Emmy award-winning comedian Sherri Shepherd has entertained audiences for years on their television screens. The actress, who stars in NBC’s Trial & Error, recently spoke with EBONY about her career, working through fear and if she would ever go back to ABC’s The View.
EBONY: How did you get into acting and show business in general?
Sherri Shepherd: I always used to make my family laugh at our Sunday talent shows. I would do dance moves and make people laugh, it was something that I love. Fast-forward later when I was a legal secretary, we all decided, a bunch of us secretaries, to go to a comedy club. Andrew Dice Clay was on stage and I was making [one of the ladies in the audience] laugh before the show started, she turned around and said to me, “You can do that, you can be on that stage doing that same thing because you’re funny.”
You never know how you will plant a seed in someone’s life; your words are so powerful. Throughout that whole night, I couldn’t pay attention to the comics. Eddie Griffin went up and I thought, “Wow! Can I do that?” I stayed afterward and asked Eddie Griffin, “Do you have any advice?” And he said, “Just get on stage,” and I said, “Well, I’m scared,” and he said, “Well, do it scared.” That’s been my motto for life. 
I started taking comedy classes, and from there I met a guy named Jamie Foxx. I don’t know if you know him or not (laughs), at a comedy club, and he kept auditioning for things, and then I met this guy who kept saying, “I’m going to be in movies!” And his name was Chris Tucker, and a guy named D.L. Hughley. I took some acting classes and I never looked back.
What would you consider your first big break on Hollywood?
There used to be this show called Totally Hidden Video, and they would prank people [and] I played a maid. That’s when I realized when wardrobe asks you what your size is you must tell them the truth. I was a size 16 and I told them I was a size six. I looked like a maid from a porno movie because I couldn’t close the outfit. That was my first big gig, but the first legitimate job was Cleghorne! [starring] Ellen Cleghorne, who used to be on Saturday Night Live. That was the first job that I booked and I was still a legal secretary. My agent told me, “You can quit your job.”
I had that big break . . . and then it was canceled. I lost my apartment, my car was repossessed and I was homeless for a year. I slept on everybody’s couch. In this business, it’s very uncertain. You can be working one day and not working the next.
What kept you going after the show was canceled and you were homeless? What motivated you to continue to pursue your dreams?
I love standup so much and I had to get on stage. It was a need. I am even that way now. I say about three times a week, “I have to get on stage, I have to make people laugh.” I love doing it and it kept me from being depressed that I didn’t have a place to live. Getting on stage made me forget all of that because I can make it funny, and the reality didn’t hit me until I got off stage again.
I never dreamed that I would be on TV, that I’d have a sitcom or that I’d be on The View. It was just like, I needed to be on stage making people laugh or if I book a TV show, I get to make people laugh. It’s a driving force.
What’s the best part of being part of NBC’s Trial & Error?
The best part of being on that show is playing a character that I’ve never played before. I’m a Black woman doing a role that’s so different from what you see a Black woman doing. [Anne Flatch] very nerdy, she looks like she puts her clothes [on] layaway and gets up and irons them every morning, she’s very joyful, she has a high voice, she’s a little naive and to be able to create this character it’s very different. I love this woman. She’s like the heart and soul of the show.
The first season was well reviewed. Any pressure for the second season to live up the first?
We had John Lithgow the first season. How do you top John Lithgow? You get Kristin Chenoweth. She’s hysterical. My character has so many disorders. Are people going to get tired of that in the second season? Is it going to be overkill? Apparently not.
How would you describe your time on The View?
It was one of the best experiences of my life. The first three years I cried in my dressing room [and] it was rough. Barbara Walters was very tough on me. She made me find my voice, she made me learn, I evolved. I didn’t know anything about politics because I didn’t vote. [Now] I am a political junkie, I love politics so much that I can sit and talk [about it for hours]. When I got on The View, I didn’t know anything. It goes down in history, [they] asked me if the Earth was round or flat and I said: “I don’t know.”
I was very naive when I came to that show and I had a tough taskmaster to live up to, but after that three years, it just clicked why I was there, what my role was. I loved it. It opened up the door for so many opportunities for me. I got to do Dancing With the Stars, films and I got to meet President Obama. Of course, Donald Trump was always on there . . . I learned so much, I am very grateful to have had that experience.
Who have you kept in contact with from the show?
Everybody! I text her all the time, Joy [Behar], whenever I’m in town we’d shut down a restaurant, Elisabeth [Hasselbeck] [and I] text back and forth, she was my bridesmaid . . . I know Sunny Hostin very well, Meghan [McCain] used to come on The View. Whenever I go back, it’s like coming home.
Would you go back to The View if asked or take part in another daytime talk show?
I would love to do a talk show. I would love to do what Ellen [DeGeneres] does. I would love to give [her] a run for her money. [Ellen] will go on and do something else, I’d love to take her place and continue. I feel like my training ground was The View because we did politics, pop culture and a lot of different stuff. It’s my dream to do my own talk show.
Would I go back to The View? The answer to that is probably “no.” It’s like when you break up with your boyfriend and then you go sleep with them again and you’re like, “why?”
You were on The View for seven years. Was it a fulfilling experience?
It was very fulfilling, but I felt like it was time to move on. I really wanted to pursue my acting. There’s nothing like booking a job [such as Precious and Barbara Walters walks up to you and asks, “What are you doing? Oh, that’s right, you’re an actress.” I wanted to pursue my acting and I felt like this was the time. Everybody said I was crazy to leave the show. I was leaving a lot of money, the stability of it. I just felt that if I did not do it then, I would never do it. Fear would take over and I’d be scared to leave. I didn’t want to be in fear, I didn’t want to sit in front of somebody promoting their stuff and be jealous because I didn’t have the opportunity.
I stepped out on faith and immediately I got a call from the producers of Cinderella on Broadway. I got to play the evil stepmother, the first African-American to [do the role] and [I did] that with Keke Palmer, the first African-American to play Cinderella on Broadway. I [then] got a call from Will Packer saying, “We got a movie called Ride Along 2, do you want to be in it? Yes!” Had I not got past the fear, I might still be there having a good time, but still yearning for something else.
