Jay Leno, legendary chin and all, casually drops a bombshell while cruising around a TV lot with Drew Barrymore and Ross Mathews. You know, just your average Wednesday, driving around, reminiscing about babysitting Hollywood royalty. Because, of course, Jay Leno has stories like that just lying around.
In this totally chill, no-big-deal moment, Jay suddenly goes, “Oh hey, Drew, fun fact: I met you when you were 3.” Drew, bless her, nearly chokes on her own surprise, because what? “Yeah, I was dating your aunt. Babysitting you was part of the deal,” he says, as if he’s talking about picking up a gallon of milk.
Apparently, baby Drew Barrymore, future queen of quirky rom-coms, was hanging out on Jay Leno’s knee while he tried to impress her aunt. You know, typical babysitter’s-boyfriend behavior. Jay casually adds that he was trying to get baby Drew to laugh—probably thinking, “This gig’s gotta pay off in laughs somehow, right?”
Meanwhile, Ross Mathews is losing it, as anyone would. “THAT is so crazy!” he shrieks, trying to process the fact that Jay Leno was basically the first person to try out a tight five on toddler Drew Barrymore. A cultural moment no one knew they needed.
Drew, now fully reeling, asks Jay if he remembered how she was as a baby. Jay’s like, “Eh, you were a baby. What do babies even do? Mostly cry, burp, and maybe star in iconic sci-fi movies later in life. NBD.”
Fast forward a few years, Jay’s sitting in a theater, watching “E.T.” like the rest of America, when suddenly it hits him like a comedic lightning bolt: “Wait a minute… THAT’S the little girl from my babysitting days!” The baby from his past is now saving alien lives and stealing hearts on the big screen. Talk about a “Did I leave the oven on?” moment.
And then, like a scene from a feel-good sitcom, the universe conspires to bring these two back together. Years later, Drew strolls onto The Tonight Show in 1994, Jay’s like, “Hey, I know you!” She’s probably thinking, “Of course you do, I’m famous now,” but little does she know, Jay’s got 3-year-old babysitting stories in his back pocket. And thus begins a beautiful tradition of Drew dropping by Jay’s show over and over until his final bow in 2014.
Jay Leno’s love life has unexpected perks, like babysitting future A-listers, and Drew Barrymore can now add “sat on Jay Leno’s knee as a baby” to her already wild resume. What a small, star-studded world we live in!