The Stunning Transformation Of Sherri Shepherd

Sherri Shepherd has been the gracing the stages of stand-up comedy clubs and television screens for decades. Whether you know her best as Principal Paula Madison on the Netflix series Mr. Iglesias or you've been following her work since its early days and through her time as one of the co-hosts on The View, Shepherd's career is as varied as it is remarkable. The actress, comedian, businesswoman, author, television personality, and single mom is as hardworking as they come, so even if you don't quite recognize her name, you definitely know her face — and probably her laugh! 

But behind her laugh and sass, there's a lot more to Shepherd's story, including a strict religious upbringing, more than one messy divorce, health struggles, and above all the drive to keep going. To that end, to really get to know Shepherd off the screen, you need to know the full extent of her stunning transformation.

30 years before the first episode of The View aired in 1997, Sherri Shepherd was born in Chicago. Speaking of her childhood on the Journeys of Faith podcast with Paula Faris, Shepherd shared, "I was raised a Jehovah's Witness. We went out in field service every Saturday." But Shepherd said she felt like she was living two lives, the person who would witness on Saturdays and the Sherri she was the rest of the time, "very shy" and "a little nerdy." She even revealed in a 2021 interview on The Kelly Clarkson Show that she ran track in high school. 

Things changed when Shepherd's father was excommunicated from the Jehovah's Witness faith because "he asked a lot of questions and he didn't accept certain teachings." Shepherd was told she wasn't allowed to speak to him, even at home. Her parents ultimately divorced over the ordeal and Shepherd shared that it "kind of was the last straw." Years later, when she was around 19, Shepherd attended a Black Pentecostal church service and was saved. Since then, she told Faris, she turns it all over to God and is a devout Christian.

It's hard to imagine a time when Sherri Shepherd wasn't on television, but her career started very differently. During a sit down with Janelle James for Netflix's Strong Black Lead, Shepherd revealed she was working as a legal secretary when she caught the bug to start doing stand-up. "I was just bored with life, and I said to the other legal secretaries — there was like eight of us — I said, 'Let's do something different!'" 

According to Shepherd, the group went to a comedy show and, while Andrew Dice Clay was on stage, another audience member quipped to Shepherd, "You're as funny as him, why don't you do that?" So Shepherd started taking comedy lessons and doing stand-up, but times were tough. In an interview with the Los Angeles Times, Shepherd revealed the first few years doing comedy weren't exactly lucrative. "Well, I got evicted from my apartment and my car got repossessed," she revealed. But despite the struggles, Shepherd told Ebony that during those early years she met future stars Jamie Foxx, Chris Tucker, and D.L. Hughley. "I took some acting classes and I never looked back," she added.

Once she started acting, Shepherd had small parts on sitcoms like Suddenly Susan and Everybody Loves Raymond before landing a lead role on the ABC sitcom Less Than Perfect in 2002. During the show's four seasons as part of the night time comedy lineup on ABC, Shepherd gained more fame and recognition. In a twist of fate, as Less Than Perfect was coming to a close in 2006, so was Star Jones Reynolds's time on The View. Shepherd originally appeared as a guest host on The View in 2005 and, following the departure of Jones Reynolds, Shepherd became the new permanent co-host in 2007. 

Though Shepherd was overjoyed to be a co-host, she had to make a difficult choice: she feared that the east coast would be too much for her son Jeffrey, who was born prematurely in 2005, so she left him with his father, her estranged husband Jeff Tarpley. Shepherd told People in 2007, "Leaving my baby was the hardest thing," adding, "but this is what I have to do to provide for my son."

Providing for her son also meant that Shepherd needed to take stock of her health, especially after a harsh awakening in her doctor's office. She told Yahoo! Life that after several warnings from her doctors over the years about being pre-diabetic (which she ignored), she was officially diagnosed with diabetes in 2007. "My mom passed away at 41 from diabetic complications," Shepherd told Essence. "I always knew that I had the symptoms but it took a long time for me to go to the doctor." 

When Shepherd finally sought out the advice of a professional, her doctor didn't pull any punches, telling Shepherd she was in for serious complications (like a stroke) if she didn't address her diabetes diagnosis. That's when Shepherd knew she needed to make a change. "It scared me so badly because I had been having the symptoms for a while — the tingling in my feet and my hands, being thirsty all the time and always going to [the] bathroom," she continued. But that scary realization was what Shepherd needed to turn her life around. "Diabetes saved my life," she added.

