Sherri Shepherd On Her Time In Prison: ‘That Was A Classroom’

Sherri Shepherd on Sherri.
(Image credit: Debmar-Mercury)

Sherri Shepherd has been bringing her comedic background to the world of daytime TV since last September, when her talk show Sherri officially replaced The Wendy Williams Show. She had hoped to create a friendly environment, where her celebrity guests wouldn’t have to fear a “gotcha” moment and could instead enjoy a fun and positive experience. It must be working, because Sherri celebrated its 100th episode earlier this month and has been renewed for another season. However, the host knows that without some tough lessons, her current career wouldn’t be possible, and she recently reflected on spending time in prison.

Back in the early 1990s, at the beginning of her career, the standup comedian/actress spent eight days in prison for owing $10,000 in unpaid moving violations. She recalled what that experience taught her, telling Page Six

Yeah, I went to jail for not paying my tickets. At the time I did not think being in jail was a good moment, but looking back I learned to pay all my bills. Jail, that was a classroom… it was a life lesson, and now I pay my bills on time.

Sherri Shepherd has spoken in the past about the struggles she faced in the early years of her acting career, including being homeless for a year and having her car repossessed. Serving time apparently impressed on her the importance of making sure her bills were taken care of, and she credited one of the women she met in jail with recognizing the potential Shepherd had to overcome her circumstances. It’s tough to think that had she not gone through that experience, she might not have gone on to find the success she has today.

It’s not altogether surprising that Sherri Shepherd would take a seemingly negative experience and turn it into a life lesson. In fact, learning seems to be pretty important to the former co-host of The View. When preparing to debut her own talk show — after filling in as a guest host on the final season of Wendy Williams’ show amidst her health struggles — Shepherd sought out the advice of some pretty big names in the interview game.

Sherri Shepherd said she took 15 pages of notes when she met with Oprah Winfrey ahead of her show’s premiere. The Queen of All Media advised the comedian not to worry about the ratings, but rather focus on the energy she put out to her audience. 

The actress was also able to pick the brain of Barbara Walters, her former colleague on The View, who died in December. As Sherri Shepherd prepared to fly solo with her own show, Walters told her to be curious about people and never take “no” for an answer. 

There’s definitely something to be said for Sherri Shepherd listening to those around her — whether that’s Oprah freaking Winfrey or the bonds she formed in jail — and learning the importance of keeping her finances in check is definitely a lesson that has paid off.

Check your local listings to see when and where to catch Sherri in syndication in your area, and be sure to take a peek at our 2023 TV schedule to see what new and returning shows are premiering soon. 

Heidi Venable
Content Producer

Mom of two and hard-core '90s kid. Unprovoked, will quote Friends in any situation. Thrives on New Orleans Saints football, The West Wing and taco trucks.