Why David Letterman's Interview With Lindsay Lohan Went Too Far

At first, it seemed like the internet and celebrity gossip would be natural allies. Where once you had to slog to the store for a tabloid to get your dose of wild celebrity antics, now you could just check your phone to see who's trending on Twitter. But the last few years have seen a shift in how the media treats certain people (and arguably thankfully so) — especially regarding the portrayals of famous women. And the internet has, in some respects, become an unlikely vehicle for accountability, with social media users often the first to point out any transgressors. 

While an offensive comment here and there could once fly under the radar, now celebs are called out on bad behavior, often leading to severe consequences (insert DaBaby anecdote here). Even offenses from the distant past (or in this case, 2013) can come back to haunt you, as David Letterman discovered when an old interview with the once-publicly lambasted Lindsay Lohan resurfaced, per Entertainment Weekly.

Clips of Lohan's appearance on "The Late Show With David Letterman” started doing the rounds on platforms like TikTok and Twitter earlier this year, with many viewers criticizing the host's rude and insensitive treatment of his guest. But, considering the past is the past, why are people upset with Letterman over an interview that's nearly a decade old? And what exactly did he ask that was so offensive?

David Letterman kept pressing Lindsay Lohan

When Lindsay Lohan agreed to an interview with David Letterman in 2013, she clearly expected to talk about her upcoming project, "Scary Movie 5." Instead, Letterman grilled her on just about everything else. The interview started off with friendly, if slightly harsh, banter about Lohan's supposed shoplifting habits, but quickly took a darker turn. "Now, aren't you supposed to be in rehab?" Letterman asked.

The "Mean Girls" star calmly confirmed she would be receiving treatment soon, but became visibly uncomfortable. "What are they rehabbing? What is on their list? What are they going to work on when you walk through the door?" he asked, to the (then) delight of the audience. Retaining her composure, Lohan coolly quipped: "We didn't discuss this in the pre-interview." She added, "I'm happiest when I'm working and healthiest," and I think this is an opportunity to focus on what I love in life." While the segment did end with Letterman commending her bravery, by that time Lohan was clearly trying to hide her tears. As Letterman pressed her on the type of addiction, she replied, "Now you sound like Dr. Phil." Letterman then joked, "Now I'm the one who's having the blackouts." 

The clip started resurfacing, per Ok!, after the release of "Framing Britney Spears," and many social media users were quick to point out that like Britney Spears, Lohan was also treated unfairly, noting that Letterman's continued focus on her rehab visits added to the stigma surrounding addiction.

Lindsay Lohan wasn't the only female celebrity David Letterman made uncomfortable

As David Letterman is probably aware, the internet never forgets. After his disastrous interview with Lindsay Lohan went viral, many more instances of his disrespectful treatment of famous women popped up – as Buzzfeed noted in a recent rundown. From openly objectifying Jennifer Lopez to disregarding Janet Jackson's boundaries to viciously insulting Monica Lewinsky, it seems that Letterman spared little thought towards the negative impact his comments might have caused during a time when such things weren't really thought about twice.

Of course, times change, and people's attitudes and opinions evolve with them. It's highly unlikely that the infamous Lohan interview would go the way it did today. But, just because it's obvious that something was wrong in hindsight doesn't mean it was right back then. 

In another clip from the past that has recently gone viral, Craig Ferguson, former host of "The Late Late Show", actually defended Britney Spears. Despite being filmed in 2007, when female celeb bashing was at a fever pitch, Ferguson now famously announced on-air that he would no longer make jokes about the singer, stating, "We shouldn't be attacking the vulnerable people." If only everyone showed Spears and Lohan that same amount of kindness.