Jay Leno recalls meeting Drew Barrymore as a toddler and it’s quite the story: "I was dating her..."

Jay Leno once babysat Drew Barrymore and here’s the heartwarming story behind their unexpected connection
PUBLISHED FEB 26, 2025
Actress Drew Barrymore appears on "The Tonight Show with Jay Leno" at the NBC Studios on September 16, 2003 in Burbank, California. (Image Source: Photo by Kevin Winter/Getty Images)
Actress Drew Barrymore appears on "The Tonight Show with Jay Leno" at the NBC Studios on September 16, 2003 in Burbank, California. (Image Source: Photo by Kevin Winter/Getty Images)

Jay Leno is spilling the beans on his first encounter with Drew Barrymore! While appearing in a September 2024 episode of 'The Drew Barrymore Show', the former 'Tonight Show' host made a jaw-dropping revelation. As per People magazine, Leno revealed that he first met Barrymore when she was a toddler. “I met Drew when she was 3 years old. I was dating her aunt. She was asked to babysit, and I picked you up and bounced you on my knee. It was just very funny," Leno recalled as he toured the CBS lot along with Barrymore and her co-host Ross Mathews. At that point, Mathews was taken aback by Leno's revelation and exclaimed, "That is so crazy!”



 

The 'Charlie's Angels' star then turned to Leno and quipped, "How did we never talk about that? Do you remember anything about me?" In his response, Leno shared, “Well, you were a baby! I was the boyfriend of the babysitter. You would come in and sit and you’d make the kid laugh.” During the episode, Barrymore stated that she didn't remember anything about Leno babysitting her but she did remember the first time she made an appearance on 'The Tonight Show.' Barrymore said, “I believe the first time I did the Tonight Show with Jay was when [Johnny] Carson was still the host and Jay was the guest host."


 
 
 
 
 
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A post shared by The Drew Barrymore Show (@thedrewbarrymoreshow)


 

Later in the episode, Barrymore also mentioned that her co-host Mathews got his first big break as an intern on the NBC talk show 'The Tonight Show.' Then, Barrymore told Matthews, “But I also know what it’s like for a gentleman to take a chance on you and change the life that you know. And for me that was Steven Spielberg, and for you it’s Jay Leno. It’s the deepest, and most meaningful, profound thing.” Following this, Leno uttered, “Well, I’m very proud of both of you."



 

After a while, Mathews wondered whether Leno managed to recognize Barrymore when she appeared in Steven Spielberg's film 'E.T. the Extra-Terrestrial.' For the unversed, Barrymore played the character of Gertie in the 1982 sci-fi movie. As per Today, while having a conversation with Barrymore and Matthews, Leno disclosed that he watched the film and figured, “That’s the little girl.” Decades after, Barrymore and Leno reunited once again when she appeared on 'The Tonight Show with Jay Leno' in 1994. From that point on, Barrymore made several guest appearances on Leno's show before it came to an end in 2014.



 

After the episode was released on YouTube, many fans of the show stopped by the comments section and gushed over the special story. One social media user wrote, "How crazy is that! Wow! What a cool story! Small small world!" Followed by a second user who penned, "That’s so cute!!! Destiny!" A third user chimed in, "Great connections and true meaningful anchors in each other's history." A fourth user commented, "I used to date a car enthusiast back in the late 90's and Hay was always at the meetups on Sundays. At first I was star struck, but then he just became Jay. Very cool guy. Now, if I can only meet my idol....Drew, when can you make that happen?!"

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