Here Are 8 Times Jimmy Fallon Had Hilariously Awkward Moments with His Guests

Jimmy Fallon's Interview "Fails"

He's a natural when it comes to making people laugh. The comedian and TV host has had many moments where he entertained his guests to the fullest. Be it celebrities, singers, or politicians, around Fallon, there are no dull moments. The 49-year-old once dared to mess up ex-president Donald Trump’s hair on live TV. In an interview with The New York Times, the host clarified, "I didn't do it to humanize him." However, there are also moments of authentic awkwardness.

1. Dakota Johnson called out Jimmy

In an interview from 2018, Dakota Johnson had a brief tussle with the host of The Tonight Show Starring Jimmy Fallon. Apparently, he asked the Persuasion star about the skunk attack and why she sliced tomatoes and placed them on top of her dog. The actress was laughing and talking simultaneously. So, Fallon kept talking which irked Johnson, "Aren't you supposed to let people talk on this show?" He responded, "If they know what they are talking about then yes."

2. Fat joke on Chris Christie

Chris Christie is a well-rounded man, yes. But Fallon again made fun of the politician's size in an interview from 2015, roasting the former governor of New Jersey for his bulky body. The 61-year-old confronted the comedian for his monologue fat jokes while the two fought over a tub of Ben & Jerry's ice cream. Christie called out, "If I ever leave public life, you're gonna have to hire two writers just to replace the garbage you say about me." 

3. Problem with Joaquin Phoenix's moniker

During a 2019 interview with the Gladiator star Joaquin Phoenix, Fallon visibly struggled to keep going since the actor gave him a hard time. Renowned for his habit of talking more and listening less, Phoenix's responses were like curveballs that the host could not dodge. At one point, Fallon told his guest, "I feel like your [name] is too long for me." The actor hit back, "You can handle it. You do a monologue every night," making the audience laugh.

4. Steve Martin and Martin Short roasting Jimmy

It's safe to say legends Steve Martin and Martin Shorts are among the most hilarious actors in Hollywood. So, when joined Fallon on his late-night show, the threesome had a blast roasting each other, including the host. Shorts went first and quipped, "This is the greatest show on television because there's no host in late night that pretends to care the way you do." This was followed by Steve, "I think for somebody who does meth, your teeth look great."

5. Jimmy "fake praising" John Oliver's show

When two contemporaries from the late-night show world come face-to-face, sparks are bound to fly. In a 2018 interview with John Oliver, Fallon had a few awkward moments with the fellow comedian. In one of the segments, the 49-year-old genuinely tried to compliment him, "Last Week Tonight, which I still think is the best title of any show ever." However, it seemed Oliver was in his element, "The best title? That sound like you damning me with fake praise, Jimmy."

6. Shawn Mendes kept calling Jimmy "old"

Nobody feels comfortable when someone calls you "old," and keeps saying that over and over. That's how Fallon's interview with singer Shawn Mendes turned out. The Stitches singer tried to clarify, "I told you I am just not as old as you." The audience burst out laughing and whoa'd. The host responded, "Son, don't talk back to your father like that." Mendes insisted, "You don't look old, you are fine. You are just old." The host failed to clap back.

7. Lost cool at Charles Barkley

Charades may look like an easy game but it's not. Fallon realized it on his show when the late-night host played it alongside Ewan McGregor, Charles Barkley, and Jeff Tweedy back in 2014. During the segment, Fallon lost his cool at Barkley for being unable to guess the cues he was giving him and shouted, "You have played charades before have you not?" This was followed by more moments of screaming like, "Four words" and "What the hell was that?"

8. Jimmy gets Rami's number wrong

The late-night host spoke highly of his guest Rami Malek and his performances. During one of the segments, Fallon gushed over the actor and said, "If I had your email/phone number, I would have called you a gazillion times to say, 'You were unbelievable.'" To this, Malek corrected the host and said, "You have my e-mail and phone number." The 49-year-old got uncomfortable, "Ah, that's true but I decided not to call you," stuttering, "I Uh.. I Uh…" and laughed.