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Jimmy Fallon speaking to audience
The Tonight Show/YouTube

5 Jimmy Fallon Moments in 2024 That Crossed the Line From Funny to Flat-Out Cringe

The Tonight Show Starring Jimmy Fallon is one of the strangest late-night TV programs ever. For the last decade, Fallon has hosted NBC’s most coveted spot, with varying results. The year of 2024 seemed to be an especially unfortunate year for Fallon. Here are the most cringe Jimmy Fallon moments of 2024.

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Interview with Chappell Roan

Chappell Roan in a 2024 interview with Jimmy Fallon on The Tonight Show

TV Talk Show Hosts have to speak with a lot of personalties. Due to the nature of the interview format, sometimes a host and guest just don’t click. However, Jimmy Fallon and Chappell Roan both appeared especially uncomfortable in their June 2024 interview on The Tonight Show. There was an awkward lack of chemistry, with Jimmy not seemingly knowing enough about the artist to ask her any interesting or insightful questions about her or her work.

However, the most infamous moment of the interview by far comes about four and a half minutes in, when Jimmy Fallon says he googled Chappell Roan earlier in the day “to see what pops up”. She immediately clocked him, asking if he knew who she was before. Jimmy slips up, says no, and facepalms as the audience roars with laughter. Chappell seemed visibly peeved by the moment, and it made Jimmy appear incredibly unprofessional and disinterested.

The Tonight Show’s Cringey YouTube Shorts and TikToks

Ariana Grande and Cynthia Ervo sing a song about Wicked on The Tonight Show Starring Jimmy Fallon

It’s no secret that legacy media is struggling more year after year as streaming becomes the dominant way to consume content. As a result, much of Late Night TV is consumed on streamers like Peacock or in YouTube videos, rather than being tuned into live. The Tonight Show Starring Jimmy Fallon has tried to adapt to the new media landscape by posting all sorts of content on YouTube Shorts and TikTok.

While these short from videos have had some viral appeal, most of them come off extremely cringe-worthy and dated. Perhaps the worst example, due to how much it dominated algorithms, is Ariana Grande and Cynthia Ervo performing a short song about the Wicked movie. Unfortunately the song is too simple, annoying, and not catchy enough to come off successfully. The obvious corporate attempt at a viral video to promote Wicked (which shares a parent company with NBC) fell flat, and seemed to annoy unwilling viewers more each time it was promoted to them via TikTok and YouTube Shorts Algorithms.

The Tonight Show with Jimmy Fallon has made other attempts at making funny, viral moments happen with other celebrities, but many have fallen flat. Take for example the Cody Rhodes, Take Me Home video. It starts with Jimmy Fallon doing a parody of John Denver’s “Take Me Home, Country Roads” with the aforementioned WWE Wrestler’s name, before he smashes Jimmy’s guitar and does a beat down on a doll of the TV Host. The joke feels like something befitting a decade old Vine, yet the dated, corny joke stretches to 30 seconds.

Macy’s Thanksgiving Day Parade

Jimmy Fallon with Al Roker for the Today Show on NBC Thanksgiving Day Parade

The Macy’s Thanksgiving Day Parade is a longtime holiday tradition. Every Thanksgiving in New York City, the massive parade draws in huge crowds in person and a massive TV audience on NBC. Due to the nature of the event, The Macy’s Thanksgiving Day Parade is aired live, unlike Jimmy Fallon’s show. As a result, there’s far more room for things to go awry then there is on The Tonight Show Starring Jimmy Fallon, which is pre-recorded.

Jimmy Fallon joined the Thanksgiving Day Parade to promote his Holiday Seasoning Spectacular Christmas Special and accompanying album. In his moment, NBC shifted all the broadcast’s attention to Fallon, who seemed to be struggling to keep up. Between almost missing his float, wearing sunglasses on a cloudy morning (causing speculation about his state of being), and struggling to respond to interview questions, Fallon had a rough go of it during the Thanksgiving Day Parade. While his blunders can mostly be chalked up to the speed and volume of the parade, his apparent struggle through the event made for an awkward appearance that clearly wasn’t going his way.

Jimmy Fallon’s Holiday Seasoning Spectacular

Jimmy Fallon Holiday Special.

The aforementioned Jimmy Fallon Holiday special ended up being a little less spectacular than its name would suggest. Jimmy Fallon’s Holiday Seasoning Spectacular features several musicians and celebrities, including longtime Fallon friends like Justin Timberlake. However, even their bromance couldn’t save this awkward special.

The biggest issue with Jimmy Fallon’s Holiday Seasoning Spectacular is that even though it features lots of A-List celebrities and talented musicians, Fallon won’t let the spotlight leave him long enough for any of them to shine. Not a single artist featured has a solo song performance, and Jimmy Fallon’s unremarkable singing abilities and corny song topics made for an underwhelming show. NBC clearly understands the appeal of silly, comedy Christmas songs. Saturday Night Live has some classics in the sub-genre, including with Justin Timberlake who appeared at the Holiday Seasoning Spectacular. However, leaving the hosting and singing up to an SNL alumni whose perhaps most known for breaking character and laughing his way through most sketches proved to be a poor choice.

Jimmy Fallon and the Costco Guys

Jimmy Fallon with A.J. Big Justice and The Rizzler (The Costco Guys) on The Tonight Show Starring Jimmy Fallon

Father/son duo A.J. & Big Justice have made waves all over social media in 2024. The pair became popular for their short form reviews of Costco food, where they give good products a “Boom” and bad products a “Doom”. They’ve had a massive year, expanding the Costco Guys brand to include several other members such as The Rizzler, and appearing as in-ring talent in AEW Wrestling.

The Costco Guys’ massive, wholesome social media appeal inevitably lead them to The Tonight Show Starring Jimmy Fallon. While Fallon is usually criticized for overselling his interest in guests and laughing hysterically at relatively normal anecdotes, he seemingly couldn’t hide his disdain for the group. Throughout the interview with A.J. & Big Justice and The Rizzler, Fallon appeared visibly vexed, and several times frustratingly tried to move the segment along, or cutoff their ionic celebratory “Big Booms”. Fallon was ripped to shreds for the lackluster interview on social media, with a Body Language Analysis of the interview receiving over a million views on YouTube. By far and away, this blunder with the Costco Guys seems like it’s the most talked about moment that had folks cringing at Jimmy Fallon in 2024.


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Author
Image of Haiden Lovely
Haiden Lovely
Contributing Writer
Haiden is a Contributor at The Escapist who has been writing about games since 2023. They love a good live-service shooter, especially Call of Duty: Zombies and have a complicated relationship with Madden Ultimate Team. Haiden brings experience in writing about games and entertainment, video production and podcast hosting from Strangely Awesome Games.