Was Julia Louis-Dreyfus Trolling Jerry Seinfeld for Dating Teenagers in This Letterman Bit?

We all love Julia Louis-Dreyfus — sometimes so much that we can’t help but annoy her when she’s trying to pee or give birth. After all, she played iconic characters like Elaine Benes on Seinfeld, Selina Meyers on Veep and Neighbor Who Didn’t Deserve Any of Clark Griswold’s Crap in National Lampoon’s Christmas Vacation.

But one of Louis-Dreyfus’ most delightful roles is Julia Louis-Dreyfus. Whenever she shows up on a talk show, Louis-Dreyfus is always charming and funny. And there’s perhaps no better evidence of this than her many appearances on The Late Show with David Letterman.

Letterman’s official YouTube account recently posted a “Best of Julia Louis-Dreyfus” compilation that, it should be noted, was in no way a harbinger of any tragic news. In addition to her conversations with Letterman, one memorable segment from 2000 found Louis-Dreyfus singing with Jerry Seinfeld. That’s right, singing.

Just two years after the controversial Seinfeld finale, the two actors reunited on The Late Show and, somewhat surprisingly, belted out a number from a famous musical. The segment began with Louis-Dreyfus, alone, on the darkened stage. She’s soon joined by Seinfeld who, at first, seems disapproving and snarky. But then, in a shocking twist, he proceeds to duet with his former co-star. She sounds great, but his singing may be even worse than his Pop-Tart-based filmmaking.

What’s especially interesting about this bit, in retrospect, is the choice of song: “Sixteen Going on Seventeen” from Rodgers and Hammerstein’s The Sound of Music. 

While it’s sung by Liesl von Trapp and her love interest Rolf in the original musical, the song certainly took on a different connotation when performed by Seinfeld, who famously dated a 17-year-old when he was 38. Which was a major scandal at the time, for good reason.

The couple broke up in 1997, just three years before the Letterman appearance. So is it possible that this whole bit was just Louis-Dreyfus’ way of embarrassing Seinfeld? The irony of seeing Seinfeld, who had been called a “cradle-snatcher” in the press just three years earlier, crooning about teenage love must have been hard for audiences at the time to miss. 

It’s hard to say whether or not this was intentional. Louis-Dreyfus had commented on the Seinfeld controversy in the past, but was entirely diplomatic about the whole thing. “No, it didn’t make me cringe,” she told New York Magazine. “When he was in that relationship, it was a happy one for him. And she’s a terribly nice person, so I was in favor of it. Come on — who cares? There wasn’t anything wrong with it. I thought it was great. Anyway, they’re not dating anymore, if that gives other people any happiness.”

I guess we’ll probably never know for sure whether or not Louis-Dreyfus was intentionally trolling Seinfeld by having him play the part of Rolf, who, to be fair, is also a teenager in the musical.