Top 10 Celebrity Interviews That Didn't Age Well
#10: Jennifer Aniston
Top 10 Moments That Made Us Love Jennifer Aniston
"Late Show with David Letterman" (1993-2015)
People today can barely grasp the pop culture phenomenon that was Jennifer Aniston's hair. During her 1998 "Late Show" appearance to promote "The Object of My Affection", David Letterman went too far with the object of fans' affection. He broke a moment of silence in the conversation to say: ["Forgive me if this is rude. I just want to try one thing."] He then pulled a length of Aniston's hair into his mouth. It was a jarring stunt with a beauty icon's signature do. The gag was brushed off for years until Letterman's notoriously mean-spirited interview with Lindsay Lohan in 2013. The incident with Aniston is now seen as indicative of Letterman's unsettling treatment of women. Aniston didn't seem very amused at the time.
#9: Taylor Swift
Top 10 Hilarious Taylor Swift Moments
“The Ellen DeGeneres Show” (2003-22)
During Ellen DeGeneres’s reign as the “Queen of Nice,” the harsher jokes on her talk show were generally taken in good spirits. Taylor Swift seemed to be the only one who didn’t take her 2012 interview in that way. First, DeGeneres kept poking at disputed rumors that she dated Zac Efron. Referencing the pop star’s prolific love life, DeGeneres eventually dragged Swift into a game where she would identify her exes in a photo slideshow. The audience laughed hysterically as Swift became visibly upset. Their tune finally changed in 2021, when allegations of workplace hostility caused DeGeneres’s fans to reappraise her public persona. Her grilling pop music’s Queen of Nice for her personal life stood out as a red flag that everyone just shook off.
#8: Dolly Parton
Top 10 Times Dolly Parton Was Awesome
“The Tonight Show Starring Johnny Carson” (1962-92)
Johnny Carson revolutionized banter for a late-night audience. His crude flirtations were considered fairly inoffensive for the time. Now, audiences have particular trouble getting over a Dolly Parton appearance in 1977. It’s awkward enough that the conversation steered toward dismissing rumors that she had work done on a certain area of her body. Carson tried to be a quiet gentleman, until he blurted out: [“I’d give about a year's pay to peek under there.”] The audience burst out laughing, as did Parton herself. With the racy chat’s light tone, it’s easy enough to accept the joke as a product of its time. But wanting to inspect a popular rumor about country’s biggest heartbreaker still gets a more reluctant laugh nowadays.
#7: Madonna
“Late Show with David Letterman” (1993-2015)
Similarly, many David Letterman interviews with women haven’t aged well. Madonna’s 1994 appearance on the “Late Show” was controversial at the time, but maybe for the wrong reasons. Most of her record 14 censored f-bombs were in response to Letterman continuously joking about her sex life. His suggestion that she go kiss a random man in the audience was particularly creepy. The interview quickly became an iconic scandal for “Late Night” because of the pop idol’s salty language. Modern audiences now find that easier to accept than Letterman’s sleazy spoofing of her unladylike candor. The fun in Madonna pushing edgy women forward is now spoiled a bit by Letterman and his ‘90s audience’s attitude about it.
#6: Bill Cosby
Celebs Who Tried to Warn Us About Bill Cosby...
“Larry King Live” (1985-2010)
Bill Cosby’s 2018 conviction for sexual assault permanently warped his legacy. He actually may never have been that wholesome. While multiple women were coming forward with accounts of being drugged and assaulted, Cosby’s 1991 interview on “Larry King Live” resurfaced. The comedian bantered about the disputed aphrodisiac Spanish fly, and described slipping it in women’s drinks to lower their inhibitions. It’s hard to imagine anything humorous about these comments even for the time. They were bad enough for the prosecution in Cosby’s trial to push to have them admitted as evidence. This request was denied because Spanish fly is not a sedative. Still, with the way Cosby talked about it, there’s also more weight to his one-liner, “Hello, America!”
