Sherri Shepherd Recalls Milo Ventimiglia Being Fired from Unaired ‘90s Sitcom as a Teen: ‘He Was Devastated’

NEED TO KNOW

• Milo Ventimiglia was cast in a 1996 Fox pilot called Rewind, but was let go before filming began

• Still, Sherri Shepherd, who also starred on the unaired series, predicted his future success in Hollywood

• The scrapped sitcom filmed six episodes but was canceled weeks before its scheduled premiere

Before becoming Jess on Gilmore Girls or Jack on This Is Us, Milo Ventimiglia landed what he thought would be his breakout role, but was ultimately “let go.”

In a video shared on Instagram, Sherri Shepherd said that Ventimiglia, 48, was supposed to star in an unaired 1996 Fox pilot called Rewind alongside her and Scott Baio. 

According to Shepherd, the show “was about these two elementary school friends who were grown up, and they had their own advertising business, and whenever they were going through something, they would rewind back to when they were in elementary school.”

Shepherd, 59, was tapped to play Baio’s secretary, and Ventimiglia was cast as the younger version of the 65-year-old’s character, who appeared in all of the flashback scenes. 

Left to Right: Jared Padalecki as Dean, Alexis Bledel as Rory Gilmore, Milo Ventimiglia as Jess in ‘Gilmore Girls’
Credit: The WB

“He was originally at the table read, but then they let him go, and I remember he was devastated, and I said to Milo, ‘You are going to be big,'” she reflected. “Now, I didn’t know he was going to be that big, but he was big.”

Shepherd’s prediction came true not long after, and he “went on to star in This Is Us and he’s now in movies, and he’s working all the time.”

“That just shows you you could be fired for something, but it’s not gonna stop what you got to do,” Shepherd added.

The scrapped show, which also starred Mystro Clark, filmed six episodes before ultimately being cancelled just weeks before it was set to air.

Sherri Shepherd
Credit: John Nacion/Variety via Getty

In February 2026, Ventimiglia reunited with Shepherd on her talk show, Sherri, to talk about the project.

The Gilmore Girls admitted that he was “bummed” after learning they were going in a different direction for his character.

“I was 18 at the time, and it was my first job at Warner Brothers,” he said.

“‘What do I do now? Do I go back to school? Do I go back to waiting tables?'” he recalled thinking.

However, decades later, he still remembered Shepherd stepping up to support him in that moment.

“I remember you told me, ‘Hey, don’t worry about you. You’re going to do great. You’re going to have a nice career.’ “

Shepherd affirmed that she saw him as “a star.”

“I was so incredibly proud every time I would see you book something,” she shared. “And I would tell people, ‘I know Milo!’ Nobody believed me. Like, up until you came on the show, nobody believed that I knew you… [Rewind] never came on, so there’s no pictures anywhere.”

Read the original article on People