The Untold Truth Of Sherri Shepherd

Sherri Shepherd has been a constant presence on television since the 1990s, distinguishing herself as a standup comic, actor, daytime host, and all-around celebrity. When daytime talk star Wendy Williams' health woes forced her to take leave of absence from "The Wendy Williams Show" in the fall of 2021, Shepherd was among the stars who were tapped as temporary fill-in hosts until Williams recovered enough to return, a group that included actors Michael Rapaport and Leah Remini, trash TV king Jerry Springer, and comedian Whitney Cummings.

By February of the following year, it became clear that Williams' medical problems were not as temporary as had been hoped; as a result, reported Variety, Shepherd was selected to become the permanent host of the daytime talkfest, which would be retooled and renamed "Sherri." In making the announcement, Mort Marcus and Ira Bernstein (co-presidents of Debmar-Mercury, which produces "Sherri") issued a statement praising their new host. "Sherri is a natural who proved her hosting skills for many years as a panelist on 'The View,' on Fox's 'Dish Nation' and again this season as a popular guest host of 'Wendy,'" the statement declared, lauding "the unique comedic twist" Shepherd brought to the table. 

TV viewers can be forgiven for assuming they know all there is to know about this multitalented performer, but do they really? To find out, read on for a deep dive into the untold truth of Sherri Shepherd. 

Sherri Shepherd entered show business as a standup comic, but that was more of a fluke than a plan. As Shepherd told the ""People in the '90s" podcast, she was working as a legal secretary in LA when she and some co-workers decided "to do something wild and something different" by visiting famed comedy club The Comedy Store. While watching Andrew Dice Clay, a woman turned to Shepherd, and Shepherd recalled, "She goes, 'You could do that. You're as funny as him.' And it just planted this seed of going, 'Gosh, could I do it?'"

She asked Clay and fellow comic Eddie Griffin for advice on how to break into comedy; they told her to just get on stage and do it. Admitting she was "scared," Griffin gave her some life-changing advice. "He said, 'Do it scared,' which is my mantra for life," she recalled. 

Her early years in comedy, however, were far from lucrative. "Well, I got evicted from my apartment and my car got repossessed ..." she told the Los Angeles Times, admitting she was "broke as all get up." One source of "grocery money" was a weekly contest at a local club, where she regularly won the $100 prize — unless she was up against a Black gospel singer. "You can't compete with that," she quipped. "When I saw a woman walk in who looked like she could sing, I just went home."

While Sherri Shepherd's early years in showbiz were lean ones, she began attracting the attention of Hollywood casting agents. In 1995, she landed a role in a new sitcom built around "Saturday Night Live" alum Ellen Cleghorne. After "Cleghorne!" was canceled after just 12 episodes, Shepherd continued to rack up appearances on the small screen. 

Meanwhile, Shepherd also began studying acting, taking to it like a fish to water. "I loved acting and going to acting class because I liked becoming a person that I was not," she explained to the Los Angeles Times. However, she also contended that those early TV roles tended to be one-dimensional and stereotypical. "It's always the sassy girl," she recalled. "There was a time where if I didn't see the word sassy, I thought they wanted somebody white."

Shepherd persevered, and eventually her roles got bigger and better. As her IMDb profile demonstrated, this included recurring characters on "Suddenly Susan" and "The Jamie Foxx Show," and landing a series regular role on "Emeril," the short-lived sitcom starring TV chef Emeril Lagasse. Then came a high-profile recurring role on "Everybody Loves Raymond" and a starring role in the ensemble cast of TV comedy "Less Than Perfect." As she told the Times, hanging in there ultimately allowed her "more opportunity to do different types of roles ... being in the business as long as I have, people trust me with more. I've proven myself."

In addition to her standup comedy and television work, Sherri Shepherd has also performed on the Great White Way.  Shepherd made her Broadway debut in the fall of 2014, playing Madame in "Rodgers + Hammerstein's Cinderella."

Variety reported on Shepherd joining the show as Cinderella's wicked stepmother opposite Keke Palmer in the title role. According to Variety, that marked the first time that Black actors had ever been cast in those roles in that particular play. 

