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The Most Memorable And Iconic Moments In Late-Night Talk Show History

15 min read

Late-night talk shows, a tradition since the '50s, feature Hollywood stars in interviews, comedy sketches, and music performances. These shows have become an integral part of our entertainment culture, creating unforgettable moments that have stood the test of time.

Notable appearances, such as Bill Clinton playing the saxophone on Arsenio Hall's show or Tom Cruise jumping on Oprah's couch, still resonate in pop culture. These shows have kept us entertained for almost 70 years, with countless favorite moments to cherish.

Jimmy Kimmel vs. Matt Damon

The legendary Jimmy Kimmel and Matt Damon feud is a quintessential example of late-night talk show humor transcending the screen. This whimsical rivalry commenced when Kimmel jokingly claimed he had no time for Damon as a guest, an innocuous remark that spiraled into a beloved celebrity feud.

Kimmel retaliated by repeatedly attempting to replace Damon in various movie roles. The feud even involved Sarah Silverman, Kimmel's then-girlfriend, who created a viral sensation with her song "I'm F***ing Matt Damon." It escalated to the point of couples' counseling, all while audiences reveled in the ongoing, hilarious antagonism. 

Madonna Drops the F-Bomb

Madonna's unforgettable appearance on the Late Show with David Letterman in 1994 sent shockwaves through late-night television. The iconic pop superstar pushed the boundaries of censorship by casually dropping the F-bomb an astonishing 14 times, earning the dubious honor of hosting the most-censored late-night interview to date.

The interview was riddled with innuendos and risqué jokes, and Madonna cheekily quipped about being there because there was no Knicks game to attend. The nature of her relationship with Letterman, whether it was genuine or an act, remains a mystery, adding an extra layer of intrigue to this wild and controversial late-night TV moment that still resonates with audiences today.

Ariana Grande and James Corden Go to Starbucks

Starbucks patrons received an unexpected jolt of excitement when pop sensation Ariana Grande and the ever-entertaining James Corden embarked on an impromptu Carpool Karaoke session. Ariana Grande, known for her vocal prowess and sense of humor, introduced herself in typical celebrity fashion but took it up a notch by humorously insisting that she must be carried.

The shock and amusement among the Starbucks workers and customers were palpable as they quickly fumbled for their smartphones, eager to capture the star-studded moment for posterity. It was a delightful and surprising intersection of everyday life with celebrity charm, leaving everyone with an unforgettable coffee shop story to share.

Nicole Kidman Could’ve Dated Jimmy Fallon

Celebrities, just like us, have their fair share of amusing dating anecdotes. Nicole Kidman and Jimmy Fallon, for instance, shared their charmingly mismatched recollections of their first meeting on The Tonight Show. Kidman confessed that she had a significant crush on Fallon, but he remained utterly oblivious to her interest.

Fallon, during the interview, displayed genuine embarrassment for not realizing Kidman's intentions at the time, providing a hilarious and endearing twist to their encounter. This candid exchange between the two stars showcased the relatable and often comical aspects of dating that resonate with people from all walks of life.

Drew Barrymore Gives David Letterman a Show

Drew Barrymore, beloved for her role in "E.T.," delivered a jaw-dropping surprise during her appearance on David Letterman's show. Referencing her recent visit to a club, she took spontaneity to a new level by suddenly jumping on the host's desk, playfully lifting her shirt to reveal her bare chest.

Courtney Love, in a later imitation, attempted to recapture the shock value of Barrymore's bold move, but it couldn't quite match the original's impact. Barrymore's fearless, unscripted moment remains etched in the annals of late-night TV history.

Tom Hanks Whale Watching Prank

Tom Hanks, renowned for his charm and affability, made a dapper appearance on a late-night show where he regaled the audience with his recent whale-watching adventure. As he excitedly described the awe-inspiring moment when a massive whale leaped out of the water, the unexpected happened – the whale's powerful splash drenched him from head to toe, leaving the audience in stitches.

The host managed to stay dry, but Hanks, ever the good sport, took the mishap in stride. With a grin, he even added water to his face for comedic effect, turning an unplanned soaking into a moment of unforgettable late-night hilarity.

