Judith Sheindlin knew Samuel L. Jackson was a real friend when he looked at what she was wearing to dinner and decided not to spare her feelings.
The longtime Judge Judy star recalled the exchange in the CBS special Judge Judy: Unfiltered, Unforgettable. Sheindlin said she showed up to an October dinner wearing a straw hat when Jackson leaned over and told her, “It’s too late for straw,” according to Entertainment Weekly.
Sheindlin burst out laughing while retelling the story and admitted Jackson had been right. “My hat was a straw hat, it was October. He was 100% right!” she said.
The comment captured what Sheindlin says she values about their longtime friendship. Despite coming from very different backgrounds, she said they share one important quality: “We both tell it straight.”
They Met While Smoking at Their Agent’s House
Jackson said he first met Sheindlin at a gathering hosted by Toni Howard, the agent they shared. He was still a smoker at the time and regularly joined a group of guests outside in Howard’s backyard, where Sheindlin was among the people he got to know.
The two began talking about the world and about cases Jackson had watched on Judge Judy. He was comfortable enough to challenge some of her decisions, occasionally telling her that he believed she had ruled against the wrong person.
“She’d laugh at me and we became very good friends just having those kinds of talks,” Jackson recalled in the special.
Jackson described Sheindlin as warm and sympathetic but unwilling to tolerate people who mistake kindness for weakness. “She also does not suffer fools,” he said.
Sheindlin Even Helped Jackson Quit Smoking
Jackson previously discussed their friendship during a 2017 appearance on Watch What Happens Live with Andy Cohen, revealing that smoking had remained part of their early connection until Sheindlin decided to quit.
“When Judy stopped smoking, she made me stop smoking,” Jackson said, according to Bravo. He said she sent him to her doctor in White Plains, New York, and he ultimately gave up cigarettes as well.
Their friendship continued far beyond those backyard conversations. Jackson said they had tea together at the Dorchester in London and had traveled across the country together on flights.
Sheindlin said she can rely on Jackson to give her an unfiltered opinion even when she might not want to hear it. Jackson, meanwhile, has remained comfortable arguing with one of television’s best-known judges about verdicts she handed down on her own show.
Jackson Joined Steven Spielberg and Amy Poehler for the 30th Anniversary Special
Judge Judy: Unfiltered, Unforgettable celebrates 30 years since Judge Judy premiered in 1996, combining Sheindlin’s personal archives and memories with interviews from friends, family members and people who worked with her.
Jackson appears alongside Amy Poehler, RuPaul, former Paramount Pictures chair Sherry Lansing and Steven Spielberg.
Spielberg recalls arranging a mock Judge Judy case for his mother’s 90th birthday because she was such a devoted fan. He and his sister Annie brought a pretend lawsuit against their sisters Nancy and Sue while Sheindlin presided over the family dispute.
The special also features Sheindlin’s son, Judge Adam Levy, as well as relatives, former colleagues and past litigants.
Judge Judy: Unfiltered, Unforgettable aired on CBS on Sept. 22 and is now streaming on Paramount+.