connections, Reynolds took a conflict resolution workshop years ago and still applies the lessons that he learned today. 

"We live in a world that's increasingly gamified, and I think we have an instinct to win, crush and kill. But if you can disengage or disarm that instinct for a second and replace it with seeking to learn about somebody instead, that, as a leadership quality, for me, has quite literally changed every aspect of my life," CNBC quotes him as telling the audience at the Indeed FutureWorks conference last year.

Those skills came into play when he and actor Rob McElhenney, best known for It's Always Sunny in Philadelphia, bought the small Welsh soccer club Wrexham AFC in 2021. An FX documentary series, Welcome to Wrexham, chronicled how the pair learned sports management and introduced the team to a worldwide audience.

As with everything he touches, Reynolds' involvement with the team has reaped rewards for everyone involved: Wrexham AFC scored a massive win in April when the team was promoted to the English Football League for the first time in 15 years.