Whether you love it or hate it, The Tonight Show has a rich television legacy that stretches back for decades. The show remains very popular just as much for the wild celebrity interviews as the “zany” antics of Jimmy Fallon.
However, sometimes the show was memorable for all the wrong reasons. This is especially true when those celebrity interviews went completely off the chain!
Just how weird did things get? Keep reading to discover the most insanely awkward Tonight Show interviews!
Donald Trump
Jimmy Fallon’s whole thing is being affable to almost any guest, even when they are very controversial. But that really blew up in his face when he interviewed Donald Trump back in 2016.
This was when Trump was on the campaign trail for president and hoping to bolster his image. Toward the end of the interview, Fallon playfully mussed Trump’s hair to illustrate that it was real and not a hairpiece.
For many of Fallon’s fans, Trump was already deeply unpopular, so the late-night host ended up losing over 20% of his viewers. He ended up apologizing, but as Trump became president and performed one controversial act after another, many of Fallon’s former fans never forgave him for trying to normalize Donald Trump in this way.
Blake Shelton
What happens when Jimmy Fallon stops being the affable guy and starts getting catty? When that happens, you get his bizarre 2017 interview with country music star Blake Shelton.
Apparently, having a southerner in the studio was just the motivation Fallon needed to start mocking Shelton’s accent and mocking generic southern stereotypes. Instead of laughing along, Shelton grimaced in annoyance most of the time, and he reacted by exclaiming “thank God” once Fallon moved past the jokes and onto the interview.
Louis CK
Back in 2017, Fallon interviewed the comedian Louis CK. This was before he was credibly accused of sexual misconduct by five different women. However, there were some serious signs during the interview that the comedian was not a nice guy.
For example, Louis CK casually mentioned how much he enjoyed napping. In an attempt to banter with the comedian, Fallon asked if he preferred napping to sleeping. Now, this wasn’t the best joke in the world, but Louis CK ended up doing more than not laughing. Instead, he tore into Fallon for a long time about how stupid both Fallon and his attempt at a joke were!
Heidi Klum
In 2003, Jay Leno interviewed Heidi Klum. Unlike most of the interviews on this list, it wasn’t awkward due to anybody’s personality. Instead, it was awkward due to Klum’s wardrobe and inevitable wardrobe malfunction!
As part of the world’s weirdest flex, Klum was walking around with a Victoria’s Secret bra worth $11 million. She opened up her coat and started flashing the goods. However, a diamond stud came loose on air, and she had to hold onto the coat to keep from anything, er, slipping out in front of millions of viewers. Soon, Jay Leno and guest Martin Short did the gentlemanly thing of holding their suit jackets in front of her so she could fix the issue without further exposure.
Bobcat Goldthwait
Do you remember watching Arsenio Hall? If so, don’t forget to do some stretches to ease that back pain!
In all seriousness, you may remember how disappointed fans were when the Arsenio Hall show was canceled. But nobody was more disappointed than comedian Bobcat Goldthwait. In his 1994 interview with Jay Leno, Goldthwait decided to make a statement about the matter by literally setting Leno’s chair on fire.
The fallout was both swift and inevitable. In addition to paying $3,000 to replace the chair, Goldthwait had to make a number of public service announcements regarding (what else?) fire safety.
Pete Davidson
Pete Davidson is a pretty funny guy, and so is Jimmy Fallon. But in an awkward 2018 interview, each actor’s humor ended up canceling each other out.
For example, things started out normally enough with Davidson talking about his then-relationship with Ariana Grande. After confirming they were now engaged, Fallon playfully suggested the two get married in the studio.
Suddenly, a defensive Davidson began questioning why people even cared about his relationships when Donald Trump allegedly had sex with a pornstar (or, as Davidson delicately put it, “f**king a porn star”) and then bribed her into silence. This was the beginning of the end, as Davidson kept launching into painfully unfunny profanity.
Eventually, Fallon told the comedian he couldn’t say these things on TV and jokingly “fired” Davidson from the show. Taking the jest seriously, Davidson responded “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.” To that, an icy Fallon quickly responded with “And you’re never gonna get it either.”
Cardi B
What happens when two completely different vibes collide? You get the awkwardness that was Fallon trying to interview Cardi B in 2017.
If you’re a Cardi B fan, you may know that she often makes signature noises in her different songs, including her famous “Eeeoooow” noise. Soon into the interview, she began dropping some of the noises she is known for…and it was enough to stun Fallon into silence!
No, really. Not knowing what to say or do, Fallon quietly sat there and sipped some water. They eventually got on the same page, but the first part of that interview is hilariously awkward.
Colin Farrell
In 2006, actor Colin Farrell sat down to an interview with Jay Leno. But it didn’t take too long for things to go off the rails.
That’s because Farrell had a stalker named Desiree Bradford and, unbeknownst to him, she was in the audience. During the interview, she made her way to the stage and threw a copy of her book onto Leno’s desk. The book in question? Colin Farrell: A Dark Twisted Puppy.
Farrell himself had to escort her to security. She wasn’t arrested, and Farrell went on to take out a restraining order against her.