The Night Jerry Seinfeld and JFK Jr. Discussed ‘The Contest’ on ‘The Tonight Show’

Back in 1998, the stars aligned when Jerry Seinfeld and the dashing attorney from one of America’s longest-standing dynasties, John F. Kennedy Jr., appeared together on The Tonight Show with Jay Leno. As a New York transplant, JFK Jr. jokingly gave tips about the city to Seinfeld, a New York native, and recommended a “great soup place” run by “an ill-tempered guy” (a nod to the infamous Soup Nazi). Leno was sure to keep the Seinfeld ball rolling, too, bringing up the time that John-John was portrayed on the iconic episode “The Contest,” about which member of the Seinfeld gang could go the longest without masturbating.

The exercise in self-denial was spurred by George’s mother catching him rubbing one out to an issue of Glamour. Of course, no contest is exciting without incentive so the crew waged a $100 buy-in, with the exception of Elaine’s $150 bet as she was met with the comically misguided notion that women aren’t as self-indulgent as their male counterparts. 

The episode is responsible for Kramer’s brief but iconic “I’m out,” as the first to fall prey to his primal urges after seeing his naked neighbor. The other three also grappled with their own temptations. For George, there was an attractive, sponge-bath administering nurse. For Jerry, his virgin girlfriend who was finally ready to have sex with him. And for Elaine, it was none other than People Magazine’s 1988 Sexiest Man Alive, JFK Jr., a fantasy that she ultimately surrendered to. While the episode positioned George as the winner of the contest, it wasn’t until “The Finale,” five seasons later, that we learned George cheated, making Jerry the rightful winner. 

Before JFK Jr. even had the chance to watch “The Contest,” he described to Seinfeld and Leno the immediate impact it had on his life despite not being in the actual episode himself (hell, the uncredited actor who portrayed him was hardly in the episode save for an elbow and “his great ass”). “Everyone is like yelling and I’m walking to work,” JFK Jr. explained. “People are driving by in their cars and honking,” prompting him to ask himself, “What’s going on here?” It wasn’t until he got to work, where he served as a Manhattan District Attorney, that someone finally explained seeing him on Seinfeld the night before. 

News of the kinda-sorta cameo even weaseled its way into the courtroom, where the defendant joined the chorus of people claiming to have seen JFK Jr. in the episode. When the attorney rightfully denied having made the appearance, he remembered the defendant leaning over to his lawyer and saying, “The guy’s an actor too. No wonder he’s failed the bar exam,” which JFK Jr. famously flunked twice in 1989 before passing on his third attempt in 1990.  

Seinfeld’s reaction to all of this? The very droll question, “You hadn’t seen (the show)?”