Here Are the Worst Times Jay Leno Participated in ‘Alienating’ Political Comedy
Jay Leno believes that late-night shows such as the recently canceled The Late Show with Stephen Colbert lost their way when they started being too critical and “alienating” in their political humor, as opposed to the welcoming and uncontroversial way he called Monica Lewinsky a slut every night on national television.Over the last few days, Leno’s recent and extremely poorly timed interview about the state of late night in 2025 has empowered the online right and enraged the left as the former Tonight Show host declared to the Ronald Reagan Presidential Foundation that today’s late-night hosts are struggling because they picked sides in politics, unlike himself. In case the irony and hypocrisy of Leno claiming that partisanship ruins comedy in a conversation with the Ronald Reagan Presidential Foundation wasn’t nauseating enough in a vacuum, there’s also Leno’s long history of picking sides — usually conservative ones — in his own political comedy stylings that further puts his comments at odds with his actions.“I don’t think anybody wants to hear a lecture. … Why shoot for just half an audience?” Leno lamented of what he perceives to be political side-taking in modern late-night comedy. “I don’t understand why you would alienate one particular group.” So I guess Leno doesn’t understand why he rat-fucked Conan O'Brien and his fanbase either.According to a 2014 study, Leno made more than 4,600 jokes about President Bill Clinton during his time hosting The Tonight Show, which is far more partisan cracks at the President than any other public figure made during the Clinton administration. That, alone, should be a disqualifying piece of evidence in Leno’s claim to have been a “both sides” political comedian, and his accusation that today’s late-night hosts “alienate” half of their audience by calling out President Donald Trump’s war on the freedom of the press couldn’t have come from a glassier house.Additionally, if Leno is really going to claim that “half” the late-night audience are Trump supporters who had to stop watching their favorite comedian Stephen Colbert when he went after the Commander-in-Chief one too many times, how would Leno justify making the disparagement and disrespect of women — and one woman in particular — his entire shtick in the late 1990s?Seriously, Leno was the most sexist, savage and ceaseless critic of Lewinsky, whose affair with her powerful boss when she was 23 years old led to a lifetime of harassment and attacks from right-wing pundits, voters and entertainers. Leno used the public humiliation of a young woman as a weapon in his war against a President whom he disliked, and, out of all the ugliest and most misogynistic attacks on Lewinsky from that ugly era of political “comedy,” Leno’s nightly slut-shaming and name-calling of the disgraced former intern remain the most under-the-belt and mean-spirited examples of what Lewinsky now calls the world’s first cyberbullying campaign.Now, as Paramount sets to silencing any public critics of the President by burning down the very medium of late-night comedy, Leno gets to kick back with his fellow Reagan enthusiasts and pretend that he would never dream of being such a proselytizing pundit like Colbert. But as John Oliver pointed out back in 2019, Leno needs to do some light reading on his own history with politically charged humor — maybe in Oliver’s book, Oh, the Places You Can Go F--- Yourself, Jay Leno!
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