Did Jay Leno Babysit Drew Barrymore In Her Younger Days? Here’s What The Former Tonight Show Host Has To Say

As someone who has always admired the rich tapestry of Hollywood stories, I find it truly fascinating to learn about these interconnected moments that bind the industry’s most iconic figures. The tale of Jay Leno babysitting Drew Barrymore, a toddler at the time, is a testament to the serendipitous nature of showbiz, where the roles of babysitter and future talk-show host could intersect in such an amusing manner!


As a dedicated follower, I’m excitedly sharing that Jay Leno recently reminisced about his babysitting days with Drew Barrymore when she was just a toddler. In a special segment on her show, the actress and he engaged in a conversation where Leno, who used to date Barrymore’s aunt, opened up about helping pacify baby Drew during those times. He delighted us with anecdotes about their bond, as the actress expressed curiosity about her childhood self. The comedian also shared some amusing insights from their playtime together, when Drew was just 3 years old.

On The Drew Barrymore Show, as a seasoned veteran from The Tonight Show, I shared an amusing anecdote about our past. “I first met Drew when she was merely three years old,” I reminisced. “At that time, I was dating her aunt. She needed babysitting, so I had the pleasure of picking her up and bouncing her gently on my knee.” I couldn’t help but chuckle as I recounted, “It was simply hilarious.

Simultaneously, Barrymore, seated in a golf cart alongside the seasoned comedian, seemed taken aback by the revelation and queried, “Why didn’t we discuss this before? Can you recall any details about me?

Leno explained, “Back then, I was dating your babysitter, while you were just a toddler. Whenever you’d visit, you’d amuse the child by making them laugh.

As a devoted fan, I’ve always been intrigued by the fact that one of my favorite stars, who graced our screens in “The First 50 Dates,” was nurtured under the watchful eyes of prominent industry figures. Interestingly enough, it wasn’t just the former talk show host who looked after her, but even Pauly Shore once mentioned he babysat Miss Barrymore for a while. Later on, during his time on the show, Shore even proposed to the actress – a moment that left many of us fans in awe!

Furthermore, during the show, Ross Matthews inquired Leno whether he instantly recognized the actress after watching her in various movies and television shows. To this, Leno responded by saying that he initially saw Barrymore in the E.T. movie and thought, “That’s the little girl!” in his mind.

Apart from Leno’s memory of sitting alongside Barrymore, she also reminisced about her debut on The Tonight Show. This episode was hosted by Jay, as Johnny Carson was still the main host, with Jay serving as a guest host at the time. She put it this way: “I think my first Tonight Show appearance with Jay took place when Johnny Carson was still the host and Jay was filling in as the guest host.

Simultaneously, the actress mentioned that Matthews climbed up the industry ladder by doing internships at The Tonight Show, which was then hosted by Jay Leno.

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2024-09-12 21:53