How Jay Leno Became the Villain of the Last WGA Strike

Talk show host/amateur daredevil Jay Leno made headlines recently after supporting WGA members by popping by a picket line outside of the Disney offices, gifting the striking writers a box of donuts before quickly disappearing from sight like some slow-moving, denim-clad ninja.

Click right here to get the best of Cracked sent to your inbox.

The move earned kudos from some, but others were more critical of Leno — not just because he totally could have afforded to give each striking writer a classic convertible instead of a 99-cent donut, but also because many people saw Leno as the face of the enemy during the previous writers’ strike.

Famously, after the 2007 strike dragged on for months, and into early 2008, both Leno and Conan O’Brien were forced back onto the air by NBC, this time with no writers. This is a little like being forced to make episodes of The Price is Right without fabulous prizes or producing The Bachelor without STI-ridden hot tubs. By the way, this wasn’t done as part of some noble effort to entertain the masses or employ the show’s non-striking crew members; it was specifically conceived by network executives as a tactic designed to “undermine the solidarity of the union.”

The Late Show with David Letterman also resumed production, but Letterman notably returned to the airwaves with his writers. Since The Late Show was owned by his production company, Worldwide Pants, and not CBS, Letterman could look like a hero compared to his colleagues by negotiating a deal with his writers. As the head of Worldwide Pants, Rob Burnett told the press at the time, “We don’t have a problem giving the writers what they are asking for. We think they deserve it, and we’re happy to give it to them.”

Meanwhile, O’Brien and Leno “reluctantly” rejoined the airwaves without their writing staff — as did other hosts like Jimmy Kimmel and Jon Stewart. But what became most confusing and controversial was the question of whether or not the hosts could perform opening monologues. Some reports from the time claimed that there was a “prohibition” on any writing that would “customarily” be done by a Guild member, including monologue jokes. So some hosts, like Kimmel, decided to scrap their monologue altogether for “fear of crossing a line,” but Leno, who himself was a WGA member, did a full 10-minute routine that he claimed to have written himself. 

It went over as well as his starring role in Collision Course. For example, Leno opened with this zinger: “A Jew, a Christian and a Muslim walk into a bar. The Jew says to the Muslim… See, I have no idea what they say because there’s a writers’ strike. We don’t know what they say.”

Or how about this sweaty Bush-era masterclass in cringiness: “They say Al Qaeda is now trying to recruit women. This kind of makes you wonder, what does Al Qaeda promise women to become terrorists? Like men get the 72 virgins, what do the women get? Fifty guys that help out around the house, clean up, cut the lawn, fix the plumbing?” 

NBC asserted that Leno was ethically in the clear to write and perform jokes on the show because he had met with the head of the WGA West, who told him in December 2007 that, when it came to his monologue, “We’re going to look the other way.” A WGA spokesperson denied this, accusing NBC of “trying to stir things up.” The WGA then announced possible plans to “investigate” Leno over the “authorship” of his monologue, inferring that he was lying and had secretly solicited help from other writers in crafting all those aggressively terrible jokes. 

This behind-the-scenes drama also percolated on-camera. When Kimmel uncharacteristically popped by The Tonight Show, seemingly in an effort to create at least a few minutes of watchable, unscripted entertainment (Leno returned the favor on his show), he asked Leno, “Will you write some jokes for me? Because it seems like you’ve got plenty.” Leno responded: “I can’t. That’s illegal.”

Interestingly, O’Brien also performed a monologue, which also had jokes he had apparently written himself. But O’Brien skated by unscathed, presumably because, unlike Leno, O’Brien didn’t just up and pretend like everything was business as usual. Instead, he devoted much of his first monologue to avowing his support for the striking writers and was pointedly still sporting his strike beard, which he once referred to as “a hobby on my face.”

Even Bill Maher somehow ended up looking better than Leno, despite the fact that, on the eve of the strike, he made a statement in support of his own Real Time writers, which immediately careened into a rant about union “witch hunts,” followed by an ill-conceived comparison likening the strike to the invasion of Iraq. (Which at least was very on-brand.) But when Real Time returned to TV, Maher scrapped his opening monologue, specifically because of the “controversy sparked by The Tonight Show.”

A full year after the strike ended, Leno was forced to testify in front of a union trial committee over the allegations that he violated Guild rules. He was ultimately, though, very quietly, cleared of all charges. He got off thanks to an AFTRA clause allowing performers to write their own material and also because multiple witnesses backed up his claim that the WGA had told him it would be okay to perform a monologue when they met at the end of 2007. Leno also “denied working with scabs” and said that the Tonight Show offices even “turned off the fax machines” during the strike, thus preventing people from faxing him jokes for free?

Weirdly, Leno himself didn’t publicize his official exoneration, even though it came at a time when writers were mad at him for a whole new reason. Thanks to its very existence, his short-lived 10 p.m. talk show The Jay Leno Show — the one that kneecapped O’Brien’s Tonight Show — led to “stripping NBC’s schedule of five hours of scripted primetime programming a week,” thus costing WGA members jobs. 

And they didn’t even get any donuts.

You (yes, you) should follow JM on Twitter (if it still exists by the time you’re reading this).