Discussing her Broadway role during an appearance on "The Queen Latifah Show," Shepherd joked about how she managed to channel the necessary wickedness for the role. "I think about the alimony to the two ex-husbands — I can be evil," she quipped. "But it is such a stretch for me to play evil ..." As a veteran of television, where mistakes made in one take can be corrected in another, Shepherd admitted the live performance aspect of Broadway presented a bit of a learning curve. "It's a different thing, because you don't get a do-over. You don't get to say, 'Oh, I messed up my lines!'" she explained. "My wig came off, and I put it back on and kept doing my lines." 

Sherri Shepherd has been divorced twice, something she's used as comedy fodder in her standup act. But in 2009, she starred in her self-titled sitcom "Sherri," which was based on the true-life experience surrounding her second divorce, which was particularly complicated. "I got a sitcom, 'Sherri,' because I got onstage and talked about how my husband cheated on me with a white girl and had a baby while my son was a child and how we had to make this blended family work," she told the Los Angeles Times. She referenced one part in her act about "wanting to kill [her] ex-husband with a lamp from Target," saying, "I couldn't bash his skull in because the lamp was too cheap — that's why people buy antique lamps, because it's easier to bash his skull."

As Entertainment Weekly reported, the Lifetime comedy was somewhat inspired by Shepherd's life, telling the story of "a woman who invites her husband's mistress and illegitimate child to move in to their house." However, reviews for Shepherd's quasi-autobiographical sitcom — in which she was both star and executive producer — were not great. The Hollywood Reporter's review dismissed the show as "a slip of a comedy," while Newsday criticized its "low-budget" feel as being akin to "a comedy that would have aired in prime time on ABC in the late '80s or '90s." 

"Sherri" was not renewed for a second season. 

Hosting her own daytime talk show will allow Sherri Shepherd to exercise some of the muscles she developed more than a decade earlier on "The View." As The New York Times reported, in 2007, she was invited to be a permanent co-host, following a successful try-out run. At the time, Shepherd was announced as a replacement for previous "View" panelist Star Jones, who'd reportedly been let go from the show. Shepherd went on to spend seven years on "The View" before announcing she was leaving in 2014. 

According to Deadline, the reason for Shepherd's departure was that Shepherd and ABC, which airs the show, were "too far apart" money-wise when it came to renewing her deal. "It's been seven wonderful years on 'The View' and after careful consideration it is time for me to move on," Shepherd said in a statement, sharing her gratitude for the show's creator, Barbara Walters, and her fans, "for supporting me on this journey."

In 2021, to commemorate the show's 25th season, Shepherd returned to reminisce about her time on the show. She explained, "'The View' taught me how to be fearless, because I was so scared all the time when I came here. And I think that's what it taught me, how to be fearless, how to find my voice. I think I came here, nobody knew my name; now when I walk down the street, everybody knows my name."   

Sherri Shepherd was at the center of many memorable moments during her years on "The View" — who can forget the time that she and co-host Jenny McCarthy appeared topless during an episode? However, it's arguable that the most infamous of these came during a discussion about evolution. After Shepherd insisted she did not believe in evolution, co-host Whoopi Goldberg asked, "Is the world flat?" Shepherd offered an odd response. "I don't know. I never thought about it, Whoopi," she replied.

Barbara Walters was incredulous. "You've never thought about whether the world was round or flat?" she asked, with Shepherd responding, "I tell you what I've thought about. How I'm going to feed my child ..." Walters interrupted. "Well, you can do both," she said, with Shepherd continuing, "... how I'm going to take care of my family. The world, is the world flat has never entered into, like that has not been an important thing to me."

When asked by co-host Elisabeth Hasselbeck what she would tell her son Jeffrey if he asked her whether the Earth was round or flat, Shepherd did admit she'd do a bit of research before responding. "I'd look it up," she said.

In 2009, Sherri Shepherd celebrated the publication of her book "Permission Slips: Every Woman's Guide to Giving Herself a Break." The premise, Shepherd explained in an excerpt published by ABC News, was to encourage women to stop being so hard on themselves when they weren't able to achieve the near-impossible goals the set for themselves. As a result, the book encourages women to write themselves the same kind of "permission slips" that schoolchildren receive. "Instead of feeling guilty, let's make it OK," Shepherd wrote.

