The war horse of American late-night TV, David Letterman, has announced his retirement.
2015 will be the final time we hear musical director Paul Shaffer's sycophantic laugh, as his boss has decided to hang it up for good.
Letterman may not be built for the viral era of late-night TV — none of his recent bits have had the traction of a Jimmy Fallon or Jimmy Kimmel clip — but there is one area where Letterman will always remain supreme: The awkward celebrity interview.
Letterman has often given off the impression that he's too smart (and too bored) to bother interviewing celebs, despite the fact that this makes up a solid 90 percent of his job. Younger viewers might think this is linked to old age or senility, but no — Letterman has always been like this.
Craig Ferguson might ask his guests to share an awkward pause with him, but he merely adopted the awkwardness. Letterman was born in it, molded by it.
In honour of the patron saint of listicles, here are Letterman's Top Ten awkward moments.
Lindsay Lohan (2013)
Perhaps Letterman's crowning moment of uncomfortable, this interview was ostensibly done to promote 'Scary Movie 5', but ended with Letterman asking questions like, "Aren't you supposed to be in rehab now?" "Did Charlie Sheen loan you money?" "Yes or no, do you steal stuff?" When it was over, Letterman praised her for having "enough spine, enough poise" to appear on the show, but Lohan was already in tears.
Paris Hilton (2007)
"How'd you like being in jail?" Hilton thought she was on the show to promote her new perfume, but Letterman had other ideas, peppering her with detailed questions about her stint in jail. Hilton begged Letterman to change the topic, which is the worst possible thing she could have done — that's like throwing a cutter into a shark tank.
Joaquin Phoenix (2010)
"What can you tell us about your days with the Unabomber?" Phoenix appeared on Letterman's show at the height of his 'I'm Still Here' phase, pretending to be in the middle of a drug-fueled meltdown in the name of performance art. He barely spoke to Letterman at all, which just gave the deadpan late-night host more room to do what he does best.
Drew Barrymore (1995)
Barrymore came bounding on stage with flowers for Letterman on his birthday (and without a bra), before telling a story about a recent appearance at a club where she'd stripped off for a "performance piece". She then jumped up on Letterman's desk with her back to the crowd and gave him a full-frontal flash. Unphased, Letterman asked for the details of the club.
Courtney Love (2004)
Letterman seemed to enjoy Barrymore's performance as much as the next guy, but he wasn't so entranced by Love. The Hole frontwoman and amateur detective bared her chest to the audience multiple times, leading Letterman to drolly ask: "What is the nature of your life these days?"
Harvey Pekar (1987)
The comic book author's appearances on Letterman's show were so awkward that they basically made a movie about them ('American Splendour'), but after eight increasingly bizarre appearances, he was finally banned from the show for criticising General Electric (which, as any '30 Rock' fan will recall, used to own NBC).
Crispin Glover (1987)
Oh, man. Remember when we said the Lindsay Lohan interview was the most uncomfortable? Nope. It was this one, when legendary Hollywood weirdo Crispin Glover appeared in character (without warning anyone) to promote his role in 'Rubin & Ed' and ended up almost kicking Letterman in the face.
Andy Kaufman & Jerry Lawler (1982)
Glover's appearance wasn't the first time a Letterman interview devolved into physical violence — that honour belonged to wrestler Jerry Lawler and comedian Andy Kaufman's joint appearance in '82. The two were in the middle of a staged feud that culminated in Lawler slapping Kaufman and Kaufman retaliating with a sweary tirade; Letterman, at the centre of the madness, claims to have no idea what was going on (his on-air reaction would seem to back this up).
Harmony Korine (1998)
The 'Spring Breakers' director was awkward enough during his interview that you could understand why he'd never been invited back on the show, but the real reason for his ban is even juicier — years later, Letterman revealed that Korine had been caught rummaging through Meryl Streep's purse backstage.
Madonna (1994)
"Aren't you going to smell them? I gave him my underpants and he won't smell them." So, yeah, that's a thing that happened on network television.
