Video excerpts of the uncomfortable interview were uploaded over the weekend by a Twitter user named Trey Taylor, with the caption: "This Lindsay Lohan interview on David Letterman in 2013 is horrifying to watch now."
The new posts have set off a new wave of backlash over the thoughtless comments made by Letterman at the time.
The clips shared by Taylor show Letterman relentlessly badgering Lohan, asking repeated questions like "How long will you be in rehab?" "How many times have you been in rehab?" and "How will this time be different?"
At the time Lohan was scheduled to complete 90 days of court-ordered rehab in bid to avoid jail time over charges relating to a car accident the year before.
Trying to keep her cool under the barrage of inappropriate questions, Lohan reminded Letterman that the topic of her rehab was supposed to be off limits.
"We didn't discuss this in the pre-interview, just saying," remarked Lohan. She also desperately tried to steer the conversation to easier topics.
"We're here for a movie," Lohan pleaded. "Let's stay on the positive."
In an effort to take control of the interview, Lohan snatched Letterman's notes and rebuked him for his topic choice.
"You can't make a joke of it, that's so mean," she said. "No, you're not doing that. We're not doing that. No, it's my show now."
Lohan was eventually brought to tears by Letterman and the highly insensitive line of questioning has been outraging Twitter users over the past few days.
"Ugh this makes me so sad. Shame on David Letterman and shame on his show for the claps and laughs throughout the interview," one Twitter user wrote.
"This is vile on so many levels," commented another using, continuing, "The misogyny. The blindsiding. The stigma of addiction & rehab. The hypocrisy of wanting people to recover, but then judging how they choose do so".
"This is awful like how can he not read that it's super uncomfortable and should stop???," wrote another.
Some commenters posted other clips in which Letterman is seen to be making his female guests noticeably uncomfortable, including a clip in which he pushes Janet Jackson to address the Super Bowl "nipplegate" controversy and another in which he insinuates some very lewd things in relation to Christina Aguilera's piercings in "special areas".
Just a few Twitter users struggled to see the problem with Letterman's questioning and laid the blame at Lohan's door.
"He wasn't giving her the star treatment because she wasn't taking rehab seriously and she knew it," was one negative statement.
Another shared an 80s clip in which Cher refuses to kowtow to Letterman and is actually booed by the crowd for calling him an a$$hole.
Letterman has been retired from broadcasting for the past six years. He has openly discussed his own battle with alcohol addiction. Neither he, nor his people, have responded to requests for comment.
