Sherri Shepherd Reveals Her Brief Jail Time Taught Her Life Lessons That Helped Her Succeed

Sherri Shepherd recently opened up about her brief stint in jail because she didn't pay for her tickets. Shepherd shared that her experience behind bars "was a classroom" and a "life lesson" that helped her succeed.

Shepherd has really been succeeding, especially with her talk show, "Sherri," which replaced the "Wendy Williams show." After a first season with guests like Janet Jackson, her talk show has now been confirmed for two more seasons.

Read on to find out more.

Sherri Shepherd says being locked up briefly helped her career success. She recently spoke to Page Six about the eight days she served for owing $10,000 in unpaid moving violations. This happened back in the early 90s, when Shepherd was just starting her career in showbiz.

She said, "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."

Reflecting on her time behind bars, Shepherd mentioned one of the inmates that protected her because she knew Shepherd was "gonna be somebody." She said that the inmate's name was Shelby and that she attended both of Shepherd's weddings when she was finally released.

Shepherd added, "But sometimes people see things in you that you don't see yourself, and when she said those words, 'Sherri is gonna be somebody,' I never thought that for myself. So I just knew that something was going to happen."

Shepherd's career has only gotten better, especially with her new talk show, which premiered last fall after the Wendy Williams show ended. Shepherd had originally filled in for Williams until it was confirmed she'd be unable to return due to multiple health issues.

William's show, which had run for 13 seasons, was then replaced with Shepherd's talk show, eponymously titled "Sherri." At the time, there was some bad blood from Williams, who didn't like being replaced.

Williams reportedly said, "I like her, but I won't be watching her because I know what she's going to be doing and that's really not my thing." In an Instagram Live, Williams spoke to rapper Fat Joe and said, "I love being on my own show, and I love that people love to watch it all the time." Shepherd later briefly commented on Williams, saying, "Wendy is the queen… There's something for everybody."

"Sherri" has been confirmed by Fox TV Stations to return for two more seasons, through 2024 and 2025. David Perler, the executive producer and showrunner will work with Shepherd and Jane Murray in executively producing the upcoming seasons. Shepherd and Murray have since been photographed at an event called "Collabs," per Page Six.

Guests on season one included film star and producer Tyler Perry and singer Janet Jackson. Jackson surprised Shepherd with her appearance on the show, which got the host teary and emotional. Jackson's appearance was part of her promo tour for her upcoming "Together Again Tour."

Shepherd recently surprised her fans with two throwback photos on Instagram. The post included two images, one showing Shepherd in a multi-colored blazer, jeans, red boots, and a huge belt. The second photo showed her in an all-black outfit that featured a hat with gold touches, a large black belt, and chunk jewelry.

Shepherd had the infamous mushroom cut hairstyle in both photos, which made the posts even funnier. Fans flooded the comment section with several hilarious comments on Shepherd's fashion style at the time. Some fans pointed out that she'd looked very good for the 90s fashion, especially with her Wilson's leather pieces.

The caption read, "Today Sherri threw it back to the day of sneaking into clubs in your best Wilsons leather. One fan then commented, "Wilsons leather. When you had a jacket from Wilsons you were the sh*t! I had a blue leather fringe."