Key Takeaways
- Samuel L. Jackson once roasted Judge Judy Sheindlin for wearing a straw hat in October, telling her, “It’s too late for straw”—and she agreed he was “100% right.”
- Sheindlin says their friendship works because they both “tell it straight,” while Jackson describes her as warm and sympathetic but quick to shut down anyone who mistakes kindness for weakness.
- The pair met in the smokers’ section at a party hosted by their shared agent, Toni Howard, and bonded over Jackson challenging Sheindlin’s Judge Judy rulings.
Samuel L. Jackson apparently knew he'd reached real-friend status with Judge Judy Sheindlin when he felt comfortable telling television's most famously blunt judge that her outfit wasn't cutting it.
Sheindlin revealed the hilariously direct exchange during CBS' Judge Judy: Unfiltered, Unforgettable, a new special marking 30 years since Judge Judy premiered. The longtime friends said their relationship works precisely because neither has much interest in sugarcoating things—and Jackson once demonstrated that by calling out Sheindlin's seasonally questionable choice of headwear right to her face.
"I remember we were having dinner and it was in October," Sheindlin recalled, per Entertainment Weekly. "I was wearing a hat, and he leaned over, and he said to me, 'It's too late for straw.'"
Rather than take offense, Sheindlin cracked up remembering it: "My hat was a straw hat, it was October. He was 100% right!"
That may be about as on-brand as a Samuel L. Jackson-Judge Judy friendship could get. Sheindlin said that despite their seemingly different worlds, they share one major personality trait.
"We could not be two [more] different people, except for one thing—we both tell it straight," she said. "And I can always rely on Sam to tell it straight to me, even if it hurts."
Jackson returned the compliment, describing the woman behind Judge Judy as considerably warmer than her courtroom persona might suggest—but every bit as intolerant of nonsense. "There is warmth and sympathy, but she does not suffer fools," he said, adding that anyone who mistakes "her kindness for weakness" is "instantly put in their place."
Their friendship began, appropriately enough, in the smokers' section. Jackson recalled meeting Sheindlin at a party hosted by Toni Howard, the agent they share. Because Jackson still smoked at the time, he regularly headed into Howard's backyard with the other smokers. Sheindlin was among them, and the two started talking.
Soon Jackson was doing something millions of Judge Judy viewers have probably done from their couches: arguing with her decisions. "I would even ask her about cases," he recalled. "'So I remember that case when you were so and so and you found that person guilty. That person wasn't guilty! The other person was!'"
Instead of banging a gavel at him, Sheindlin laughed. "We became very good friends just having those kinds of talks," Jackson said.
The friendship offers another glimpse of Jackson away from the characters and controversies that have kept him in headlines. This summer, he drew attention after publicly criticizing racism surrounding Argentina during the World Cup.
