The Most Uncomfortable Fallon Interviews Ever

Jimmy Fallon was the new kid on the late-night block when he took over The Tonight Show in 2014. The long-running series has remained a staple in television since 1954 and has seen a variety of hosts throughout the years — including TV icon Johnny Carson, who dominated the show between 1962 and 1992. While the Saturday Night Live alum had a lot to live up to, he's come across as a total darling between his pleasant jokes and a jovial nature that's equivalent to an excited puppy. "I'm a people pleaser," he told The New York Times in 2017. "If there's one bad thing on Twitter about me, it will make me upset." However, you can't always please everyone ... especially between Fallon's large fan base and harsh critics. The New Yorker, for example, once touched on the titular host's demeanor, writing, "Fallon's an enthusiast, which sounds good, until you see him spray the same gush on everything." Ouch.

It's not just viewers who've criticized Fallon — some of his celeb guests have made him squirm, as well. While some have enjoyed making the comedian appear visibly uncomfortable, others have gone straight for the jugular, calling him out for allegedly being fake. That said, it all makes for TV gold, so let's take a look at some of the most uncomfortable Fallon interviews ever.

Cardi B is just as well known for her over-the-top demeanor and trademark catchphrases as she is for her catchy beats and lyrical flow. So, you'd think that Jimmy Fallon would have done some research on what to expect from the Bronx native ahead of her 2017 appearance on The Tonight Show. Equipped with all her signature sounds and quick-witted jokes, the "Bodak Yellow" rapper was indeed in full Cardi B mode. The problem? It looked like Fallon didn't quite know how to handle her unique energy, which made for an interview that left some fans cringing.

At the start of the segment, the artist had already begun with her noises, which Fallon seemingly attempted to ignore at first. After he asked Cardi B about her NYC upbringing, she responded with her signature "Eeeoooow" sound, leaving Fallon to simply sit in silence before taking a sip of water. As the interview went on, he appeared to fall into more of a hilarious groove with the rapper, but the whole thing came off as pretty uncomfortable and, as one Twitter user put it, "So entertaining for Cardi, but awkward for Jimmy."

Saturday Night Live star Pete Davidson made his Tonight Show debut in 2018 to chat about his short-lived engagement to then-fiancée Ariana Grande. The interview started off easily enough, with the comedian gushing about the relationship. However, when Fallon suggested that the late-night show itself would be a perfect place for the Hollywood duo to get married, Davidson shot back with, "Why do people care? It's very weird. It's weird 'cause like the president's like trying to pardon himself and he's like f**king a porn star." This, of course, was in reference to Donald Trump's alleged affair with Stormy Daniels.

The audience responded to the candid remark with some scattered laughs, while Fallon himself laughed it off but looked a bit uncomfortable. Undeterred, Davidson continued to throw out profanities throughout the interview. Finally, the host told the funnyman that he can't say those words on live television and jokingly "fired" him from the show. "No it's fine, I'll go on Seth [Meyers' show], I don't give a s**t ... I actually have Seth's number, I don't have your number," Davidson quipped. To which Fallon quickly retorted, "And you're never gonna get it either." The entire exchange was met with shocked howls from the in-studio crowd.

Luckily, Davidson and Fallon's awkwardness together made for such comedic gold that NBC appeared to excuse the former's verbal hiccups and gave him the green light to return to the show multiple times since.

Jimmy Fallon's 2016 interview with Nicole Kidman didn't really stand a chance. Things turned awkward when the comedian began laughing nervously right off the bat. In response, the actress playfully rolled her eyes but fidgeted in her seat, semi-jokingly saying, "I so didn't wanna come back." While this caused Fallon to hysterically crack up, Kidman pressed on in an attempt to keep the interview on track. "I'm in a new movie, Lion, so that's why I'm here," she told the host, who appeared to have plans of his own.

