Top 10 Celebrity Interviews That Got Uncomfortably Desperate

#10: Joaquin Is Desperate to Remain in Character

“Late Show with David Letterman” (1993-2015)

As an early promotion for a staged documentary, Joaquin Phoenix turns this moment into performance art. He’s deliberately playing a more aloof version of himself. As David Letterman dissects his guest, Phoenix hides behind the beard and sunglasses. Audiences didn’t know what to make of this appearance before it came out as a stunt. The host mostly pokes fun at the actor for his self-serious and stubborn work. Looking back, you see glimpses of the “Joker” star trying to stay in character. His experiment didn’t exactly pan out beyond this curious piece of late-night history. As for getting people to see his movie, the leading man basically failed.

#9: Oliver Stone Talks Putin

“The Late Show with Stephen Colbert” (2015-)

Oscar winner Oliver Stone made a name for himself writing films like “Scarface” and directing “Platoon.” He’s also known for diving into controversial topics, with this “Late Show” interview focusing on his Vladimir Putin project. The director discusses having intimate access to the Russian leader and even seems to defend the man. Drawing backlash from the audience, the guest and his lenient stance on Putin doesn’t garner any support. Stephen Colbert gives the filmmaker a few chances to expand, but the latter’s explanation feels oddly biased. The appearance puts Stone and his political beliefs in a complicated light. In retrospect, this comes off as an artist’s weak attempt to placate a dangerous guy.

#8: Jeff Goldblum Tries to Articulate the Human Experience

“Stephen Colbert’s Live Election Night: Democracy’s Series Finale: Who’s Going to Clean Up This Sh*t?” (2016)

On the night of the 2016 election, many Americans were going through a diverse mix of emotions. Jeff Goldblum tried to articulate his own feelings as a guest on the Showtime special. With host Stephen Colbert guiding him, the actor mustered up some inspiration through the panic. It’s not entirely coherent, but it ultimately ends with a message of positivity. Goldblum might not have been the ideal candidate for that night’s show either. We can’t get mad at somebody for working through their feelings on live TV. In his best attempt to make sense of the world, the “Wicked” star proves that improvising a profound answer isn’t easy.

#7: Chet Hanks Defends His Accent

“Ziwe” (2021-22)

If you know anything about Chet Hanks, you know how this interview will go. Ziwe uses her skills at needling the famous son for his worst ideas. These include thoughts about what accent he can and can’t use. Talking about Jamaican patois, Hanks makes the segment awkward with his bold thoughts. He doubles down on his ability to say anything with whatever voice he deems fit. It’s both shocking and somewhat hilarious in a dark way. There’s something wild about the way he seems to fly in the face of good taste or self-awareness. The host milks the interview for all it’s worth, setting up the man for a crazy appearance that you won’t soon forget.

#6: Alex Jones Can’t Be Contained

“Piers Morgan Live” (2011-14)

He’s the subject of controversy for all sorts of reasons, with a penchant for conspiracy theories. This made his segment on Piers Morgan’s show even more insane. Alex Jones is full of energy, spouting off his beliefs about all things gun control and more. He completely turns the show on its head too. Morgan can barely get a word in edgewise, unable to control his guest. Jones doesn’t do a great job keeping his cool either. At one point, he even employs a British accent. This was all before his more recent run-ins with legal troubles and viral moments. The “Infowars” host and his screaming became even more infamous here.

#5: Norman Mailer Makes Enemies with Everyone

“The Dick Cavett Show” (1968-86)

Unafraid to speak his mind, Norman Mailer becomes the villain of this “The Dick Cavett Show” episode. The author tries to act tough and flex his intellect for fellow guests like Gore Vidal. Unsurprisingly, the other onscreen talent isn’t impressed and neither is the crowd. This leads Cavett to make one of his best quips ever, leaving Mailer largely in the dust. While the writer reels from the verbal setback, he mostly comes off as a pedantic and annoying jerk. He could have saved himself on multiple occasions, but he seems more interested in showing off his ego.

#4: Michael Richards Fails to Clear the Air

“Late Show with David Letterman” (1993-2015)

After his time on “Seinfeld,” Michael Richards tried his hand at stand-up. One awful night onstage turned into a racist rant. He later joined Jerry Seinfeld’s interview on the “Late Show” to apologize, but it only got worse from there. Richards appeared via satellite and awkwardly tried to make his case. With the audience laughing, the actor was helpless to do anything. His career continued to dip afterwards and the performer largely avoided the spotlight for years. For many people, he’s still known as the guy who went from Kramer to a disgraced comedian. This appearance on an ironic talk show was doomed to fail, creating a bizarre moment instead.

#3: Paris Hilton & the NFT Grift

“The Tonight Show Starring Jimmy Fallon” (2014-)

Back when people cared more about NFTs, celebrities seemed desperate to jump on the bandwagon. There’s no better example of this than a soulless ad from Paris Hilton via “The Tonight Show.” Jimmy Fallon helps the guest explain the digital concept, but the audience seems bored of the ape artwork. It goes to show that most everyday people don’t care about something so expensive and intangible. Hilton tries to be cool about it, but she and Fallon come off like two bad salesmen. We can only imagine what the producers were thinking when they tried to make this interview work.

#2: Hugh Grant’s Apology

“The Tonight Show with Jay Leno” (1992-2009, 2010-14)

After being caught with a lady of the night, Hugh Grant went on an embarrassing press tour. This includes one stop at “The Tonight Show with Jay Leno.” You have to hand it to the actor for trying, but there’s no getting around the scandal. He tries to make his case in the face of Leno’s relentless jokes. Grant gives in to the process, knowing ultimately that he’s not wiggling out of this one. The presenter and the audience seem thrilled to be there, but it’s clear that the guest still feels humiliated about his mistake. At the very least, we commend the “Love Actually” star for enduring the trial by comedic fire.

#1: Lester Maddox Embarasses Himself

“The Dick Cavett Show” (1968-86)

Given his controversial reputation, Lester Maddox makes a not-so-fun trip to this show. Dick Cavett allows the southern politician to dig his own metaphorical grave. With guests like Jim Brown next to him, Maddox is outnumbered and eventually decides to leave. This also comes after some clever wordsmithing from Cavett. The host tries to get Maddox to explain himself, but things only get worse from there. After watching this segment, you won’t be surprised to know the governor became a symbol of segregation. This desperate appearance even inspired the likes of Randy Newman to poke fun at it.

Did we forget another celebrity interview that reeks of desperation? Let us know in the comments below.