"Pretty sweater. Keep bending over like that," Matt Lauer tells his Today co-host Meredith Vieira. "It's a nice view."
That off-air comment, captured by cameras in 2006, is one of the uncomfortable moments in what amounts to an excruciatingly awkward highlight reel that has been circulating over social media since Wednesday.
That was when Lauer met his sudden downfall as NBC fired him for inappropriate sexual behaviour.
Some of the clips are merely a little cringe-worthy given the hindsight of subsequent events; others more disturbing.
In the latter category is Lauer's less-than-tasteful - some would say nasty and patronising - questioning of actress Anne Hathaway in 2012 after paparazzi had taken a revealing photo up her skirt as she exited a car.
"Seen a lot of you lately," he wisecracked. Saying "Let's just get it out of the way", Lauer forced her to respond and tell him what "lesson" she had learned.
Hathaway was lauded for her restrained answer, in which she segued smoothly to her character in Les Miserables, the film she was there to promote.
In a much more high-stakes encounter in 2016, during the election, Lauer was criticised for interrupting candidate Hillary Clinton repeatedly and grilling her on a personal email issue - asking if it was a disqualifying factor in her presidential quest.
He was much less challenging of her opponent, Donald Trump. Lauer was accused not only of a lack of preparation but, by some, of sexism.
"I was almost physically sick," Mrs Clinton later wrote in her memoir What Happened.
Then there was Lauer's 2014 interview with the first female chief executive of General Motors, Mary Barra.
After mentioning her significant qualifications, he asked: "There are some people who are speculating that you also got this job as a woman, and as a mom, because people within General Motors knew this company was in for a very tough time, and as a woman and a mom you could present a softer face and softer image for this company as it goes through this horrible episode.
"Does it make sense or does it make you bristle?"
Ms Barra responded firmly that she was "selected for this job based on my qualifications".
But Lauer was not finished: He then mentioned Ms Barra's children and asked if she could handle the dual pressures of motherhood and being a chief executive.
"Can you do both well?" he asked - a question, many noted, that is never asked of a male boss.
Lauer said later that she had previously raised the issue, so it was fair game.
Lauer's relationship with co-host Ann Curry, rumored to have been strained at best, seemed on display the morning she bade a tearful goodbye to Today fans after being forced out of her position beside Lauer - whom many viewers blamed for her departure.
As she wept, Lauer leaned in to kiss her, but she appears to move away - resulting in an awkward kiss on the side of her head.
Also circulating have been several comedy bits on Today that now seem somewhat ill-advised.
In one - an installment of Today! The Musical - a staff member spills a drink onto Lauer's designer trousers.
He removes them, and stands in his boxer shorts as his female co-hosts enter the room.
"Drink it in, ladies!" he says. "Get it while it lasts!"
Then there's the comic sketch the show did in 2012, unearthed on Wednesday by The Daily Show, which seems to many to mock sexual harassment.
In the sketch, Lauer is apparently "smacked on the tush" by Willie Geist.
"It has everyone around here talking and accusing," notes Savannah Guthrie.
Lauer pretends to be traumatised. Asked whether he provoked it, he replies: "I didn't do anything differently. I wasn't wearing a different cologne."
Then, he says the worst thing is that since the alleged smack on the bum "he hasn't called, he hasn't written".
"This kind of thing happens all the time," notes investigative correspondent Jeff Rossen. "But is it really appropriate for the workplace?"