Discussing how she came to write the book, Shepherd explained the inspiration came from her infamous flat Earth comments on "The View." According to Shepherd, she has a tendency to "zone out" when others are talking, particularly "at the wrong times." This, she said, was the case when co-host Whoopi Goldberg asked whether she thought the Earth was flat, while her mind was racing trying to figure out how a check had bounced and why she was receiving calls from her credit card company. 

It wasn't until after the fact that she realized what she'd said. "The press raked me over the coals," she said. "I felt so badly because I made that mistake." Meanwhile, she'd also "received hundreds of emails" from other women saying they'd made similar gaffes. "And I realized, you know what? Women just need to have permission to say, 'It's okay if I make a mistake,'" she said.

During the second season of bonkers Fox TV series "The Masked Singer," Sherri Shepherd took to the stage costumed as a penguin, singing such songs as Megan Trainor's "All About That Bass," and "The Middle" by Zedd.

When she was finally unmasked, Shepherd discussed the experience in a brief interview for the show. Admitting she was "so scared," Shepherd explained, "Singing is not my forte. I thought I was gonna pass out every single time on the stage, but I did it and I feel really good. I feel like, gosh, I can do anything." 

The biggest challenge she faced was concealing her identity from "Masked Singer" panelist Jenny McCarthy, with whom she'd worked closely when they were both co-hosts on "The View." To keep McCarthy from guessing correctly, Shepherd went to elaborate lengths. "I was doing publicity for a movie that I was in and I had to go to New York before the show started, so I took all kinds of pictures and videos in New York," Shepherd recalled to Parade ("The Masked Singer" tapes in Los Angeles). "So, when Jenny would text me and say, 'Where are you?' I would go, 'Girl, I'm in New York. I'm about to do the 'Today' show.' Then I'd send her pictures of me. I even sent her a picture saying, 'Me, you, and [McCarthy's husband] Donnie [Wahlberg] should have dinner at this place in New York. I'm here right now, it's fabulous.'"

Sherri Shepherd was appearing on the Brooke Shields sitcom "Suddenly Susan" when she landed a guest spot on a far bigger show: playing a museum security guard opposite David Schwimmer and Matt LeBlanc on "Friends." Looking back at the experience for People, Shepherd recalled being "so nervous" on her first day of filming, considering it was television's most-watched show at the time. "Everyone was exceptionally nice to me," Shepherd said. "The first woman that came up to me was Jennifer Aniston." Despite her nerves, Shepherd nailed the performance. She even received a standing ovation from the studio audience! 

However, a few years after that "Friends" guest spot, Shepherd was hit with a huge reality check when "Suddenly Susan" was unexpectedly canceled and she had to start earning a paycheck as a legal secretary again.

In a weird coincidence, she got a job as a temp at the law firm where Schwimmer's father worked. "He had a big picture of the cast in the office, the one where they were all hugging," Shepherd remembered. "He would bring all his clients over and say, 'This is Sherri Shepherd. She was on my son's show.' I was so depressed!" 

Another credit among Sherri Shepherd's impressive list of acting roles is a stint on "The Jamie Foxx Show," appearing in 14 episodes. In fact, Shepherd had known the show's star, Jamie Foxx, long before he became famous, something she discussed during an appearance on the "People in the '90s" podcast. 

As Shepherd recalled, she and Foxx had become friends while they were both struggling comics. Foxx, she explained, was dating a woman who "made him sign a contract that if he made it big, she was going to take like 75% of everything he made." Because Foxx had nowhere else to stay, he reluctantly signed. When that romance crashed and burned, Foxx was flat broke when his ex kicked him out. When the destitute Foxx needed to get a haircut for a big audition (Shepherd thought it may have been for "In Living Color"), she let him borrow $50 dollars — which he never did pay back. "He might deny it to this day. He might act like he don't," Shepherd quipped. "Oh, he might have little memory blasts, but, yes, he does owe me $50."

Shepherd revisited the anecdote while appearing on "Dish Nation," joking that "Foxx "has won an Oscar, he has a platinum-selling album — I ain't never got my $50 back!"

As longtime fans of Sherri Shepherd may have noticed, her weight has fluctuated dramatically over the years. That came to hit home, she told More, when she was diagnosed with type 2 diabetes in 2007, which she attributed to "years eating poorly and being overweight." At the time, she admitted, "I was so overwhelmed. I had no clue what to do. To be honest, I thought it meant eating steamed broccoli for the rest of my life ... I felt paralyzed after getting the news."