Harrison Ford vs. Chewbacca

During a memorable late-night interview, Chewbacca, the iconic Wookiee from Star Wars, displayed an uncharacteristic grumpiness when faced with a barrage of questions about the legendary franchise. Jimmy Kimmel, known for his playful antics, decided to test Chewbacca's patience further by surprising him with a group of fans dressed as various Star Wars characters.

However, the unexpected drama took a sharp turn when Harrison Ford, the man behind Han Solo, expressed his irritation at Chewbacca's antics, causing a stir around Ford's wife. The tension escalated to the point where Ford asked Kimmel to choose sides, ultimately leading to an abrupt and dramatic exit from the show, leaving the audience and host in shock.

Conan O’Brien Gets Back at NBC for Taking “The Tonight Show”

The late-night television saga that unfolded when Jay Leno retired from The Tonight Show and handed it over to Conan O'Brien, only to return and reclaim the show, was nothing short of a Hollywood spectacle. The ensuing shake-up left Conan understandably disgruntled. In a bold act of rebellion, he spent a whopping $1.5 million on a Bugatti Veyron.

As the ultimate act of televised revenge, Conan played the expensive Rolling Stones song "Satisfaction" on air, symbolizing his dissatisfaction with the turn of events and leaving an indelible mark on late-night TV lore.

Joaquin Phoenix Bombs While in Character for “I’m Still Here”

In a memorable late-night interview, David Letterman unwittingly stumbled into a theatrical ruse when he pointed out Joaquin Phoenix's disheveled appearance, not realizing it was part of a stunt for a film project. The exchange took an uncomfortable turn when Letterman criticized Phoenix for chewing gum and delivered a series of sarcastic remarks that left both the host and guest at odds.

However, in the aftermath, Joaquin Phoenix issued a heartfelt apology, clarifying the context of his appearance and explaining the misunderstanding. This gesture of reconciliation marked the end of the rift and served as a testament to the unpredictability and genuine nature of late-night television moments.

Adele’s Carpool Karaoke

James Corden's Carpool Karaoke has become a beloved staple of late-night television, with a parade of superstar guests, including Mariah Carey, Elton John, Lady Gaga, Sia, and Justin Bieber. Among these stellar moments, it was Adele's appearance that truly captured our hearts.

The magic didn't stop there; the icing on the cake was Adele's unexpected and flawless freestyle rap at the end. Her lyrical improvisation left both Corden and the audience in sheer awe, demonstrating once again that Carpool Karaoke can produce some of the most extraordinary and memorable late-night moments in the history of the show.

Marlon Brando Kisses Larry King

Marlon Brando, the enigmatic Hollywood legend known for his reluctance to give interviews, surprised the world with a rare and unexpected conversation with Larry King at his home. This unique encounter took a quirky turn when the two, in an unusual display of camaraderie, broke into song and even shared a light-hearted kiss while discussing Brando's book.

The interview concluded with a simple yet somewhat awkward handshake, a fittingly unconventional ending to a conversation that had provided a rare glimpse into the reclusive actor's life and sense of humor. It remains a memorable and cherished footnote in the history of celebrity interviews.

“Cheers” Cast Gets Tipsy After the Show’s Finale

In a memorable television moment, the cast of the hit show "Cheers," including Ted Danson and Kelsey Grammer, reunited for an interview with Jay Leno in 1993, broadcast live from the iconic Cheers bar in Boston. However, what made this reunion truly unforgettable was the cast's apparent inebriation.

At the time, it was indeed uncommon to witness celebrities in a somewhat tipsy state on a late-night show, making this jovial and unscripted reunion a classic and endearing display of camaraderie, which added another layer of nostalgia to the beloved show's farewell.

Jerry Lawler Slaps Andy Kaufman

The wrestling world and entertainment industry collided in a bewildering spectacle when wrestler Jerry Lawler and actor/wrestler Andy Kaufman took their infamous rivalry to a late-night show. What ensued was a heated exchange filled with verbal jabs and even coffee-throwing.

The audience was left in a state of confusion, unsure whether this intense encounter was real or a staged performance. But one thing was certain: the unforgettable clash between Lawler and Kaufman transcended the boundaries of professional wrestling and late-night entertainment, leaving an indelible mark on the annals of pop culture.