#5: Anne Hathaway
Top 10 Moments That Made Us Love Anne Hathaway
“Today” (1952-)
Matt Lauer's sketchy interactions with women were seriously reappraised after allegations of sexual misconduct got him fired from "Today" in 2017. His 2012 interview with Anne Hathaway especially stands out. The future Oscar winner was promoting "Les Misérables" when Lauer immediately brought up her wardrobe malfunction at the movie's New York premiere. As she tried to tastefully move past this humiliating topic, Lauer kept it going. He might have been noble in his criticism of the paparazzi profiting off of people's vulnerability. But with her obvious discomfort, Hathaway seamlessly segued this discussion into her character of Fantine. The irony in Lauer condemning sexualized exploitation would become clear not five years later. His reputation now makes Hathaway's already awkward interrogation downright cruel.
#4: Ricky Martin
Top 10 Celeb Reactions To Ricky Gervais Roasts
"20/20" (1978-)
Latin pop sensation Ricky Martin endured years of gossip about his sexuality before he formally came out in 2010. Where most interviewers respected his privacy, Barbara Walters saw it as another big scoop. In an ABC interview in 2000, she accosted Martin about the rumors. She eventually asked him point-blank to declare whether he's gay. Martin simply responded: ["I just don't feel like it."] It would be another ten years before he was ready to tell the world his truth. Shortly afterward, Walters named trying to out him as the biggest regret of her career. Martin himself remembers the incident as permanently traumatizing. What once was an edge-of-your-seat tabloid standoff is now widely condemned as a violation by a respected journalist.
#3: Corey Feldman
“The View” (1997-)
Clearly, Barbara Walters’s confrontational interview style could dig a bit too deeply into personal lives. When Corey Feldman appeared on “The View” in 2013, she tried to bury an important subject deeper. The actor was promoting his memoir “Coreyography,” in which he alleges that many entertainment industry leaders sexually assaulted him when he was a minor. Friend and fellow victim Corey Haim’s own allegations had been met with skepticism for years before his death. Even with Feldman’s courageous confession, Walters responded with: [“You’re damaging an entire industry.”] Her victim-blaming was immediately controversial, but the fuss soon died down. With the rise of the MeToo movement, Feldman’s already uncomfortable scrutiny has resurfaced as a horrific stain on Walters’s otherwise distinguished career.
#2: Danny Masterson
10 Celebrity Reactions to the Danny Masterson Verdict
“Late Night with Conan O'Brien” (1993-2009)
Danny Masterson’s history of sexual assault resulted in his conviction in 2023. This has permanently colored his legacy, as well as his off-color sense of humor. One joke during a 2004 appearance on “Late Night” is now particularly ominous. The star of “That ‘70s Show” mentioned an impression of him by Bodhi Elfman, whose go-to line was: [“Hi, my name is Danny Masterson. Would you like to touch my balls?”] Host Conan O’Brien appeared to be joking himself when he asked Masterson why he introduced himself that way. He ended the conversation with, “I’ve heard about you. And you’ll be caught soon.” With Masterson’s crimes going back to 2001, O’Brien might not have been joking. Either way, “soon” wound up being 19 years.
#1: Britney Spears
Top 10 Britney Spears Interviews We Look at Differently Since Reading Her Memoir
“Primetime” (1989-2012)
It took too long for the public to take pop legend Britney Spears's mental health seriously. One notably reframed chapter in her downfall is a 2003 interview for ABC's "Primetime." Diane Sawyer dug into outrage at Spears over her breakup with Justin Timberlake, whose crude behavior has since come under scrutiny. The beauty icon was also scolded about her sexualization, shopping habits, and nervous tics. After the interrogation brought Spears to tears, she became a laughingstock. But the MeToo movement revealed the extent of the alleged exploitation from her representation and father. She couldn't do much shopping when she was too depressed to leave her apartment. Though the "Primetime" interview is now considered the tragedy it was, Sawyer has yet to apologize to Spears.
What classic celebrity interviews do you think have taken on a different meaning over the years? Let's chat in the comments.