Even more alarming to Shepherd was the fact that her mother died at 41 from complications to diabetes, while she counted "multiple family members" who also had diabetes. Her doctor, she revealed, gave her a wakeup call that scared her into taking action, pointing to her "five-inch heels" she was wearing and telling her to "say goodbye because you won't be wearing them much longer with your foot cut off." He warned that if she continued on the path she was on he'd eventually have to amputate her feet. "That sentence alone scared the crap out of me," she admitted. 

That led her to embark on a complete lifestyle overhaul, something she admitted was "one of the most difficult things I had to do!" She then shared the diet regimen she and her doctor had developed in her second book, 2013's "Plan D: How to Lose Weight and Beat Diabetes (Even If You Don't Have It)."

As Sherri Shepherd once told Ebony, she was once so broke that she "lost my apartment, my car was repossessed and I was homeless for a year." 

Those days, however, are far behind her; according to Celebrity Net Worth, Sherri Shepherd is now worth an estimated $10 million. She can attribute at least part of that wealth to advice she received from Rosie O'Donnell, her former co-host on "The View." In an excerpt from the book "Ladies Who Punch: The Explosive Inside Story of The View," published in Us Weekly, Shepherd admitted she was "disappointed" by the salary offer she received to join "The View," given that she was "probably $600,000 in the hole" due to a contentious custody dispute with her ex-husband. 

According to Shepherd, O'Donnell revealed her own salary, and also divulged how much Joy Behar and Elisabeth Hasselbeck were being paid. "They had offered me a salary that was lower than Elisabeth," Shepherd recalled. "Rosie said, 'You're an established actress. Go back and counter with this amount!'" She did, and the network met her counteroffer. Furthermore, O'Donnell advised her to push for perks, which led to ABC paying Shepherd's NYC rent for her first year on the show (a sum of $85,000) along with airline tickets to LA so she could visit her son on weekends. "To this day, if there's a woman who does a talk show, I'll let her know what I make," Shepherd declared.

Being invited to guest host "The Wendy Williams Show" while host Wendy Williams was on medical leave turned out to be a huge opportunity for Sherri Shepherd, ultimately leading to her taking over the show. However, Shepherd was forced to cancel a guest-hosting stint at the last minute due to a medical issue of her own. 

Actor Michael Rapaport, who filled in for the ailing Shepherd, told viewers what had happened. "Sherri was supposed to host today, unfortunately, she had appendicitis," said Rapaport, as reported by People. "She's fine, she is fine, she had to go to the hospital last night for some emergency surgery," he said. "She's feeling fine today and she is resting."

Shepherd had recovered enough to host the following day, and shared a health update with fans on Instagram. "With some alterations this would've been my opening day dress ... but my stomach is swollen from the surgeons removing my appendix," she wrote in the caption accompanying a photo of herself posing in the dress she'd planned to wear. "I tried it on and swore I heard the dress scream 'Bisssshhhh what do you think you're doing!'" 

Back in 2019, Sherri Shepherd was chilling out in the Delta Sky Lounge at New Orleans' Louis Armstrong International Airport when she revealed her presence there was due to a case of mistaken identity. As she shared in a video posted to Instagram, everyone in the lounge thought she was Oscar-winning actor Octavia Spencer — a good friend of Shepherd's. "Octavia, I am in the VIP lounge in the airport in New Orleans," Shepherd whispered in her video. "This guy is really loud. He wants to know why I haven't been nominated for another Oscar this year and now everybody here is wondering why I haven't also been nominated for another Oscar."

However, Shepherd admitted she was reluctant to come clean for fear of losing her sweet VIP accommodations. "People are telling me how much they love me in 'Hidden Figures' and 'The Help,'" she continued. "They think that I am Octavia Spencer, and I can't tell them that I'm Sherri Shepherd because they're going to throw me out of the VIP lounge here at Delta because I used your name to get in."

Subsequently, Shepherd appeared on "Watch What Happens Live," and revealed that her deception took place on the same night as the Oscars, "so everybody kept asking me, 'Why aren't you at the Oscars?'"