20 Late Night Show Guests Who Made It Hard To Look Away

late night television shows are typically where the fun is the audience anticipates their favorite celebrity gracing the stage to join the show's host with a light-hearted and Casual Vibe entertaining them and viewers at home with jokes and fun drama but there are certain instances when that's not the case sometimes the mood unexpectedly shifts from jovial to insulting provocative or derogatory this is usually because the host or guest says or does something that catches the audience off guard making it hard for them to look away here are 20 such instances that'll have you wondering how bizarre some celebrities and even politicians can get number 20 Drew Barrymore to start off on April 12th 1995 David Letterman celebrated his 48th birthday in a very memorable way thanks to actress Drew Barrymore at the time Drew was a former Child star who had just turned 20 her career was thriving with movies like Boys on the Side mad love and Batman Forever on the horizon Letterman began the interview by discussing Drew's recent birthday and she responded that it was the first birthday she had truly enjoyed the conversation then took a surprising turn when Letterman asked about rumors of her visit to a New York club called the Blue Angel known for its provocative performances Drew who had previously posed nude for Playboy admitted that she had performed a strip teas for patrons at the club Letterman inquired further and Drew decided to demonstrate what she had done that night with Paul Schaffer providing some music for the scene she climbed onto Letterman's desk danced provocatively and lifted her shirt to flash him all while wishing him a happy birthday the spontaneous performance was seen not only in the Ed Sullivan Theater but also on a giant screen in Time Square it became an iconic moment in late night TV and a turning point in Letterman's Late Show tenure looking back on the incident Drew praised Letterman for his handling of the situation stating that he made her feel comfortable during and after the impromptu dance the two jokingly referenced the moment in her later appearances on the show as well number 19 Matt Damon back in 2008 Matt Damon found himself in the middle of a long-running joke on Jimmy Kimmel Live the joke was that Kimmel always ran out of time and never got to interview Damon in response Damon always promised to get his revenge for being snubbed by Kimmel so many times to make his revenge sting even more Damon got Sarah Silverman involved at the time Silverman was Kimmel's girlfriend together they planned an unforgettable payback on national TV their plan was pretty wild Silverman went on the show and admitted to cheating on Kimmel with none other than Matt Damon she even took it a step further by confessing that she had written a song about it this shocking Revelation happened on an episode of The Late Night show and it completely caught everyone offg guard including Kimmel himself he struggled to hide his genuine discomfort behind forced Smiles even though it was just a joke between friends it was a pretty serious prank but the next guest on our list had an interview that was both funny and strange and it was none other than the ex-president Barack Obama number 18 Barack Obama Jimmy Kimmel's famous mean tweet series is a hit among viewers in these segments celebrities read and react to harsh comments from Twitter trolls these videos entertain audiences as stars acknowledge the often unkind online remarks usually they respond in good spirits and sometimes they even strike back at the mean comments one mean tweet segment though was extra special it featured President Obama as a two-term President Obama endured a lot of criticism but in this segment he took it a step further by publicly acknowledging some of the most vicious insults aimed at him it was clear that Obama had a great sense of humor as he participated in this light-hearted bit Obama delivered each mean tweet with comedic finesse even sharing a laugh laugh at the absurdity of some of the insults what made it even more enjoyable was when he fired back with witty retorts to the commenters sadly as his presidency ended we missed out on seeing him in more of these entertaining segments but don't worry there are still plenty of other guests to keep us entertained like the next Superstar on our list number 17 David Letterman during the taping of his show David Letterman decided to share a personal and rather serious story with his live studio audience the 62-year-old comedian at the time recounted a harrowing 3-week ordeal during which he was the target of a blackmail attempt Letterman revealed that someone had threatened to expose his affairs with female members of his staff unless he paid them $2 million throughout his narration Letterman's emotions shifted between humor seriousness and occasional nervousness the comedian explained that he discovered a disturbing package in his car one morning concerned he and his legal team immediately contacted the Manhattan District Attorney's office for assistance the District Attorney's office confirmed the authenticity of the blackmailer threats and devised a plan to catch him they set up a sting operation involving a counterfeit check which ultimately led to the successful arrest of the culprit the blackmailer was identified as Robert halderman a 51-year-old Emmy