10 Funniest Late Night Talk Show Moments, Ranked

Late-night talk shows have been a treasure trove of comedic gold for decades and have offered audiences some wildly unpredictable moments. Historically, talk show hosts like Johnny Carson set the stage for a format that evolved into today’s viral comedic phenomenon. With time, late-night TV entertainment became a fan favorite, and now, shows like The Tonight Show Starring Jimmy Fallon and The Late Show With Stephen Colbert are dominating. What sets late-night TV apart from traditional comedy skits is its ability to capture truly organic and unscripted moments — be it an awkward celebrity exchange or a fully orchestrated prank.

Recently, these moments have become pop culture milestones by gaining millions of views and shares across social media platforms like TikTok, YouTube, X, and beyond. More and more late-night shows are adapting by turning the standout moments from the show into viral clips. For instance, Jimmy Fallon’sLip Sync Battle Segments became so popular that they spawned their spin-off show. Not to forget that clip with Charlie Puth where he makes music with spoon and cup sounds on the go. And let’s not forget James Corden’sCarpool Karaoke, which broke viewing records by featuring artists like Adele and Paul McCartney. Here are 10 best over-the-top comedy bits from late-night talk shows that left viewers laughing long after the cameras.

10 Conan O’Brien’s Revenge on NBC

‘The Tonight Show’

Conan O’Brien’s exit from The Tonight Show in 2010 led to one of the most iconic moments of his late-night career. After NBC decided to move Jay Leno back into the 11:30 p.m. slot, O’Brien took his frustration to the screen. Instead of quietly stepping down, Conan used NBC’s money to create outlandish and absurd segments during his final weeks on air. These skits included purchasing a Bugatti Veyron and dressing it up as a mouse while playing The Rolling Stones ’ “Satisfaction” as background music.

Licensing the song reportedly cost NBC $500,000, allowing the comedian to humorously burn through their funds as payback for his ousting.

This period is now remembered as O’Brien’s comedic retaliation. Though NBC’s decision stirred public backlash, it also allowed the comedian to showcase his humorous revenge unforgettably. Despite the fallout, CNBC states that O’Brien negotiated a $45 million settlement, with a portion going to his staff. This solidified his legacy as a late-night hero and served as a testament to his quick wit.

9 James Corden Skydives

‘The Late Late Show with James Corden’

In one of the most adrenaline-pumping segments of The Late Late Show with James Corden, Tom Cruise convinced James Corden to go skydiving, despite the host’s obvious fear of heights. This moment aired in 2018 when the action star casually suggested the skydiving trip during a guest appearance on the show. Despite James Corden’s initial hesitation and genuine panic, Cruise reassured him with all his confidence.

The segment was not just about the skydive but the hilarious contrast between Corden’s visible terror and Cruise’s calm demeanor. The bit climaxes with Corden’s nervous but thrilling jump from 15,000 feet, an unforgettable moment for the host and the audience alike. Fans got to witness Cruise playfully tormenting Corden while reminding everyone that no stunt is too daunting for the Mission Impossible star. This comedic yet heart-racing event quickly became one of the most talked-about moments on late-night television. The YouTube clip of the show garnered over 60 million views and 1 million likes.

The Late Late Show with James Corden is not currently available for streaming in the US.

8 President Obama Interviewed By Zach Galifianakis

‘Between Two Ferns with Zach Galifianakis’

One of the funniest and most memorable moments in late-night talk show history was when Zach Galifianakis interviewed President Barack Obama on his interview show Between Two Ferns with Zach Galifianakis in March 2014. Known for its deadpan humor and awkward interactions, the show often features Zach Galifianakis delivering offbeat questions and absurd commentary. However, this episode took things to the next level by having a sitting president engage in humor.

During the interview, Obama showed remarkable comedic timing, playing along with Zach Galifianakis’ sarcastic questions.

At one point, when asked about running for a third term, Obama quipped that it would be like doing a third Hangover movie — a clear reference to the diminishing quality of the franchise’s sequels. Though the humor was lighthearted, the real intention behind Obama’s appearance was to promote the Affordable Care Act. This episode went viral, amassing millions of views, and is considered one of the greatest examples of how late-night funny platforms can effectively address serious topics.

WATCH ON PRIME

7 Dennis Quaid and The Hidden Camera Prank

‘The Ellen DeGeneres Show’

One of the funniest moments in late-night television came from Dennis Quaid’s unforgettable hidden camera prank on The Ellen DeGeneres Show in 2008. Ellen DeGeneres sent Quaid into a Starbucks with an earpiece, feeding him ridiculous commands. The unsuspecting baristas had no idea that Quaid was following her instructions, which led to a golden comedic moment. At her direction, Quaid loudly declared, “Dennis Quaid is here!” upon entering, confusing everyone in the coffee shop.

In another memorable prank, he was sent to a nail salon. Throughout the bit, Quaid spoke in the third person, confusing the salon staff. His bizarre behavior escalated as he bit into a tomato while receiving a manicure and asked the staff to teach him Vietnamese. These pranks were successful because of Quaid’s commitment to the show. His deadpan delivery of outrageous lines kept the salon workers completely confused. The moment remains a fan favorite and its clips are uploaded on TheEllenShow YouTube channel if someone wants to watch them.

The Ellen DeGeneres Show is not currently available for streaming in the US.

6 Nathan Fielder’s Staged Story

‘Jimmy Kimmel Live’

Nathan Fielder is famous for his deadpan jokes. His appearance on Jimmy Kimmel Live provided one of the most awkwardly hilarious moments in late-night television. While promoting Nathan For You, instead of the usual promotional talk, he captivated the audience by recounting an absurdly elaborate story involving an encounter with police. The story shared on the official YouTube channel involved a mix-up with the luggage at the airport, which led to him wearing a stranger’s oversized suit. The story also included a mysterious baggie with a “powdery substance” and a run-in with the police.

