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.

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“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.

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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.

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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.

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