Few in Hollywood have swerved from success to failure and back again (and again) with such relentless optimism as Sherri Shepherd.
From a strict Jehovah’s Witness household in Chicago to legal secretary in L.A. to standup comic to sitcom star to a single episode of Friends to back to legal secretary to recurring roles on sitcoms to standup touring to a movie or two to The View to … well, it’s been a while.
But she’s starting the conversation again. Now 53, with two divorces behind her and a 15-year-old special needs child at home, Shepherd’s in demand, with a return to sitcoms (Mr. Iglesias on Netflix) and talk shows, joining Dish Nation. There’s also a podcast (Two Funny Mamas with Kym Whitley) and, later in the year, a Christian musical — A Week Away — also on Netflix.
Of course, many know her because of The View. Shepherd sums up her time there with one word: “evolution.”
In 2007, Shepherd got a huge break when she joined the talk show created by Barbara Walters. “It was the most painful experience that I've ever gone through, but it was the best experience,” Shepherd tells PEOPLE exclusively. “Barbara was so hard on me. I cried for three years in my dressing room because she was so hard on me, but she did it out of love.” Early on during Shepherd’s tenure at the table, Wendy Williams said on her own show that Shepherd could be “replaced with a potato sack.”
Walters offered her this advice.
"I love you,” Shepherd remembers hearing Walters say. “I just need you to read a book, dear, and learn to defend what you believe. And speak up.”
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Several times Shepherd said too much. Her comments about Christianity and the LGBTQ community in 2014 caused an uproar. Shepherd clarified her comments and apologized on the air. “You love who you love,” she says today. “I’ve evolved. Look, my best friend, my best friend Tommy Borden, he's been married to his husband, Jimmy, for the last 17 years. I couldn't even make two marriages work past six years. Who am I to be judging anybody?"
Shepherd knows she was an inadvertent pioneer into what is known today as “cancel culture.”
“When people wanted to cancel me and take out full-page ads on me and take it outside The View, I would cry. Because I would go, ‘If you knew my heart.’ I came from doing standup and making people laugh and doing sitcoms.” She thinks we all need to slow down and lead with love. “I wish we were a culture of loving and going, ‘Let's just see, hold on before we go, click, your entire life is done, your livelihood. You can never come back from this.’ Now there of course cases where it's just like: You need to be in jail.”
It was also on The View where Shepherd learned how to talk about — and ask for — money.
“I thank Rosie O'Donnell to this day because when I was being asked to join The View, they offered me less than Elisabeth Hasselbeck, who had only done Survivor and worked for Puma, making the tennis shoes," says Shepherd.
That didn’t stop her and Hasselbeck from becoming close. “Now, I love my girl. She was my bridesmaid [at Shepherd’s wedding in 2011 to Lamar Sally, which ended in divorce in 2014]. But there was no way I should have been offered less than Elisabeth Hasselbeck with my credits. I just didn't know.”
Shepherd’s agents at the time, she says, didn’t know either. “It was a small agency. But Rosie O'Donnell called me and she said, ‘This is what I make. This is what Joy makes. This is what Elizabeth makes. This is what you should ask for.’ She helped me negotiate through the entire process.”
It’s a practice Shepherd continues to this day, with a group of close friends and fellow actresses and comics she’s met over the years, organized with Niecy Nash, called Sister Circle.
Shepherd was asked to leave The View in 2014. “I sat in my dressing room in front of the mirror and I couldn't breathe. And I said, 'Lord, I got this child with these challenges [her son Jeffrey], this divorce is coming down the pike. This is going to be bad. What am I going to do?' And there was a small voice, because I'm very spiritual, it's a small voice, it sounds like Barry White, that asked, ‘Do you trust me?’ And I said, ‘Absolutely not. I'm hanging on in my faith by the skin of my teeth.’ And God said, ‘That's all I need.’ ”
Today she leans on God — and she leans on her sisters in the circle. The women with whom she bonded in the audition rooms 25 years ago.
Now, they’re helping a new generation of performers.
“We all get together, Garcelle Beauvais, who I’ve known since the Jamie Foxx Show, and Kim Coles, and Niecy and others. We have dinner and we'll invite a young actress to join,” says Shepherd.
Recently, Dominique Perry from Insecure took part.
“We get together, a bunch of us, just to uplift each other and keep each other going. We talk and talk — about money and kids and my divorces.” She laughs, showing her big smile — and a few tears. “And we listen.”