Tina Fey And Amy Poehler Proved Jay Leno's 'Tonight Show' Was "Boring" As He Fumbled With His Questions

Highlights

Fey and Poehler’s comedic charm saved Leno’s interview with their funny anecdotes and energy, proving his Tonight Show formula to be a bust.
Leno fumbled with questions, making Fey and Poehler shine brighter, especially during their SNL “Weekend Update” team-up discussions.
Despite Leno’s “boring” and “creepy” reputation, he remains the richest late-night host with a net worth of $450 million.

In 2004, Jay Leno was privileged to interview Saturday Night Live‘s then-new favorite duo, Tina Fey and Amy Poehler. At that time, the latter had just replaced Jimmy Fallon on the show’s “Weekend Update” segment, making them the first all-female “Weekend” team. But instead of celebrating that, fans noticed that Leno was “unprepared” during the episode.

Thanks to Fey and Poehler’s comedic chaps, they managed to carry the show while the host fumbled with his questions. Back then, Leno had a reputation for being both “boring” and “creepy” despite beating David Letterman‘s ratings during their famous late-night rivalry. Here’s how the Mean Girls stars proved that his Tonight Show formula was a bust.

The interview started on a high note. Leno was upbeat, while Fey and Poehler were matching his energy. The host then asked where the “old friends” met before SNL. “We met in Chicago. We were in an improv group together at ImprovOlympic,” Poehler said, before joking it was “50 years ago” and they’re “68 now.” Fey then had the audience laughing when she said their team’s name, Inside Vladimir, was inspired by a gay porn flick.

“We were named after a gay porn movie that was for rent at the mini-mart where we used to live,” she said. “We didn’t know it was a gay porn movie like the first two times we watched it.”

Leno responded with a dry, “Really? [You] probably grew up sheltered.” It wasn’t that bad, but it didn’t get any better either. After the story, the host made an awkward pivot by asking them if they had made any money from those days. Fey said they didn’t as they only did improv in chicken wing restaurants. But Poehler saved the dead-end topic by sharing they “used to tour across Texas in a van,” which made the audience applaud.

The actress also used to make jingles for their future sitcoms back then. “We made like $30 a week,” Fey said of their tour. In an almost gibberish manner, Leno asked if the “girls” tried to negotiate their rates. But the women said they still kept their day jobs to support their comedy careers.

For instance, Poehler worked at an “old-timey ice cream shop where Rachel Dratch, also on the show, worked.” Unfortunately, The House actress had sleazy guys taking advantage of their free birthday ice cream, which came with a birthday serenade from her while “banging a drum” and wearing an “old-timey outfit and a boater hat.”

“The frustrating thing about that restaurant is you couldn’t make anybody prove it was their birthday,” Poehler recalled. “… It’d be like three guys being like it’s my birthday and you’d be like, ‘Really?’ And then you turn, another guy be like, “It’s my birthday too. Yeah, it’s my birthday I want a free sundae and
hold my nuts
.”

Leno had yet another blah response. Luckily he didn’t get as creepy, but the actress definitely carried that loudly applauded moment. He attempted to redeem himself by telling Fey she doesn’t look like the “food server type” because she “doesn’t seem to have the patience,” to which the guest said, “Thank you,” anyway. But as it turned out, she also had an awful experience with men while working at the YMCA.

“[My] first time at Chicago, I worked at the YMCA which was a residential YMCA where dudes were living there and stuff and my shift was 5:30 in the morning till 2:00 in the afternoon… It was just like a bunch of dirtbag, you guys, being like, ‘Yeah, did my chick come yet?’ [And I’m like], ‘No Randy, come back in an hour.'”

With so much material coming from the guests’ side, and hardly anything from Leno, a fan wrote in the comments of the clip above, “Leno is so stale.” Another viewer was nearly bored to death as well. “Wow Leno is realllyyyy bad,” they said. “They’re saying interesting things and then he asks them something so banal I want to die.” Someone also thought it was “ridiculous” such performance ended up on The Tonight Show, saying:

“Leno can make interviews with funny people like Tina Fey and Amy Poehler seem so boring.”

Tina Fey has an estimated net worth of $75 million, while Amy Poehler has $25 million.