Jimmy Kimmel Impersonates Jay Leno

The late-night television landscape witnessed a seismic shift when NBC surprised everyone by replacing Jay Leno with Conan O'Brien on The Tonight Show. However, the unexpected drama continued when Leno made a comeback, cutting short O'Brien's relatively brief stint as the host.

Notably, Jimmy Kimmel joined the fray, donning a hilarious impersonation of Leno in a comical episode. Although his specific reasons for being upset remained somewhat unclear, Kimmel's parody added another layer of humor to the late-night showdown, illustrating the complex dynamics and rivalries within the industry. 

Lip Sync Battle with Emma Stone

While the Lip Sync Battle stage has hosted numerous electrifying performances, Emma Stone's appearance remains an unforgettable standout. Her charismatic renditions of songs like "Hook" and "All I Do Is Win" left the audience in awe.

Emma Stone's delightful and charismatic performance not only showcased her playful and versatile side but also endeared her to an even wider fanbase. Her Lip Sync Battle remains a cherished moment in late-night television, forever etching her name in the annals of entertaining and endearing celebrity appearances.

Jimmy Kimmel Calls Out James Corden

In a memorable late-night moment, James Corden and Jimmy Kimmel engaged in a playful yet embarrassing challenge on Corden's show. Kimmel put Corden on the spot by daring him to name just two of his own cameramen or face the consequence of consuming something revolting.

The atmosphere quickly turned awkward as Corden struggled to come up with even two crew members' names, showcasing a moment of unexpected forgetfulness that left the audience in amused disbelief. The challenge highlighted the unique camaraderie between late-night hosts, as well as the delightful unpredictability of live television, underscoring the humor and humility that these entertainers bring to their shows.

Rihanna Pranks Jimmy Kimmel

Jimmy Kimmel, renowned for his love of pranks, found himself on the receiving end of an epic one, masterminded by none other than Rihanna, a self-proclaimed fan of mischief herself. With the stealthy assistance of Kimmel's wife, Rihanna orchestrated a memorable surprise in the early hours.

Waking up to the global superstar herself, the experience was nothing short of unforgettable, etching this impromptu prank as one of the most entertaining and surprising moments in late-night television, and a testament to Kimmel's love for playful antics.

Jason Sehorn Proposes to Angie Harmon

Actress Angie Harmon's appearance on Jay Leno's show took an unexpected turn that turned out to be a heartwarming moment in the public eye. Harmon had been dodging questions about her boyfriend, Jason Sehorn, a New York Giants player, during her interview.

Overwhelmed with emotion, Harmon joyfully accepted, making it a fairy-tale moment. What added to the magic was the presence of her father, who had joined the celebration, turning this unexpected proposal into a genuinely happy ending and a cherished late-night television memory.

Gordon Ramsay's Flirty Banter With Sofia Vergara

Gordon Ramsay's appearance on The Tonight Show took an uncomfortable turn when his behavior towards Sofia Vergara crossed the line. His inappropriate comments, teasing, and even inappropriate touching left the actress feeling uneasy and clearly uncomfortable.

It served as a stark reminder of the importance of respectful and appropriate conduct in any setting, even in the high-spirited world of late-night entertainment, and sparked conversations about the boundaries and expectations of guest-host interactions on such shows.

Kevin Hart vs. Animal Guest

Comedian Kevin Hart, known for his fear of animals, faced his phobia head-on when he joined wildlife enthusiast Robert Irwin on The Tonight Show. Initially, Hart kept his distance from the creatures, but his playful antics included teasing host Jimmy Fallon with a tarantula, sparking laughter from the audience.

The real comedy came when, despite his apprehension, Hart reluctantly took part in a falcon trick, showcasing his hilarious reactions and fear. The segment not only highlighted Hart's comedic talent but also served as a lighthearted reminder of the amusing, unexpected scenarios that can unfold on late-night TV, leaving the audience in stitches.

Whitney Houston's Performance of "I'm You're Baby Tonight"

Whitney Houston's remarkable career made her one of the top-selling artists of all time, having sold a staggering 200 million albums worldwide. On a memorable episode of The Tonight Show, she achieved a historic feat by breaking The Beatles' record with an incredible seven number-one hits.

