In the wake of the public's recent reexamination of the questionable ways the media used to treat and talk about high profile women in the 2000s and early 2010s, the internet has been digging up old, problematic interviews, tabloid covers and press appearances.

From Lindsay Lohan's frustrated 2013 appearance on David Letterman's Late Show, in which the talk show host made light of her mental health struggles, to Britney Spears' upsetting 2003 chat with Diane Sawyer, who shamed the pop star and pushed her to tears amid already overwhelming public scrutiny, it's clear the media's treatment of celebrity women in the 21st century has been, for lack of a more eloquent phrase, pretty damn messed up.

One of the most infuriating examples of the harsh and unforgiving way post-Y2K media treated its female stars took place in 2007, when Paris Hilton, fresh off serving jail time for a probation violation following a reckless driving charge, sat down with Letterman—a repeat offender, it turns out—to promote her latest perfume and new film, Repo! The Genetic Opera.

Unfortunately, those were apparently not the topics the Late Show host found most interesting, as Letterman opted instead to intimately grill Hilton, about 26 at the time, about her arrest and time in jail (subjects not cleared ahead of time), despite her clear discomfort.

During the chat, Letterman mercilessly asked Hilton question after question about her time in jail, spending nearly seven minutes—most of their time together—bringing up her stint in jail and not the items Hilton had specifically come onto the show to talk about, even after Hilton repeatedly asked him to move on from the topic.

Laughing and making sarcastic remarks through most of the chat, making it clear he found Hilton's misfortune humorous, Letterman even asked Hilton to reveal what each of her meals were like when she served time, forcing her to relive the experience with a play-by-play breakdown of her time spent at the Century Regional Detention Facility in Los Angeles. He also bizarrely asked her if she lost weight during her time there.

"Wasn't that horrible?" he asked Hilton at one point, referring to her experience behind bars.

"Obviously it was a very traumatic experience," she said of the experience, making it clear it was a difficult topic for her to talk about.

Over the course of their increasingly uncomfortable conversation, Letterman, who refused to move onto any other topics for the majority of Hilton's appearance, condescended to her about the law and even asked her if she was aware why she went to jail.

Paris Hilton The Late Show With David Letterman 2007 Interview
Ray Tamarra, Getty Images

Even after Hilton became visibly emotional and welled up with tears, making it clear that she didn't want to answer any more intimate questions about the challenging and embarrassing experience, Letterman simply wouldn't relent—until the last two or three minutes, when he finally allowed Hilton to speak about her new perfume and upcoming film.

Even when discussing her Can Can by Paris Hilton perfume, however, the talk show host turned the segment into a joke, spraying the liquid on his tongue and touching Hilton without her permission to dab the fragrance on her neck.

Letterman did eventually apologize for his behavior. In 2008, Hilton appeared on the Late Show again to promote another film, during which Letterman admitted, "I made a fool of myself and I hurt the woman's feelings. I went too far."

"In 26 years of being on the air, I have offended thousands of people... but Paris, God bless her, has the backbone to come and be on the show," Letterman added.

Though Hilton handled the whole ordeal gracefully, watching the clip back fourteen years later paints a whole new picture about how unforgiving and harmful the entertainment media was to famous women not so long ago. Yes, we should hold our celebrities accountable—but while Hilton served her time and took accountability, that doesn't mean she should have been publicly humiliated and traumatized further in front of a live studio audience.

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