Jay Leno Seemed Fumbled In Asking Amy Poehler About Her Major ‘SNL’ Team-Up With Tina Fey

Moving on to the main moment—Poehler’s team-up with Fey for SNL‘s “Weekend Update”—Leno struggled to compose his question, asking the former: “How did you… How were you chosen? Well how many people…? Do a lot of people audition to this? Do you…?” Luckily Fey saved him and made the audience laugh by chiming in, “Over 10,000 people,” in reference to the audition inquiry.

Poehler then quipped, “It was just like your basic kind of hell week they put me through,” with her collaborator saying there were “a lot of physical challenges, written tests,” as well as “passing eggs with your neck,” per Poehler.

By this point, it was as if the audience was just laughing the entire show—only because of the guests. “Sheesh, Jay seems really unprepared here,” a fan noticed. True enough, Leno fumbled with his follow-up question, again. “How far ahead… Like, did… How far ahead did you know [about the team-up]? Was it a month before? Was it two months before?” Poehler said she learned about it just the Monday before.

“I actually was happy about [the last minute notice] because you know Tina and Jimmy were so fantastic on that show together, and it was a really hard spot to fill,” she revealed. “And Jimmy is so great, and if I had known about it all summer, I would have really, over-you-know, just panicked about it. So I was happy.”

Leno tried to get on the duo’s level by asking if they received “annoying network notes” like, “We’re not sure if a blonde could work in that spot.” The actresses gave him a little filler laugh as the audience stayed silent. Fey got the crowd cheering again when she dramatically said, “Jimmy was my comedy husband right? And when he left me, I felt like I couldn’t, you know have another man in the seat.”

She then hilariously compared the team-up with “when Bea Arthur moved in with Rue McClanahan on the first episode of Golden Girls.” Leno said he didn’t get the iconic reference, reaffirming his poor track record with handling female guests. “Yeah I missed that one, but I know what you mean,” he said, sounding like he’d already checked out from the interview.

Leno even got roasted for his stand-up comedy. Somewhere in the show, Poehler said, “I don’t come from the world of stand-up, [so] it’s very difficult to kind of have your face on there, and you’re telling a joke, ‘Here’s my joke and this is my face.'” Leno then consciously asked, “Is that what I do?” to which a fan said, “Actually Jay, it kind of is…”

Here are Leno’s five creepiest moments with female guests on The Tonight Show:

1994	Mara Wilson	Leno kept asking 7-year-old Wilson if she had a boyfriend despite saying she only had “friends that are boys”.
2000	Angelina Jolie	The actress lashed out at Leno after his “sick” jokes about Jolie’s close relationship with her brother.
2008	Martha Stewart	Leno made sexual advances on Stewart on the kitchen set where she was actually cooking. She seemed uncomfortable but kept the show going, ignoring the host’s antics.
2010	Sofia Vergara	Leno let his other guest, Gordon Ramsay get so touchy with Vergara. The host also asked the Modern Family star how much weight she gained over the holidays, mocked her accent, as well as her son Manolo’s name.
2011	Sofia Vergara (again, yes)	Vergara was defended by her co-guest Lady Gaga when Leno referred to the former’s relationship with his then-19-year-old son as “some cougar thing”. The singer said, “Jay! That’s so sick,” to which Vergara added, “I know, no respect.”

Jay Leno Is The Richest Late Night Host Despite His “Boring” And “Creepy” Reputation

Despite the backlash on his interview skills, Leno is still the richest late night talk show host with a net worth of $450 million, followed by Letterman who’s worth $400 million. Both comedians have a track record of “creepy” moments with female guests. The former Late Night star even “traumatized” Mariah Carey after focusing on her nervous breakdown during their interview. But he didn’t get the same “boring” attacks on Leno.

During his Tonight Show return in 2010 after Conan O’Brien was fired by NBC due to poor ratings, viewers called for a boycott, with critics picking on his comeback monologue. “Leno’s big return to the Tonight Show throne he abdicated for all of eight months was more of a letdown than we had even anticipated,” wrote New York Magazine‘s Mark Graham.

“Monday’s opening monologue, supposedly Leno’s strong suit, was tired, lame and unfunny. In other words, typical of the real Leno, rather than the Leno of public-relations imagination,” said Robert Bianco of USA Today.

Years later, Leno admitted he wasn’t thrilled about coming back to the show. He even told the network to ask O’Brien’s thoughts on the matter. But that clearly went south. He “just figured, let’s just play this out and see what happens” as it “all happened fairly quickly.” But hey, being “pretty loyal” to the network obviously paid off for him and his crew. I’d say he had the last laugh on this one.