Jay Leno Ruined His Already Soured Reputation & It Had Everything To Do With Monica Lewinsky

In what was possibly an attempt at clinging to his remaining shards of relevance, comedian Jay Leno sat down with the Ronald Reagan Presidential Foundation for an interview in July. Speaking with president and CEO David Trulio, Leno bypassed any conversation about his own rookie mistakes, and instead pointed out the flaws he finds in the current swath of late night television hosts. The former "Tonight Show" host bemoaned what he sees as comedians getting too political on a near constant basis. Leno suggested that comedians nowadays have to be "content with half the audience, because you have to give your opinion." Leno warned against "cozying" up with just one side of the political spectrum before insisting, "I like to bring people into the big picture." However, anyone who witnessed Leno's performance on "The Tonight Show" during the 1990s will remember one person he often brought into the big picture for all to laugh at — Monica Lewinsky.

"Didn't you spend half your career mocking Monica Lewinsky?" asked one user on X. In 1998, then-President Bill Clinton was awash in scandal as his extramarital relations with then-intern Lewinsky was at the center of a televised impeachment trial. The salacious details of their intimacies became late night fodder fuel, and Leno was one of many comedians who made nonstop jokes about what ended up being a rather traumatic period for Lewinsky. Which is why it feels a bit disingenuous for Leno to be casting stones at other comedians when much of the general public remembers him capitalizing on such a divisive political moment.

While Jay Leno didn't name any names, the airing of his interview did coincide with the news that "The Late Show With Stephen Colbert" had been cancelled. Colbert, and other late night comedians like Jimmy Kimmel and Seth Meyers, has often had political jokes as part of his shtick. Of course there's the ongoing feud between Leno and David Letterman, but despite Leno's claims of nonbias, there's some proof that he wasn't as down the middle as he assumed.

According to an analysis from George Mason University, Leno told at least 450 jokes about Lewinsky during his tenure — which seems small, due to what felt like unrelenting comments being made nightly about her. However, the same study turned up a whopping 4,468 jokes at Bill Clinton's expense, and one can assume that though Lewinsky wasn't named in them, that she was the butt of many of them.

Regardless of the data, the court of public opinion is full of people "old enough to remember Jay Leno going after Monica Lewinsky for years," according to a commenter on X. In response to Leno's insistence that being political will "alienate" audiences, another user wrote, "Leno always alienated me because he's not funny...did he not think mercilessly going after Monica Lewinsky were not 'political jokes'?" While Lewinsky has successfully aged out of the scandal and into her own person, it seems that Leno would also like to forget all the times he dunked on her.