Houston's stunning live performance of "I'm Your Baby Tonight" on the show left the audience utterly mesmerized. Her remarkable vocal prowess and stage presence reinforced her status as one of the most iconic voices in the history of music, and the record-breaking moment made for a truly unforgettable late-night television experience.

History of Rap with Justin Timberlake

The dynamic duo of Jimmy Fallon and Justin Timberlake has brought a delightful brand of camaraderie to the entertainment world. Their "History of Rap" sketches on The Tonight Show have been nothing short of legendary, featuring their infectious energy, impressive dancing, and playful rendition of popular hip-hop and rap songs like "Crank That" and "Gold Digger."

These sketches became a fan favorite, so much so that they delighted audiences with six installments. Fallon and Timberlake's genuine friendship and their knack for infusing humor and music into their performances have solidified their status as a beloved and enduring partnership in the late-night TV landscape.

Craig Ferguson Becomes a U.S. Citizen

Craig Ferguson's journey from a Glasgow-born comedian to a proud U.S. citizen was not only a significant personal milestone but also a hilarious and heartwarming moment for his fans. Acing the citizenship test with a perfect score of 100%, Ferguson's witty answers and unshakable confidence brought laughter to his viewers.

The moment resonated with many, as Ferguson's journey showcased the possibilities that come with determination and a sense of humor, making us all appreciate the diverse tapestry of America and the dream of a better life it represents.

Ew! with Channing Tatum

Jimmy Fallon's sketch featuring Channing Tatum as Susie was an uproarious hit. Tatum, in full character, not only danced with remarkable finesse but also maintained a straight face throughout. The sketch centered around Susie's disdain for a movie adored by Fallon's Sara, creating a comical contrast.

Their on-screen chemistry was electric, and the audience, as well as the show's guests, were left in stitches by their incredible performance. The seamless interplay between Fallon and Tatum showcased their comedic talents and their ability to create hilarious, memorable moments that have become a hallmark of The Tonight Show.

Steven Colbert’s Tolkien Parody

It's a lesser-known fact that Stephen Colbert made a cameo appearance in Peter Jackson's "The Hobbit" movie series. The comedy host expressed his desire for a spinoff, but Jackson was less enthusiastic about the idea. However, the situation took a humorous turn when Jackson joined Colbert in a playful trailer.

The trailer featured nods to actors from both the Harry Potter and Lord of the Rings franchises, hinting at potential cameos. This whimsical exchange between Colbert and Jackson highlighted their shared sense of humor and the delightful camaraderie that can emerge between fans and creators in the world of film and entertainment.

Will Ferrell and Chad Smith Drum-Off

The phenomenon of celebrity look-alikes often amuses fans, and the resemblance between certain stars is uncanny. Notably, Will Ferrell and Chad Smith, the drummer of Red Hot Chili Peppers, share striking similarities in appearance.

While Chad Smith emerged as the winner, showcasing his musical prowess, Will Ferrell's unexpected talent behind the drum kit left the audience equally impressed. The entertaining face-off highlighted the fun side of these celebrities and gave viewers a unique and unforgettable moment of late-night television.

Jennifer Garner Gets Outsmarted

During an interview with Conan O'Brien, Jennifer Garner corrected his grammar, asserting that "sneaked" was the correct past tense of "sneak," not "snuck." To settle the dispute, Conan resorted to a dictionary, and to Jennifer's surprise, he found "snuck" listed as an acceptable term.

The moment became awkward as Conan humorously pointed out his victory in the language debate, leaving Jennifer Garner and the audience in stitches. It was a lighthearted yet amusing instance of wordplay and grammar correction on late-night television.

Farrah Fawcett Spaces Out

Farrah Fawcett's late-night interview with David Letterman became a topic of widespread speculation as she shared seemingly nonsensical stories, leaving both the host and the audience puzzled. Many viewers were unsure whether Fawcett was under the influence or perhaps playing a unique character.

Nevertheless, her perplexing appearance achieved its goal by generating conversation and intrigue, making it a successful and memorable late-night TV moment that demonstrated the unpredictability and enduring fascination of celebrity interviews.

Johnny Carson’s Last TV Appearance

Johnny Carson's departure from The Tonight Show marked a significant moment in late-night television history. When Jay Leno assumed the hosting duties, the transition was widely discussed and scrutinized. However, what truly stood out was Carson's final appearance on David Letterman's show.