Fallon began rehashing the starlet's previous appearance on his show the year before ... which had been mega uncomfortable in and of itself. At the time, it was revealed that the duo once went out on a date together years before. The problem? The SNL alum totally blew his chance with the Hollywood beauty. After admitting that she'd had a crush on Fallon at the time, Kidman explained that she'd asked a mutual friend to set them up. However, when she went over to the comedian's crib, he "wouldn't talk" to her and ended up playing video games for an hour before she gave up and left. With a laugh, Kidman told the embarrassed host, "It was bad!" For his part, Fallon claimed he didn't realize it was an actual date at the time. But still, talk about cringe.

While he's famously engaging and animated with his guests, Fallon appeared to tone things down a bit during his interview with late-night rival John Oliver in 2018. The Last Week Tonight host played up this dynamic after Fallon asked about his role of Zazu in the live-action remake of The Lion King. "I'm a movie star," Oliver jokingly said, adding, "You respect me, Jimmy, I'm a movie star now! ... Some s**t's about to change around here." The British comic went on to discuss his experience singing the Disney classic, "I Just Can't Wait to be King," for the part. Well aware that he's no professional crooner, Oliver brushed off the production's note that he sang "great" as "Hollywood bulls**t" — an ironic remark, considering Fallon's next move.

The titular host turned his attention to Oliver's small-screen endeavor: His award-winning HBO show. However, Fallon started off by giving his guest a pretty weak compliment, saying it's "the best title of any show ever." Without skipping a beat, Oliver gave him a deadpan blink and quipped, "The best title? Wow, that sounds like damning me with fake praise, Jimmy. 'I really love the title, it goes downhill once that's finished.'" Not to be taken too seriously, both began to crack up, as Oliver admitted, "It's so dumb. It makes no sense."

It's hard to imagine annoying Blake Shelton, the laid-back country crooner and Gwen Stefani's long-term beau ... which made it all the more surprising to see him nearly lose his cool when he appeared on The Tonight Show in 2017. Fallon kicked things off by incessantly heckling his guest over the cover for his eleventh studio album, Texoma Shore, with what began as light-hearted humor.

"What are you thinking here? About memories of where you are?" the host asked Shelton, who tried to keep things amicable as the audience laughed. "Right now, I'm thinking about wishing I was there," the singer jokingly retorted. However, the comedian didn't seem to take the slight hint to move on and began a bit about Shelton's upbringing by imitating Southern accents and stereotypes. The Voice judge looked semi-annoyed as the so-called joke went on, and didn't laugh at Fallon's impromptu sketch. However, after a couple more minutes of banter, Shelton appeared to have enough and finally said to Fallon, "Will you interview me for God's sakes?" As the host began the actual interview, the musician semi-jokingly muttered, "Thank God." Yikes!

Notorious for his style of self-deprecating cringe humor, Ricky Gervais admittedly has no filter. In a 2019 interview with The New York Times Magazine, the comedian even explained this notion himself, saying, "I joke about AIDS, famine, cancer, the Holocaust ... That's one of the things of comedy: laughing at the wrong thing because you know what the right thing is."

With this self-professed view of what's right and wrong — particularly through the lens of comedy —it should come to no surprise that the British entertainer immediately latched on to Fallon's penchant for giving out seemingly fake compliments during his 2017 appearance on the late-night show. The host began by telling Gervais that he "looks great," which was enough to send his guest into a long-winded rant about his appearance. "I look great? Is that sarcasm?" the stand-up comic rhetorically asked. "You see, this is the thing with you, the talk show, 'Oh you look great.' Even though, look at me! Of course I don't look great!" The creator of the British version of The Office finished his hilarious, four-and-a-half minute tirade about weight gain with a string of profanity, causing Fallon to look off-camera and playfully cut his guest off in an attempt to continue on with the interview itself.

Just months before five women would accuse him of sexual misconduct in a shocking exposé for The New York Times in November 2017, comedian Louis C.K. was making his rounds on the talk-show circuit to promote his Netflix stand-up special. He and Jimmy Fallon seemingly got along just fine at the top of his appearance on The Tonight Show that March — that is, until the host appeared to forget how to use his brain.