What made this moment even more special was the reveal in his show Nathan For You that the entire anecdote was meticulously staged. Fielder didn’t want to fabricate a story like many other celebrities do, so he spent months and over $350,000 to ensure every aspect of the story happened. Fielder orchestrated the entire sequence of events, from plane tickets to police bribes. The performance on Jimmy Kimmel Live was so convincing that nobody questioned its legitimacy at the time. This made the segment one of the funniest, and most thought-provoking moments on late-night TV.

5 Albert Brooks and His Stupid Pet Tricks

‘Late Night with David Letterman’

Albert Brooks’ telephonic appearance on Late Night with David Letterman in 1985 took the concept of Stupid Pet Tricks to a whole new level. Rob Reiner was the main guest on Late Night with David Letterman, but Albert Brooks managed to steal the spotlight over a phone call. Instead of bringing real pets onstage, Brooks humorously claimed to have pets perform over the phone and delivered his version of Stupid Pet Tricks — with no actual pets or visuals.

He described the actions of his dog over the phone, which offered a mental illustration of the imaginary pet tricks to the audience. Even though he wasn’t in the studio, his creative take on a familiar sketch was loved by everyone. By subverting the traditional format of Stupid Pet Tricks with his phone-in style, Brooks demonstrated how his clever humor could shine through in even the most unusual setups. The impulsive comedy and unpredictable performances from comedians made it one of the funniest and most memorable moments in late-night television.

Late Night with David Letterman is not currently available to stream in the US.

4 Adele and Carpool Karaoke

‘The Late Late Show with James Corden’

James Corden’s Carpool Karaoke featuring Adele is one of the segment’s standout moments. This fun-filled sketch originated from a Comic Relief bit with Corden and the late George Michael in the UK. Since bringing it to The Late Late Show, it has featured musical icons like Lady Gaga, Stevie Wonder, and even Madonna. However, Adele’s episode, which aired in January 2016, remains a fan favorite. As Corden drove around London, Adele sang her famous hits and even performed the Spice Girls’ “Wannabe” to showcase her sense of humor and nostalgia.

What made this episode a fan favorite, was Adele’s effortless transition between soulful performances and candid conversation. Her down-to-earth demeanor and humor endeared her to viewers, while her impressive vocal performances left fans in awe. It quickly became one of the most watched Carpool Karaoke episodes. The YouTube clip of the moment has gathered around 265 million views and over 3 million likes, solidifying itself as a fan favorite for its blend of humor, authenticity, and music.

3 Tom Holland Describes His Embarrassing Interaction With Madonna

‘The Graham Norton Show’

On The Graham Norton Show in 2018, Tom Holland hilariously recounted an awkward encounter with Madonna that still haunts him. The incident took place at a nightclub where Holland found himself introduced to the legendary singer. During the conversation, things took an uncomfortable turn when one of Holland’s friends blurted out to Madonna that he was an excellent dancer. Holland, caught off guard, explained that he wasn’t prepared for this.

Holland’s attempt to impress Madonna with his dance moves was far from successful. As he vividly described the embarrassment of his unimpressive performance in front of Madonna, the audience erupted in laughter. The Hollywood star further explained that he didn’t stick around and made a quick exit from the nightclub. His retelling of this encounter was both charming and relatable, exhibiting how even a Hollywood star can find himself in a hilariously cringe-worthy situation when meeting someone as iconic as Madonna.

WATCH ON FREEVEE

2 Kevin Hart And His Fear Of Animals

‘The Tonight Show Starring Jimmy Fallon’

One of the funniest moments on The Tonight Show Starring Jimmy Fallon occurred when Kevin Hart joined animal expert Robert Irwin — son of Steve Irwin — for an animal segment. Hart humorously made it clear that he wasn’t comfortable by saying “This is how black people die in a horror movie.” The moment that made the audience roar with laughter came when Irwin introduced a cuddly baby ostrich, which immediately sent Hart running off the stage in panic.

Things escalated even more when Irwin brought out snakes, leaving Hart steadfast in his refusal to interact. Even Fallon and the audience tried to coax him, but Hart humorously shut it down. The climax of this entertaining segment came when Hart was reluctantly convinced to let a falcon land on his arm while wearing a thick glove. His humor and fear meshed perfectly with the unpredictable nature of the show. Also, the sheer terror of the Hollywood star provided one of the funniest late-night moments of all time.

1 Rihanna Pranking Jimmy Kimmel

‘Jimmy Kimmel Live’

In a hilarious 2015 April Fool’s Day prank, pop star Rihanna teamed up with Jimmy Kimmel’s wife, Molly McNearny, to pull off an unforgettable late-night wake-up call on Jimmy Kimmel Live. The prank involved Rihanna sneaking into Kimmel’s home in the middle of the night with her crew, including a camera team, lights, and backup dancers. They stormed into his bedroom at 1 a.m., where Rihanna performed one of her hit songs at full volume, jumping on Kimmel’s bed and showering him with money.

Kimmel’s groggy and utterly confused reaction as he struggled to comprehend what was happening only made the prank funnier. Despite being known for playing pranks on his show, Kimmel was caught completely off guard. Rihanna’s elaborate set-up, complete with flashing lights and high-energy dancing, left him dazed. This moment set the bar for celebrity pranks on Jimmy Kimmel Live and remains one of the most iconic and hilarious stunts ever seen on the show.

Keep Reading: The 10 Best Modern Late Night TV Hosts, Ranked