The audience erupted in cheers as the iconic former host sat in the guest chair, showcasing the camaraderie between late-night legends. This memorable moment not only celebrated Carson's enduring legacy but also highlighted the unique bonds shared within the late-night television community, creating an indelible memory for viewers.

Bradley Cooper and Jimmy Fallon Can’t Stop Laughing

A seemingly routine interview on The Tonight Show with Bradley Cooper and host Jimmy Fallon took a hilariously unexpected turn. Both donned comically oversized football visors and wigs, and the laughter quickly became uncontrollable. Fallon even tumbled to the floor, unable to contain himself.

Even after they removed the props, the infectious laughter continued, leaving the audience and the two entertainers in stitches. The sheer absurdity of the situation made it an endearing and memorable late-night television moment that showcased the joyful camaraderie between Cooper and Fallon.

Crosswalk the Musical “Frozen”

"The Late Late Show with James Corden" has become famous for its entertaining "Crosswalk: The Musical" segments, bringing Broadway to the streets of Los Angeles. With the participation of stars like Kristen Bell and Idina Menzel from "Frozen," Corden's portrayals, including one as Elsa, were always a source of humor.

In one memorable twist, Menzel, initially cast as a reindeer, reclaimed her Elsa role by winning a spirited sing-off. The icing on the cake was the cast's dedication, as they enthusiastically wore costumes, making these crosswalk musicals a beloved and hilarious part of late-night TV.

Tattoo Roulette with One Direction

James Corden's show has had One Direction as guests multiple times, treating fans to entertaining segments like Carpool Karaoke and Tattoo Roulette. In Tattoo Roulette, the stakes were high as the band members picked boxes, hoping to avoid a real tattoo. Tension escalated as Niall Horan, the only ink-free member, watched nervously.

Ultimately, Harry Styles ended up with a "Late Late" tattoo, humorously blending it with his existing ink. The amusing game not only showcased the band's camaraderie but also provided viewers with hilarious and unforgettable late-night moments.

Stephen Colbert Gets Touchy With Kristen Stewart

In a somewhat awkward moment on "The Late Show with Stephen Colbert," Kristen Stewart faced unexpected technical glitches when her microphone brushed against her necklace, creating audio problems. Stephen Colbert, ever the problem-solver, attempted to fix the issue by adjusting her necklace, albeit unintentionally making Stewart visibly uncomfortable.

After several attempts, she decided to remove the necklace, resolving the audio problem but leaving a lingering sense of discomfort. The incident showcased the unpredictability of live television and the delicate balance between addressing technical issues and respecting a guest's comfort.

Jimmy Interviews “Khaleesi”

The chemistry between "Saturday Night Live" alumni and Jimmy Fallon often leads to uproarious moments on "The Tonight Show." In one memorable instance, Kristen Wiig portrayed Khaleesi from "Game of Thrones" despite not being familiar with the show.

Her hilarious misinterpretations and imaginative improvisations had the audience and Fallon in stitches. Despite the incorrect answers, the camaraderie and laughter between Wiig and Fallon were infectious, illustrating the enduring charm of SNL friendships and the joy they bring to late-night television.

Cooking With Gordan Ramsay

A culinary showdown unfolded when top chef Gordon Ramsay took on a cook-off challenge with James Corden and his daughter on "The Late Late Show." The unexpected twist came as Corden, known for his comedic talents rather than culinary skills, attempted to surprise everyone with his cooking.

Contrary to expectations, Ramsay faced his own set of challenges in the kitchen, including burning bacon and even causing a pan fire, showing a different side than his usual composed persona on "MasterChef." Surprisingly, Corden's breakfast turned out decent, leaving the audience amused and entertained by the role reversal.

Lip Sync Battle with Tom Cruise

Tom Cruise's appearance on the Lip Sync Battle segment of a show proved to be nothing short of impressive. He energetically performed "Can't Feel My Face," complete with a homage to his iconic Risky Business dance move, sliding to the microphone.

The icing on the cake was The Roots' rendition of "Old Time Rock and Roll," a song famously associated with Cruise's role in the same film. Cruise's lively and unexpected performance delighted the audience, cementing this as a standout moment in late-night television.