These Celebs' Old Interviews Are Really Awkward Now

Having a lasting career in Tinseltown can certainly come with a few hiccups. It's hard maturing in front of countless cameras and paps when any sort of old slip-up can come back to haunt our fave celebs forever on the world wide web. Saying one wrong thing can label a star a certain way that sticks, making them seem disinterested, cold, or just plain shady. 

Who can forget actor Shia LaBeouf's rant about how much he hated his second Transformers flick? How about model Cara Delevigne's attempt at sarcasm that just didn't fly with these CBS Sacramento reporters? Although some A-listers have been in the spotlight for years and know how to handle the spotlight's glare, others may just be starting off as newbies in the cutthroat world that is Hollywood. From having your entire family be labeled "talentless" and turning it into a lucrative business, to one actor who made a dicey statement that resurfaced decades later, let's take a trip down memory lane and look at some old celeb interviews that are seriously mega awkward now.

There was a time when Kim Kardashian didn't rule our TV screens — Paris Hilton did. As The Telegraph put it, the heiress is "arguably the Godmother of reality television," thanks to The Simple Life – among the first of its ilk. It was during this series that the world got to know Kardashian, too, as she was working as Hilton's closet organizer. The girls' friendship grew closer in 2006, after Hilton's long-term friendship with Simple Life co-star Nicole Richie came to an end. Kardashian would tell Rolling Stone years later, "We'd go anywhere and everywhere just to be seen."

As Kim K surpassed Hilton as the queen of reality TV, the celebutante made the following shocking claim to Entertainment Tonight (via the Evening Standard): "I created Kim Kardashian. Her whole family owes me life." Bold, no? It's funny that Hilton would make such a daring statement when her own star was slowly declining and Kardashian was busy breaking the internet. Years later, in 2018, Andy Cohen brought the whole thing up his SiriusXM radio show, and Hilton awkwardly avoided answering. That same year, Kardashian even got Hilton to dress up as her "clone" for a Yeezy campaign – a testament to her signature look and worldwide domination.

Who can forget Tom Cruise's declaration of love for Katie Holmes in the form of jumping up and down on Oprah Winfrey's couch? The epic talk show moment has spawned countless memes – much to our sheer delight. Need a refresher on the original moment? We got you. 

Back in 2005, an extremely elated Cruise appeared on The Oprah Winfrey Show, quite literally jumping for joy at the sheer mention of his then-girlfriend, actress Katie Holmes. With every leap on the couch, Winfrey declares, "He's gone. The boy is gone." The action hero finally gushes, "I'm gone and I don't care!" The War of the Worlds star married the Dawson's Creek alum in 2006, but it's the years that followed that made Cruise's outpouring of affection look even more uncomfortable in hindsight. 

Holmes filed for divorce in 2012, asking for "primary residential custody" of their daughter, Suri. The awkward part about the entire separation? Cruise's reaction. Speaking to German TV network ProSieben (via CBS), the actor admitted that he "didn't expect it." Cringe! 

In a showbiz career spanning multiple decades, Madonna sure has perfected the art of throwing shade at her fellow pop stars. Who can forget the time in 2012 when she called Lady Gaga "reductive," before telling her interviewer to look up what that meant and proceeding to take a literal sip of her tea. Talk about savage! In the early '90s, however, the Queen of Pop was much more reserved, perhaps still sharpening her claws while learning the art of verbal annihilation. The shade she threw back then was so subtle, it can only be described as awkward to watch now. 

In the now-cult-like interview at the 1995 MTV Video Music Awards, Madge was busy answering questions — when suddenly a makeup compact goes hurling across the screen. Both the interviewer and the starlet look down below and spot Hole frontwoman Courtney Love. The host asks Love to join the chat. Madonna mutters, "No, don't, please," but Love is already on her way up. A helpless Madge mumbles, "Courtney Love is in dire need of attention right now." Yikes! As Love sits next to the "Like a Virgin" starlet, sheer awkwardness ensues, with Love even calling Madonna out for saying something "mean" about her in a recent interview. This is iconic to look back at now, but totally cringe-worthy nonetheless.

Plenty of folks are familiar with Jerry Seinfeld's exceptionally uncomfortable 2017 red carpet run-in with Kesha – the one where he denies her a hug not once, but three times! Fans were horrified, Kesha included, who later told radio station Hits1: "He's not a huggy guy, that's fine. I shoulda known better, I've seen the hugging episode!"

Another person who should know better? Larry King, who had his own painfully awkward encounter with the comedian in 2007 on CNN's Larry King Live. The talk show legend made the mistake of asking if Seinfeld's eponymous series had been canceled. Granted, King probably should have known that the funnyman chose to end the series while he still had the "number one show in television," reportedly turning down an offer of $5 million per episode from NBC, but Seinfeld was downright appalled that King wasn't up to speed. "You're not aware of this? ... You think I got canceled?" Seinfeld exclaims. King asks if he's upset him, and Seinfeld's signature sarcasm makes it clear that he has. 

Years later, King talked about that awkward situation on The Young Turks. "[Seinfeld] later said he wasn't mad, but he was mad ... I should have known that, but I was stupid."

The '60s were undeniably a different time in the world, with the concept of modern feminism only slowly creeping its way into the mainstream. Meanwhile, the epitome of masculinity on the silver screen was James Bond, played by Sean Connery at the peak of his 007 fame. In a 1965 interview with Playboy (via Sean Connery: A Biography), the Scottish actor was asked, "How do you feel about roughing up a woman, as Bond sometimes has to do?" Connery's response is jaw-dropping. "I don't think there's anything particularly wrong about hitting a woman," he said. "If a woman is a b***h, or hysterical, or bloody-minded continually, then I'd do it." 

As much as we might want to chalk this up to awkward 1960s-style chauvinism, the star sealed his fate in 1987 during an interview with Barbara Walters. Bringing up his statement from so many years ago, the famed journalist tells the Goldfinger celeb she "didn't love that." An unphased Connery responds: "I haven't changed my opinion ... I don't think it's that bad." Uh, what? He goes on: "I think that it depends on the circumstances  ... they want to have the last word and you give them the last word, but they're not happy with the last word. They want to say it again and get into a really provocative situation. Then I think it's absolutely right."  

When Keeping up with the Kardashians launched in 2007 on the E! Network, the world instantly becoming mesmerized with the clan that's now casually referred to as America's royal family. Around Season 4, famed journalist Barbara Walters put the entire family on ABC's 18th annual "10 Most Fascinating People" special. Clearly, the KarJenners had already garnered some haters at this point because Walters opened her segment with: "I have never heard more anger or dismay then when we announced that the people you're about to see were on our list." Yikes.

Sitting down with Kim, Kourtney, and Khloe Kardashian and momager Kris Jenner, Walters starts her interview with the following blunt statement: "You don't really act; you don't sing; you don't dance. You don't have any — forgive me — any talent." Seemingly unphased by the statement, Khloe declares, "But we're still entertaining people." After some back and forth, the youngest Kardashian sibling actually ends up agreeing with the host! "None of us think we have talents," she says. Oh, okay. 

Fast forward a few years and the KarJenners are more famous than ever. Kylie Jenner and Kim K have their makeup empires; Kendall was the highest-paid model in 2018; and Khloe launched Revenge Body, her own fitness reality TV show. As for Kourtney? In 2019, she debuted Poosh, a Gwyneth Paltrow-style lifestyle blog. Not bad for a "talentless" family.