C.K. began the interview by telling Fallon just how much he loves napping. Midway through his rave about the activity, the late-night host suddenly asked, "You like it better than sleep?" ... which was all it took to leave the Louie alum utterly perplexed. Gracing us all with the most epic side-eye ever, C.K. jokingly remarked, "You really ... That's stupid you just said that. That was a dumb thing to say. That's such a dumb thing to say." The comic went on to further rip into Fallon, offering multiple analogies showcasing just why he felt the question was so absurd. For his part, the former SNL star tried to save the entire situation through rationale, before C.K. finally dropped the banter with a chuckle, asking him, "Can you just get past this part?"

Comic legends Steve Martin and Martin Short aren't just longtime showbiz besties, they're also utterly hilarious together. Ever since starring alongside Chevy Chase in 1986's ¡Three Amigos!, these two have been known for their fabulous banter. However, when they appeared together on The Tonight Show in 2019, they used the opportunity to rip into host Jimmy Fallon, turning the interview into more of a Comedy Central Roast than a casual late-night appearance with rapid-fire jokes aimed at the talk show host's alleged fakeness.

"This is the greatest show on television because there is no host in late night that pretends to care the way you do," Short began. As Fallon laughed along and thanked his guest, Short kept going with, "I mean, no one captures phoniness the way you do, it's a gift." Without skipping a beat, Martin jumped in on the so-called fun, saying, "When I'm home, you know, watching the show — which is rare ... I'm thinking, 'Wow for somebody who does meth, your teeth look great!'" Finishing Fallon off, Short declared, "You prove that tall, handsome white men can make it in show business." Ouch! While Fallon initially laughed off all of their jabs, he was noticeably quieter near the end of the impromptu roast, before recovering to move on with the interview. But, perhaps the iconic comedy duo struck a nerve?

Singer-songwriter Shawn Mendes had not one, but two pretty uncomfortable appearances on The Tonight Show Starring Jimmy Fallon. The hitmaker first went on the show in 2016 to help the titular host out with a #FallSongs bit. However, as Mendes finished the second song, he called Fallon out for giving him a late cue to begin singing, before making a number of pointed jokes about the comedian's age. While the audience laughed at the first quip, this response subsided as the youngster continued to hit Fallon with similar verbal blows. "You sound like my grandfather," Mendes later told Fallon ... which was awkwardly met with crickets from both the talk show host and his audience of devotees. Cringe.

Miraculously, Mendes returned to the show two years later, and opened up to Fallon about performing with Justin Timberlake at the 2018 iHeartRadio Music Festival. The comic, who shares a very public BFF bromance with the pop star, jokingly heckled his guest over who Timberlake likes more after Mendes gushed that the two are "pretty good friends now." However, as the banter continued throughout the interview, things progressively got a bit more awkward. Fallon's final go-to move to squash the playful beef? That infamous over-the-top laugh.

Jimmy Fallon's 2016 interview with then-presidential candidate Donald Trump left countless Americans disappointed and enraged. The issue? Well, he was simply being Jimmy Fallon. The Tonight Show host kept things light-hearted and avoided pushing any political buttons — something his peers, such as Jimmy Kimmel and Stephen Colbert, noticeably fed off of back then and ever since. The late-night host finished off his interview with a notorious pièce de résistance — he playfully messed up Trump's hair. 

Viewed by some as normalizing the soon-to-be president's divisive rhetoric, the move was widely criticized and eventually cost Fallon 21 percent of his audience by the following year, according to The New York Times. Fans were furious with the host, and he later admitted on The Hollywood Reporter's Awards Chatter podcast that the days following the incident were a "down time" for him. "I'm sorry," he said during the emotional 2018 interview. "I don't want to make anyone angry — I never do and I never will." While Fallon expressed remorse, Trump was busy being, well, Trump, and took to Twitter to share his own thoughts on the comedian's podcast interview. Accusing the late-night host of "whimpering," the President of the United States finished things off with, "Be a man Jimmy!" Good grief.

By 2019, The Tonight Show had bounced back with top ratings in the late-night sphere, but it seems as though Fallon's image may have, at least to some, remained somewhat tainted.