winning producer who worked for CBS on the show 48 Hours it later emerged that halderman had recently been in a relationship with Stephanie burkette Letterman's personal assistant and an occasional character on his show allegedly extracts from burkett's Diaries were included in the incriminating package sent to Letterman the motive behind the extortion attempt against David Letterman took a rather funny turn the blackmailer threatened to turn Letterman's actions into a screenplay Letterman during his onair confession revealed that the man planned to make a movie about all the terrible things he knew about his life throughout his confession Letterman appeared visibly terrified and guilty he tried to move past the experience but expressed his need to protect his family his reputation and his job but the Revelation that he had engaged in relationships with employees or those under his management opened the door to potential sexual harassment lawsuits both for him and for CBS This startling confession gave the Network's legal team plenty of reasons to lose sleep Letterman's unexpected Revelation didn't just provide material for other comedians to make jokes it also left him questioning his choice of naming his production company worldwide pants if you think Letterman's case was messed up wait until you hear what happened in the next celebrity interview number 16 Nicole Kidman during Jimmy Fallon's interview with Nicole Kidman they remembered past experiences Jimmy shared his recollection of a prior encounter with the Hollywood star but the conversation took an unexpected turn when Kidman revealed something no one had known before she confessed to having a genuine interest in Jimmy and her desire to explore the possibility of dating him in pursuit of this romantic adventure she had even approached a mutual friend to help set them up apparently the meeting finally happened but Jimmy's Focus was far from the Romantic hangout Nicole had been hoping for instead he was more preoccupied with playing video games in his apartment which derailed any potential Sparks between them it was a moment that could have changed their lives forever but ended in a missed opportunity years later Nicole Kidman shared this Revelation on Jimmy's own show catching him off guard he was not only flustered but left short circuited by the recollection of his past mistake things got so heated that Jimmy had to sprawl out on a couch and think about his life while all of this unfolded on live television speaking of intensity the next late night show guest took things way too far number 15 Richard Simmons some people find Richard Simmons hilarious but others might find him a bit overwhelming his flamboyant person ality and Boundless Energy can sometimes push the limits of what people can tolerate one person who seemed annoyed by Simmons Antics was late night talk show host David Letterman in 2006 during one of Simmons's visits to Letterman show he was there to promote a food steamer but there was a lot of discomfort in the air as Simmons tried to explain the product Letterman couldn't resist poking fun at him as he often does with his guests but the real surprise came later in the interview when Simmons started demonstrating how the steamer worked when he pressed the power button something unexpected happened the steamer started releasing a lot of smoke and then it caught fire Simmons panicked and jumped out of his chair his enthusiasm turning into sheer Terror surprisingly Letterman remained seated laughing heartily it turned out that he had orchestrated the whole incident as part of an elaborate prank regardless of the accident the show went on and it certainly made for memor able television number 14 Andy Dick before his arrest for sexual battery Andy Dick made headlines in 2007 for an incident involving Ivanka Trump on Jimmy Kimmel Live in the footage a 52-year-old dick greeted Trump and host Jimmy Kimmel he inappropriately touched her legs while commenting on the glitter on them Trump who was 36 at the time looked shocked but tried to laugh it off while Kimmel intervened asking dick not to touch Ivanka Kimmel even humorously warned that Donald Trump would be unhappy with their interaction security eventually removed dick from the stage after the episode aired Kimmel explained that dick had been a little out of it and had wanted to kiss Ivanka he remembered escorting dick out emphasizing that dick wasn't upset or apologetic simply describing him as nutty in December 2017 Andy brought up the incident on his Instagram account offering a bizarre explanation he claimed that he was jokingly carried off by security and that he had mistakenly thought Ivanka would date him but Dick's actions have not been limited to this incident in 2018 he faced legal action after being charged with misdemeanor sexual assault and simple battery related to a separate incident in Los Angeles this case involved allegations that he assaulted a Woman twice and made derogatory comments toward her in an October 2017 article in the Hollywood reporter dick revealed that he had harassed people in multiple ways on the set of the independent feature raising Buchanan he was also fired from the low-budget comedy vampire Dad after similar allegations dick has denied some of the groping accusations but admitted to licking people and making propositions number 13 Larry King throughout his career