You know those Progressive Insurance commercials? Comedian Stephanie Courtney has played Flo the Insurance Woman in 215 ads, so far. She’s helped turn Progressive into America’s second-largest insurance company.
She is, by any measure, one of the most successful actors in the world – on television nonstop for 16 years, with face recognition by the public, and the money that goes with it. “I’m not gonna fight you on that!” Courtney laughed. “Even though in my head I’m like, What?”
I asked, “What does it mean when you go out in public? Do people harass you? Want selfies?”
“No, not really,” she said. “Normally I look like a sea hag. So, I get a double life.”
She’s come a long way since 2007: “I was broke as a joke. I was auditioning. I was driving around L.A. auditioning for every commercial, every show.”
Being called a struggling actor, Courtney said, would be a compliment. “I would’ve aspired to be a struggling actor!” she laughed. “And then, I got the audition for Progressive.”
That first ad wasn’t intended to be funny. But then came the ad-lib that changed advertising history: “I remember the first actor, his line after I tell him the whole thing is, ‘Wow.’ And he said, ‘Wow.’ And I’m like, ‘WOW! I know! I say it louder!’ I was kind of shocked at how I screamed in this actor’s face.
“And so, that’s the first clue about, like, who is she, how crazy can she get,” she said.
Viewers loved Flo, and a commercial icon was born.
You may know Dean Winters from his roles on “Oz,” “30 Rock,” or “John Wick.” But you’re most likely to know him from the 150 TV ads he’s made for Allstate. He plays Mayhem, the human embodiment of every risky person, place, or thing in your life. “It’s like, ‘Mayhem, Mayhem, Mayhem, Mayhem!’ I can’t even ride the subway anymore,” she said.
I asked, “Does it bother you at all that you’re getting recognized more for an ad campaign?”
“I think in the beginning, maybe a little bit,” Winters replied. “But I wouldn’t have the lifestyle that I live if it wasn’t for people watching the commercials, watching the TV shows and movies, paying for their insurance. So, every time someone stops me, my first thought is, this person is helping me pay my mortgage!”
The luxury of having a side hustle is not lost on Winters: “It’s a very fickle business,” he said. “You can go six months, eight months without working, easily. A lot of my friends are struggling right now. And so, like, I’m very cognizant of how lucky I am. it’s become, like, the greatest thing that ever happened to me.”
But if anyone knows about the ups and downs of showbiz, it’s Deanna Colon. “I am a 360-degree entertainer, singer, songwriter, vocal coach,” she said. “If you want to be in the world of entertainment, you have to do it all.”
Colon was on “America’s Got Talent,” and she’s appeared in ads for Pepsi and Big Lots. But the biggest break she ever got was the Jardiance commercial.
“I have Type 2 diabetes, but I manage it well, it’s a little pill with a big story to tell!”
“I’m dancing with my mailman and I’m, ‘Hey, how you doing buddy?’ And she’s living her best life!” Colon said.
The ad aired in March 2023. And aired, and aired, and aired. “Apparently they showed it one million times,” she laughed. “People were yelling at me online, ‘I’m so sick of seeing your face!’ And I’m like, ‘I have no power in how much they air this thing, guys!'”
Commercial pay can be pretty good: “With Big Lots, I made over a hundred thousand dollars in a three-month period,” she said. “Plus, you get the health insurance. Yeah, it’s awesome.”
What wasn’t so awesome was the online hate that the Jardiance ad brought her. “I would get emails to my personal website that were horrible, and I’d just be crying,” Colon said. “It was mostly about my weight and how, you know, ‘Oh, if you danced like that all the time, you wouldn’t be the size you are.'”
I asked, “Would you do anything differently now that you know how toxic and horrific some people can be?”
“No,” she replied. “I’m always gonna be a plus-size woman. I’m always gonna be a curvy woman. And you’re gonna see me singing and dancing and acting. The joy of it all far outweighs the haters.”
Meanwhile, Dean Winters will be Mayhem for as long as Allstate will have him. “You know, I really hope that I’m doing it until Mayhem is wheelchair racing in a nursing home, you know what I mean?” he laughed.
As for Stephanie Courtney, she’s given up her youthful dreams of appearing on Broadway or on “Saturday Night Live.” But she still performs every week with The Groundlings improv group.
And she still loves being Flo. “I will tell you, the thing that made my heart grow three sizes that day was the Halloween costumes, seeing, especially like little kids, I love it so much,” she said.
“I’m like, ‘Just keep reapplying powder, reapply your lipstick. Go forth, be free, go spread the word!'” Courtney laughed.
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Story produced by David Rothman. Editor: Joseph Frandino.
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