Being away from her son and dealing with a diabetes diagnoses weren't the only challenges Sherri Shepherd faced while on The View. In her very first week on the show, Shepherd got pulled into a debate about evolution that led to the gaffe heard 'round the world. When asked if she thought the world was flat, she responded, "I don't know," leading to what Time called "media hysteria." 

But alongside all the hate Shepherd received, she told Time that she also received a lot of support from fans, which inspired her. "That's when I realized that we've gotta give ourselves a break or permission to say dumb things and keep moving," she continued. From there, Shepherd's book Permission Slips: Every Woman's Guide to Giving Herself a Break was born. In it, Shepherd takes a comedic approach to sharing stories from her own journey to follow her dreams, while also giving herself permission to mess up sometimes. She told Hip Hollywood in 2014, "I'm hoping that women can read the book and go, 'If this nut can get through it with a smile, maybe I can get through some stuff too.'"

In what the Los Angeles Times aptly referred to as an "expansion" of the Sherri Shepherd "brand" that was starting to take form, Shepherd added to her roster of gigs in 2009 by starring in a Lifetime sitcom loosely based on her own life. The sitcom was called Sherri and told the story of Sherri Robinson, a paralegal by day and actress/comedian by night who is newly single after her husband cheats on her and gets the other woman pregnant. 

At the time this show was airing, Shepherd was going through a divorce from husband Jeff Tarpley, who had – you guessed it – cheated on Shepherd and gotten the other woman pregnant. Although the sitcom lasted for only one season, The Hollywood Reporter called Shepherd's performance "quite fun to watch," while Newsday gave it a B and contended, "If you're just seeking a few (sometimes cheap) laughs, Sherri provides." Talk about turning something dark into an opportunity.

Sherri Shepherd's son Jeffrey was born prematurely in 2005, and weighed less than 2 pounds at the time. As a result, he suffers from developmental delays. To that end, Shepherd shared on the CBS Early Show that she didn't know where to turn to get him help when they moved to the East Coast. "When we got out here to New York, he was only able to speak in two word sentences," she explained. Fortunately, that changed thanks to YAI, a non-profit that offers services for children and adults with special needs. 

Shepherd has since become a spokesperson for the organization, helping them to raise money to keep their services up and running. "I don't know what I would have done without YAI," she shared in a video for the organization. "Just to see my son and see where he was when he started [before YAI] and where he is now, I just have this profound sense of gratefulness."

Despite a steady job as co-host on The View, Sherri Shepherd branched out again in 2010 to become the host of The Newlywed Game, in addition to her gig on The View. Shepherd replaced Carnie Wilson and helped navigate the show as it moved networks (via the Los Angeles Times) from GSN to Bounce. Additionally, during her time on the show, Shepherd herself became a newlywed again, marrying Lamar Sally in a televised special in 2011. 

Although wedding bells were ringing for Shepherd, she was still paying for her previous divorce; though Essence reported at the time that Shepherd was bringing in over $50,000 a month even before her hosting gig on The Newlywed Game, the reality was a little more grim. In a 2019 appearance on the Karen Hunter Show, Shepherd revealed that despite having two lucrative jobs, she was struggling due to financial difficulties stemming from her first divorce. "When I was doing The Newlywed Game, y'all, them checks were going straight to the attorneys," she confessed.

As she worked to make enough money to pay her divorce attorneys by hosting The Newlywed Game and The View, Sherri Shepherd also decided to try something new: dancing! After taking dance lessons prior to her 2011 wedding, Shepherd took the plunge and joined the cast of the 2012 season of Dancing with the Stars. However, doing so required some sacrifices, including red eye flights so she could juggle DWTS and The View. How did Shepherd manage it? As she told The Hollywood Reporter, "I work for a woman named Barbara Walters and she has taught me well about how to handle more than one thing." 

Though she was considered a fan favorite, Shepherd and her partner Val Chmerkovskiy were eliminated in the fourth week. Calling it "a dream" to be on the show, Shepherd left the competition with inspiring words for fans. "That thing that scares you the most that makes you say, 'I don't know if I can do it, I'm scared,' — run towards it because it's so amazing on the other side," she shared through tears.