Larry King engaged in conversations with many top figures including Sir Paul McCartney Barack Obama Oprah Winfrey Prince Elizabeth Taylor and Frank Sinatra but one of the interviews that left a lasting impression on him was the encounter with Marlon Brando in 1994 King paid a visit to the iconic actor at his Los Angeles residence a week after sharing lunch with Brando it seemed that the iconic actor had reluctantly agreed to the interview not without a condition he wanted to have a pre-interview lunch with the host although King typically directed the conversations in his interviews Brando adopted a more playful approach he interrupted King's questions playfully pinched his nose and even persuaded King to join him in a duet before leaning in for an unexpected kiss on the lips this encounter continued to resonate with King for years thinking back on the experience he praised Brando as a brilliant and marvelous individual number 12 Michael Richards Michael Richards the star of Seinfeld appeared on The Late Show with David Letterman to offer an apology and explanation for the racially offensive rant he went on during a standup comedy performance the 57-year-old actor expressed deep regret for his outburst and denied being a racist with frustration in his voice Richards remembered that he had spiraled into a rage due to audience members interrupting his act at the Laugh Factory in West Hollywood during the interiew interview Richards grew annoyed when the term African-American got the audience laughing making him question if it was the right platform to address the situation this interview aired on the CBS show along with a segment featuring Richard's former co-star Jerry Seinfeld Seinfeld had earlier expressed his distress over the incident and encouraged Richards to make a satellite appearance on Letterman's show to address it while some in the audience laughed during the rant others gasped in disbelief and a spectator pointed out that it was not funny suggesting it might negatively affect richards's career number 11 Jerry The King Lawler and Andy Kaufman back in 1982 an episode of Late Night with David Letterman hosted Jerry The King Lawler and Andy Kaufman but putting them on screen together proved to be a bad idea Kaufman known for his unique standup comedy took an unexpected turn in his career by becoming a wrestler his wrestling Persona included scripted performances distinctive story lines and over-the-top personalities all reflecting his sense of humor behind the scenes Lawler and kofman were friends and collaborators but in the public eye they played Rivals Kaufman regularly taunted Lawler and his hometown of Memphis but it was all part of their spectacle with Kaufman still wearing a neck brace they appeared on Letterman's show during the televised interview Lawler couldn't resist delivering a series of taunts humorously suggesting that Kaufman's parents were both satisfied with his gender at Birth Kaufman initially softspoken claimed that Lawler was merely playing the role of a bad guy wrestler he even asked for an apology from Lawler who dismissed it accusing Kaufman of seeking attention and claiming that his injuries weren't real somewhere in between Lawler slaps Kaufman and things go off the rails tensions escalated during the interview to the point that Kaufman hinted at legal action over his supposed injuries but nothing has been living rent-free into our minds like the next guest appearance we're going to show you number 10 Angie Harmon during an interview with Jay Leno actress Angie Haron daughter of executive Lawrence Paul Harmon had an unexpected turn of events it start started like every other interview with small talk and banter setting the tone for the rest of the conversation Jay in his typical straightforward style then decided to inquire about her relationship status this made Angie almost instantly uncomfortable and she claimed that she doesn't normally talk about her personal life still she confirmed that she was dating someone seizing the moment Jay suddenly called Jason onto the stage har kman was just as confused as everybody else but still clapped as her boyfriend made his way to the stage but what happened next changed everything Jason a former giant cornerback dropped to one knee and before a live audience proposed to Angie it had people swooning when she enthusiastically accepted the proposal Angie was seated with one hand covering her mouth barely able to speak as Jason put a ring on her finger this impromptu Act of Love led to a marriage that endured for 15 years spanning from 2001 to 2016 but while some late night show guests spread love others can't stop picking beef with the hosts another celebrity appearance that stirred controversy on The Late Show with David Letterman was that of Crispen Glover and it was very strange number nine Crispen Glover during the promotion of his movie River's Edge in 1987 Crispen Glover made a memorable appearance on Letterman's late night show he showed up wearing platform shoes long striped pants and unusually long hair things took a strange turn when Glover offered to arm wrestle Letterman which the host declined but Glover then delivered a kick only inches away from Letterman's face after which he abruptly ended the segment Glover's Behavior raised suspicions of recreational drug use but in a 2014 Radio interview Glover clarified that his behavior was not drug