Top 10 Times Guests Called Out Jimmy Fallon

Whether you’re meeting an old friend for lunch or welcoming them to your talk show, there are some things you just habitually say to sound polite (even if it’s a bald-faced lie). “You look great” is one example. Hearing Fallon compliment his appearance, Ricky Gervais assumes that the host is either being sarcastic or phony. Gervais goes on to rant about how he looks even worse than he did the last time he was on the show. Painting a graphic picture, Gervais says that he’s heavy above the belt, but lacking below the waste. The comedian can’t fathom the idea of Fallon honestly thinking that he “looks great.” Even when Gervais is making fun of himself, he manages to rope someone else into the self-deprecation.

RuPaul is “a drag queen,” but that description hardly does him justice. Fallon learned this the hard way when the “Drag Race” host dropped by his desk. The conversation gets off on a lighthearted note with Fallon sharing the latest issue of Vanity Fair, noting that RuPaul was the first drag queen to make the cover. Suddenly, a straight-faced Fallon goes white as a ghost when RuPaul interjects over this label. RuPaul corrects Fallon, saying that he’s “The Queen of Drag.” The interview is all laughs from there, but the clip of RuPaul messing with Fallon went viral, honing in on the host’s stunned expression. Fallon even brought the moment up on a subsequent show, saying that he thought he had been canceled.

For a segment called #FallSongs, Fallon enlisted musical guest Shawn Mendes. #FailSongs might’ve been a more accurate title, however. Singing a parody of Simon & Garfunkel’s “The Sound of Silence,” Mendes’ timing isn’t quite in sync with the band. Mendes playfully pins the blame on Fallon, insisting that his cue was off. As Fallon attempts to make sense of the mix-up, Mendes suggests that the host simply had a senior moment. While the next few songs go smoothly, Mendes continues to bring up how much younger he is than Fallon, at one point comparing the host to his grandfather. Fallon ultimately takes the teasing in stride, but things get personal during another appearance when Mendes implies that Justin Timberlake likes him better.

Fallon is far from the first comedian to take a shot at politician Chris Christie’s weight. Yet, only a select few have made a body image joke straight to the former governor’s face. As Christie reflects about getting ice cream with Mitt Romney and Marco Rubio, Fallon interjects to say how excited he must’ve been to indulge his sweet tooth. Christie doesn’t hesitate to bid the audience farewell and walk off mid-interview. Fallon convinces Christie to come back, but the host isn’t getting off with a slap on the wrist. Christie says that if he ever steps away from politics, Fallon will have to bring some new writers on board to come up with fresher material, as opposed to the “garbage” jokes about him.

What do Fallon and Ellen DeGeneres have in common? Well, a few things that we don’t have time to unpack, but both can identify with feeling the wrath of Dakota Johnson’s sharp tongue. Apparently, Johnson has been sprayed by a skunk more times than she’s played Anastasia Steele. Johnson attempts to recount her dog’s skunk encounter, but Fallon keeps interrupting with questions. He’s especially focused on the incident’s location even though Johnson repeatedly says Big Sur. Struggling to get in a word, Johnson finally reminds Fallon that the idea of a talk show is to let the guest talk as well. Fallon is caught off guard, much like someone who spots a skunk in the woods. Johnson really needs to host her own talk show.

Fallon and John Oliver are both late-night hosts, but their styles couldn’t be more different. One generally avoids difficult subjects while the other pulls no punches. This was reflected during a game of “Hey Robot” where Oliver brought up the working conditions that Amazon employees face. As Oliver calls out Amazon, Fallon gets stuck in the middle while attempting to keep Alexa in her bottle. It’s not the only time that Oliver put Fallon in a sticky situation. In another appearance, Fallon complimented the title of Oliver’s “Last Week Tonight.” Oliver found it funny that Fallon singled out the title, as if there was nothing of greater value. Fallon proceeded to praise the show itself, but Oliver couldn’t resist backing him into an awkward corner.

Nicole and Tom. Nicole and Keith. Nicole and Jimmy? The latter never materialized, but in an alternate universe, Fallon could’ve been Mr. Kidman. In a 2015 appearance, Kidman and Fallon had slightly different accounts of their last encounter, although both agreed it was cringe. Through a mutual friend, Kidman visited Fallon’s apartment years earlier. Fallon seemingly thought it was a casual meeting. Kidman revealed on the show that she had a thing for Fallon, thinking that it was a date. So, you can imagine Kidman’s disappointment when the underdressed Fallon spent most of the night playing video games rather than talking to her. It wasn’t until Kidman called him out that Fallon realized that he blew his shot. Both are married now anyway.

Of all the late-night talk show hosts, Fallon was arguably the most lenient toward Trump during his first presidential campaign. That might be why Trump let him get up close and personal in September 2016. The interview culminated in the infamous hair tousle, which many saw as a way of normalizing Trump’s behavior. While Fallon says that wasn’t his intent, his ratings took a dive regardless. Fallon expressed regret in 2018, prompting the then-president to fire back on the social media platform then-known as Twitter. Trump claimed that his presence resulted in “monster ratings,” telling Jimmy to “be a man.” No longer tiptoeing around Trump, Fallon responded, “In honor of the President’s tweet I’ll be making a donation to RAICES in his name.”

Having seen a segment where Fallon pokes fun at his album cover, Blake Shelton wastes no time calling out the elephant in the room. As Fallon continues to ponder about the cover’s deeper meaning, Shelton attempts to contain his thoughts with an uncomfortable smile. This only intensifies as Fallon imitates a young Shelton and his family. After about two minutes, Shelton asks Fallon to get on with the interview already. Fallon lays off the cover, but he finds other subjects to argue with Shelton over, such as his new restaurant and “The Voice.” All the while, Shelton takes shots at Fallon’s interviewing skills. Fallon returns the favor with a performance of “I’ll Name the Dogs.” Maybe that’s why Shelton didn’t invite him to his wedding.

Whenever the Martins are on “The Tonight Show,” they never miss an opportunity to roast the host. However, one particular moment stands out four years after it initially aired. Short said that of all the late-night personalities, Fallon pretends to care the most. Short proceeds to praise Fallon’s “phoniness” before Martin takes a few more jabs at his clean image. At the time, it seemed like the two were just having a little fun at Jimmy’s expense. Looking back now, though, one can’t help but wonder if they were being brutally honest. Admittedly, it’s probably the former, but you can nonetheless see why this clip regained relevance in September 2023 when Fallon’s “Tonight Show” was met with toxic workplace allegations.

So… how about that Jimmy Fallon, eh? Any hot takes? Let us know your thoughts in the comments.