Top 10 Celebrity Interview Moments That Aged Badly

While some people remember Madonna's censored outbursts during this show, they sometimes forget the context behind it. Letterman spends much of this interview egging on the pop star with personal questions. He even asks if she would go into the crowd and kiss one of the audience members. We know the host has a reputation for pushing the envelope, but we've come a long way since the ‘90s. And can see the more problematic elements behind the chaos and banter in this exchange. Still, Madonna holds her own and speaks her mind, fighting back against the presenter in a truly off-the-wall scene.

Cara Delevingne was promoting her film "Paper Towns" in this interview, but it was quickly muddied by some shallow questions from a morning show crew. The interviewers asked whether Delevingne even read the book and asked if she had enough time to even consider doing so. After some more questions and playful jabs, another anchor comes out with a misplaced critique of the actress’ behavior. He tries to say that she doesn't seem all that excited, and the performer is understandably taken aback. She handles the moments with humor and grace, but the news team from "Good Day Sacramento'' does not come off well in this clip.

Lindsay Lohan's personal life is the subject of this appearance on the "Late Show with David Letterman." Her run-ins with the law quickly become the main topic of this interview. But it’s when he brings up her impending trip to rehab, the host steps over a boundary. Letterman inappropriately tries to unearth details that are none of anyone’s business. Lohan isn't sure what to say in response to the host's awkward line of questioning. Poking fun and prodding when it comes to someone’s struggles with addiction certainly wasn’t okay then, and it isn’t okay now.

Diane Sawyer's "Primetime" interview with Britney Spears is now largely panned for its negativity. More akin to an interrogation, the journalist turns the exchange into a focus on the pop star's faults. Sawyer questions her image, her relationship with Justin Timberlake, and her viability as an artist. Looking back at the tape, the interviewer’s techniques feel harsh and aggressive, especially considering the star’s young age. Our hearts absolutely break seeing the singer in tears following the mounting scrutiny. Spears herself later admitted that she felt the interview was unfair. Needless to say, most people agree that Sawyer’s actions contributed to a growing harmful media circus surrounding her.

Jennifer Aniston appeared on the "Late Show with David Letterman" with a hairstyle that seemingly caught the host's attention. And he inexplicably thought it’d be okay for him to slide over in his chair with little warning and bite down on a strand of it. It goes without saying, but the actress is visibly flustered by the move. She tries to play it off as a joke despite her obvious discomfort. It's hard to imagine that this kind of behavior would happen at all today without both parties signing off on it. Letterman even mentions her reaction and jokingly shifts the blame to her, making this all the more questionable after the fact.

This Ben Affleck interview captures a particularly controversial moment in his history with the press. With interviewer Anne-Marie Losique on his lap, Affleck gets up close and personal in a series of cringe exchanges. He also jokes about wanting her to wear more revealing clothing in one of several comments that are too intrusive. The video resurfaced in the wake of the #MeToo movement, as the actor's actions were further examined. His handsy behavior and questions about the TV personality's relationship status came into focus, and people didn’t like what they saw. Losique later clarified that this scene was played up for the cameras, but it still hasn't aged well at all.

The late Sean Connery was widely known as a macho man, and he remained set on that persona. But his antiquated views on gender were bad back in the day, and they’ve just aged extremely poorly since. When he sat down for an interview with Barbara Walters, the “James Bond” actor discussed his controversial views on men and women. Walters asked Connery about his previous statements regarding assaulting members of the opposite sex. Given the chance to recant his opinions, the actor doubled down on his problematic stance. His further views on equal rights and even golf didn't inspire confidence either.

Brian Williams was known as the trusted anchor for the "NBC Nightly News" for many years. During this Letterman interview, he discussed an experience riding in a helicopter while covering the Iraq War. It was later discovered that his claims were embellished. He weaves a rather elaborate tale for Letterman, which would be fine, except he wasn’t actually in the aircraft that was hit by an RPG. This fabrication led to his suspension from NBC and ultimately his departure from his coveted position at the network. Although he later worked at MSNBC, the presenter saw a considerable drop in his reputation because of this scandal.

After the bombshell revelations about him, almost every Harvey Weinstein interview plays out like a failed lie detector test. This one in particular showcases the depth of his hypocrisy given the extent of his crimes and allegations. The producer goes on to describe himself as an "underdog," wanting to create projects that celebrate people like him that struggle. Knowing anything about Weinstein's awful behavior, it's plain to understand that he’s the furthest thing from a movie hero. He instead used his power to prey upon real underdogs for his own personal gain. Most of this video reveals the front that he put up for the cameras while he was mistreating people behind the scenes.

Kanye West isn't one to shy away from controversy, and this appearance on TMZ was among his more egregious media stunts. After talking about his views on Trump, the rapper makes a particularly tone deaf comment about Black Americans and the country’s past treatment of them. He chooses to avoid factual statements in an answer that completely minimizes the horrendous history and places the blame on those who were oppressed. The artist reaches a particular low point with this ignorant statement, receiving considerable pushback from a TMZ staff member. No stranger to making a scene, the rapper manages to outdo himself in this highly-charged interview.