induced instead he explained that it was an attempt to redirect the interview that seemed to be going off course despite his explanation his conduct has never been entirely Justified several years later in 1991 Glover released a film titled Ruben and Ed during another appearance on Letterman's show he came dressed as his character from the movie and acted as the character throughout the interview at first his behavior was strange then it became obvious that Glover was essentially embodying a different personality given his relatively lower profile compared to other celebrities Glover's appearance could be seen as copying waen Phoenix's strange interview in I'm still here but nothing had people talking like the next person on the list number eight Lily Tomlin in the year 1972 there was a TV show known as the dick Cav show during one of its episodes a well-known actress and comedian named Lily Tomlin was a guest she was famous for her funny performances on shows like Rowan and Martin's Laughin and later Saturday Night Live also on the show that day was Chad Everett who was recognized for his role in the movie Medical Center after Lily finished her conversation with Dick the host of the show she moved to a different chair this was a common thing to do on talk shows like this one then dick began chatting with Chad every now and then he would say something to Lily during their conversation but things took an unexpected turn when Chad started telling jokes that made Lily upset she didn't find them amusing at all so without warning she abruptly left the stage despite attempts from both dick and Chad to persuade her to return one of the jokes that upset Lily was about Dick's wife whom Chad compared to an animal owned by dick following this dick made more jokes suggesting that his wife preferred being taken care of by a man not a woman like Lily these remarks only serve to heighten the discomfort of the situation the atmosphere in the studio became tense with the audience growing silent this indicated that not only did they disapprove of what was happening but the live audience also felt uneasy about the unfolding events none of those seated at the audience could forget it and it is still talked about today number seven Piers Morgan in 2021 an unforgettable moment happened on live television when Piers Morgan a presenter suddenly left the set of Good Morning Britain what caused his departure was a confrontation initiated by the weather presenter Alex barisford Alex addressed peers regarding comments he had made about Megan markle's interview with Oprah Winfrey during the previous day's broadcast Alex expressed his Viewpoint saying he understood that Piers had a personal relationship with Megan Markle and she cut him off he added that Megan Markle is entitled to cut him off if she wanted to Alex then said Megan hasn't said anything about peers since she cut him off yet peers continued to trash her online and to other celebrities in response to Alex's remarks Pier stood up and left the studio marking his final appearance on the show later that day it was announced that he would be departing immediately due to the controversy surrounding his comments about the duchess number six Richard Branson in 2007 billionaire Richard Branson appeared on The Colbert Report to promote his new business venture Virgin America airlines after a brief chat with coar the segment ended without Branson getting a chance to promote his airline by name it appeared that Branson might have felt short changed and in a moment of frustration he playfully splashed colar with water from his mug both colar and Branson managed to hide their true feelings of annoyance but the tension was obvious from their expressions to settle the score colar retaliated by having a staffer fetch a bottle of water which he used to reciprocate the splash ending the tension that had plagued the entire segment there have been spec speculations that the incident may have been staged and even to this day it remains unclear whether it was a spontaneous moment or a pre-arranged stunt but if you think this was mean wait until you hear about the next guest on this list number five Heidi Clum Heidi kum's appearance on The Tonight Show with Jay Leno in 2003 was supposed to be Unforgettable she was set to do a real strip tease on live television wearing a diamond studded bra from Victoria's Secret valued at $8 million paired with a matching pair of knickers that cost $3 million every detail was real with no fakery involved but just before the planned strip teas There Was An Unexpected problem during Loo's interview with Clum she suddenly stopped midc conversation she expressed her suspicion that her luxurious bra had come undone beneath her shirt caught in a moment of uncertainty Clum grabbed her shirt Unsure how to proceed luckily comedian Martin Short was also a guest on the show that day together with Leno they improvised a solution using their suit jackets they shielded Clum from the studio audience giving her the Privacy she needed to check on the wardrobe malfunction the show briefly paused to address the situation to the audience's Delight the strip teas still happened later in the show but as embarrassing as this moment was for Clum the next guest on our list had an even wor worse mishap let's get right into that number four Hugh Grant in June of 1995 Hugh Grant still an upand cominging