“Widow’s Bay” Star Stephen Root Says He Was ‘Happy to Break’ Henry Winkler’s Emmys Record

The actor made Emmy history with his first win for ‘Widow’s Bay’ and he’s pretty sure the ‘Happy Days’ star won’t mind giving up the record

NEED TO KNOW

• Stephen Root became the oldest actor to win Outstanding Supporting Actor in a Comedy Series at age 74 at the 2026 Emmys on Sept. 14
• He won for his role in the Apple TV series Widow’s Bay, which also broke the record for most Emmy wins by a comedy series for a single season with 14 awards
• Root credited his costars, director Hiro Murai and creator Katie Dipplod with the show’s success

Stephen Root made Emmys history — and he’s pretty sure Henry Winkler is going to be just fine with it.

At 74, the Widow’s Bay star became the oldest actor to win Outstanding Supporting Actor in a Comedy Series at the 2026 Emmy Awards on Monday, Sept. 14, surpassing Winkler, who was 72 when he won the category in 2018 for Barry. 

For Root, who won his first career Emmy for playing boat captain Wyck Crawford on the Apple TV series, the record was a happy one to break. 

“I am happy to break his record. He’ll be happier to relinquish it, I’m sure,” Root told reporters backstage in the press room after his win. 

Root already has an idea of how his fellow Barry actor might react. 

“I’m telling you right now, Henry’s going to call and come and give me a big teary hug because he’s the sweetest man in the world,” he said. 

Root was nominated for his work as Monroe Fuches on Barry in 2019, making his new record especially fitting. However, his win this time around seemed to catch even him off guard. Speaking to PEOPLE after the ceremony, Root said hearing his name called felt “like a mistake.”

“The fact that Widow’s Bay has gotten so much attention from the Academy and all these people is just really heartwarming,” Root told PEOPLE. 

The recognition was also a reflection of what Root sees as the strength of Widow’s Bay as a whole. The dark comedy, which blends horror, mystery and comedy, won 14 Emmys, a single-season record for a comedy series, including Outstanding Comedy Series.

“Well, that’s what I think. This is an ensemble show from production design on down to the actors to everyone. Everyone’s done 110% on this show, and I think we’d be rewarded for that,” Root said backstage. 

He also gave credit to creator Katie Dippold and director Hiro Murai, as well as Matthew Rhys, who stars as Mayor Tom Loftis. Dippold, Murai and Rhys also won individual awards for their work.

“But you’ve got to give it to Katie Dippold who just won, and Hiro Marai for keeping us on the straight and narrow,” Root said. “And the best number one on a show, Matthew Rhys. Yes, sir.” 

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Rhys, 51, was another major part of Root’s experience on the series. When asked which of his costars helped make him a better performer, Root pointed to Rhys and Kate O’Flynn. 

“That would be the combination of Matthew Rhys and Kate O’Flynn, who are now the funniest people on the planet. They’re the subtlest, most beautiful actors,” he said. “The reason I get into shows these days is to learn from people. And Matthew always is a great lesson and it’s so nice to have Kate O’Flynn see her three feet away, just do something with an eye that will knock you over. So it’s that. It’s learning from other people.” 

That spirit of collaboration was part of what helped the cast navigate some of the show’s more out-there moments. Widow’s Bay may have horror, comedy and plenty of chaos, but Root said the cast approached it all with the same goal. 

“There’s an amazing amount of great character actors on this, but as Matthew said at the very beginning, the first table: we’re not doing comedy, we’re not doing a horror show, and we’re not doing a drama. What we’re playing is the truth. The truth and reality. And all those other things come out of that,” Root said. 

He continued, “That’s what I think everybody was on completely the same page, and that’s why we were able to shred the line so well.” 

As for season 2 of Widow’s Bay, Root is hoping to learn more about Wyck and his complicated relationship with Rhys’ Mayor Loftis, including more of the backstory behind the characters viewers came to love in the first season. 

“I’m hoping we’ll get to see more backstory in the second season — of everybody in the show,” Root said. “I think that’s what people love, is they get to love these characters, they want to know more about them.”

Widow’s Bay is currently streaming on Apple TV.

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