Though it had taken Sherri Shepherd a while to take her health seriously, after her diabetes diagnosis in 2007 she realized that the lessons she was learning were important to her community as well. That's when she partnered with her doctor to write Plan D: How to Lose Weight and Beat Diabetes (Even If You Don't Have It). 

Not long after the book was released, Shepherd sat down with Good Housekeeping to talk about why she wrote it in the first place. "I decided to do it because diabetes is a top killer, especially in the African-American and Latino communities," she explained. "I know the struggle of changing your eating habits and making exercise part of your life. I wanted to inspire people to turn their lives around and feel good." 

It turns out that just as much as Shepherd wanted to share her story, others wanted to read it and learn from her. According to Shepherd's website, the book hit #13 on the New York Times Best Seller list.

In 2014, Shepherd was going through a messy split from her second husband, Lamar Sally, and was fired from The View. To say it had the makings of a terrible year would be an understatement, but if there's one thing we've learned about Sherri Shepherd, it's that she doesn't give up. In September 2014, Shepherd added Broadway star to her resume when she joined Rodgers & Hammerstein's Cinderella as Madame, Cinderella's wicked stepmother. According to Queen Latifah, Shepherd was the first African-American woman to play the role on Broadway. 

If a historic Broadway role wasn't enough, Shepherd also added Cooking Channel host to her list of accomplishments after The View. In 2015 she became the host of Holy and Hungry, a show that found Shepherd traveling around New York and New Jersey to restaurants owned by people of faith, combining her love of food with her love of God. Holy Schnitzel! The show only lasted for six episodes.

Although Shepherd took control of her health after her diabetes diagnosis in 2007, the star turned heads again after posting an Instagram photo in late 2018 looking more fit than ever. The caption of the photo revealed Shepherd was following the keto diet, helping her lose over 25 pounds. "This is not a fad — it's my life that is at stake," she proclaimed in the caption. 

The journey is paying off in dividends: Shepherd revealed in a May 2019 Instagram video that she's no longer diabetic. "The doctor said to me, 'You're not even prediabetic, what did you do?'" she shared excitedly. "I know it's because I've been off sugar since March 2018." 

Though Shepherd is committed to her healthy lifestyle, she knows that there are ups and downs when it comes to health and fitness. In an interview with iVillage, Shepherd revealed that even though she's worked hard to be healthy, it's going to be a lifelong journey. "I think until the day I leave this earth, I will struggle with my weight," she shared. "Life is all about readjustment. As long as I can readjust, I'm good."

Speaking of readjusting, Shepherd was doing more in 2019 than working on her health: she pivoted and began hosting Game Show network's Best Ever Trivia Show in 2019. In an interview with Entertainment Tonight, Shepherd said she was having the time of her life. "I watch every trivia show there is, so to see the experts who I know from different shows and to actually be a part of it, it's very exciting," she gushed. 

While hosting a trivia show isn't as difficult as being on one, Shepherd doesn't shy away from challenges; in late 2019, Shepherd was revealed as The Penguin on the second season of The Masked Singer. In a follow-up interview on Access, Shepherd opened up about the experience. "I said yes 'cause it scared me," she confessed. "To get out there and sing, I was so scared." 

But even beyond the singing, the hardest part may have been keeping it secret, especially from judge Jenny McCarthy. "She knows my walk, she knows everything about me, so it was extremely difficult," Shepherd added. And at the end of the day, McCarthy nailed it.

The 2020 pandemic resulted in a pause for much of the entertainment industry, including live comedy, television show tapings, and movie filming, leaving many in the industry without consistent work. But that didn't stop Sherri Shepherd! In August 2020, Shepherd came on board as one of the L.A. hosts of the entertainment comedy show Dish Nation. "I jumped at the opportunity because we are in a pandemic," She told TV Insider. "It wasn't like I was going to make a movie with Forest Whitaker right now." 

Never content with doing just one thing at a time, Shepherd also started a podcast with her friend and fellow actress/comedian Kym Whitley called Two Funny Mamas, which was years in the making. "For three years she said no to me about a podcast," Shepherd said about Whitley. "I guess during the pandemic she had a lot of free time. Now she loves it." 

Shepherd also scored a recurring role (via Deadline) on ABC's Call Your Mother, which premiered in January 2021. We've certainly not seen the end of Sherri Shepherd. In fact, it seems like she's just getting started.