movie star about to launch his major film 9 months had a legal issue the police arrested him for engaging in sexual activity with Divine Brown a well-known Hollywood sex worker in a public place Grant chose to plead no contest to the charges but the incident was so Infamous that it spread like wildfire dominating headlines scheduled to appear on The Tonight Show to promote his upcoming movie Grant confronted Jay Leno amid the Brewing Scandal to Leno's credit he didn't tiptoe around the issue instead he asked the question that was on everyone's mind which was what was he thinking in such situations many celebrities offer a laundry list of excuses or claim innocence urging viewers to wait for all the facts but Grant took a different approach by being candid he didn't make excuses and he openly admitted to his wrongdoing describing it as a bad thing in this context his honesty was refreshing this conversation between Leno and Grant brought forth a rare moment of vulnerability and authenticity in the world of celebrity interviews it showed that taking responsibility for your actions isn't a bad thing after all number three Madonna Madonna's appearance on David Letterman's show in 1993 was far from ordinary this was before her British transformation and her entrance was a blend of Hollywood's Golden Era and the rebellion of New York cbgb's punk scene as soon as she strolled in she greeted Letterman by dubbing him as the man who has his finger on the pulse of total strangers but things quickly escalated from there the interview started with a humorous taunt as Madonna joked that she was only there because a Knicks game wasn't airing but what seemed like a typical talk show segment took an expected turn when David asked Madonna to kiss a man in the audience Madonna refused and decided to drop an F-bomb a daring move on television at the time throughout the interview Madonna artfully evaded and redirected every question David threw at her leaving him visibly flustered her Charisma was contagious and the audience was captivated by her presence the exchange between the two involved witty banter and numerous awkward silences creating a strange yet addictive atmosphere Madonna didn't hold back calling out David for prying into her intimacy habits and accusing him of excessive flattery toward his guests but Madonna's bold behavior on the show was not without context in the leadup to her appearance Letterman had indulged in a series of jokes about her liberated intimate life and Madonna took notice she addressed it by saying that he can't get through a single show without talking about her or at least thinking about her now Madonna's confrontation was unusual but wait till you see just how unexpected the next one was number two Paris Hilton in 2007 Paris Hilton caught everyone's attention because of some legal troubles that landed her in jail for driving with a suspended license after she was released she wanted to move on from that and focus on her career especially her clothing line and a new perfume she was launching to promote her new projects Hilton went on David Letterman's show but things got uncomfortable pretty quickly as soon as the interview started Letterman started asking Hilton about her time in jail at first Hilton tried to laugh it off but Letterman kept asking more intrusive questions and even joked about her being in jail Hilton got frustrated and told Letterman that she didn't want to talk about it anymore because she had moved on with her life but Letterman didn't stop to he kept pushing the issue and the interview became one of the most awkward ones ever on TV her top was already a risky choice but she probably didn't expect this to happen on live TV now on to our last strange guest number one Wen Phoenix when waen Phoenix portrayed himself as someone undergoing a public breakdown in pursuit of a rap career in his film titled I'm still here it stirred controversy the the movie A biographical project co-produced with Casey Affleck during their close friendship faced scrutiny mainly due to allegations against Affleck during the filming process despite the controversies surrounding the film Phoenix's dedication to his onscreen and off-screen Persona was obvious during his 2009 appearance on The Late Show with David Letterman but during this appearance Phoenix maintained a low profile offering mumbled responses and allowing David to playfully mock him and his unconventional Behavior some viewers found it annoying and even rude for Phoenix to behave that way with the show's host in later years Phoenix returned to the show seemingly as a gesture of reconciliation and it appears that their relationship has since improved but when the initial interview with the joker actor aired it became a topic of widespread discussion which of these guests or hosts do you think went too far share your thoughts with us in the comments thank you for watching this video Until the End and we hope you join us again in the next one don't forget to subscribe to our Channel and check out our other uploads if you enjoyed this video

Channel: Prime Discovery

Views: 6,556

Keywords: 20 Late Night Show Guests, Who Made It Hard, To Look Away, 20 late night, show, guests, hard, look, away, iconic, legendary, entertaining, controversial, unforgettable, appearances, history, TV

Id: Blc9QJCsdKQ

Length: 29min 45sec (1785 seconds)

Published: Sat Jul 13 2024