Jay Leno Tells Drew Barrymore That He Babysat Her When She Was 3: “I Was Dating Her Aunt”

Long before Drew Barrymore made her big-screen debut in E.T. the Extra Terrestrial, she was just a kid whose aunt was dating Jay Leno.

On this morning’s episode of The Drew Barrymore Show, Leno surprised his former intern Ross Mathews, who got his “big break” working on The Tonight Show. But Mathews wasn’t the one with whom Leno shared a connection. The legendary talk show host revealed that he first met Barrymore when she was just three years old.

“I was dating her aunt. She was asked to babysit,” Leno recalled. “I picked you up and I bounced you on my knee. It was just very funny actually.”

When Barrymore asked if he remembered anything else about her, he replied, “You were a baby! I was a boyfriend of a babysitter … You just made the kid laugh.”

Flash forward four years and Barrymore made her Tonight Show debut when Johnny Carson was the host and Leno was the guest-host.

Mathews, for his part, started his television career as a Tonight Show intern 23 years ago, before getting promoted to a correspondent from 2006 to 2013.

“My favorite intern. We had a lot of them, but he was the most annoying. That was the fun part,” Leno joked after reuniting with Mathews.

While driving around the studio lot, Leno continued to roast the Drew’s News co-host.

“We enjoyed having you. I always liked you because you were kind,” he said. “I think you started in the mailroom. I don’t mean this in a weird way but you had no discernible talent. I mean, you didn’t sing, you didn’t dance.”

Leno added, “You just had a funny personality. I thought, ‘Well this kid’s got something.’”

The comedian even remembered suggesting Mathews — whom he referred to as the “new annoying guy” — to attend the Ocean’s Eleven premiere.

The Drew Barrymore Show airs on weekdays on CBS. You can check the website for local airtimes.