The final Friday Late Show of David Letterman's career began with the unusual sight of not one but two men doing "the run" across the back of the stage. Seconds later, the camera revealed the pair to be Dave and George Clooney, still cuffed together from their Thursday night encounter.
Of course, the show shoots its Friday episodes on Thursdays, so the two hadn't really been shackled together for 24 hours — but the effect was hilarious just the same. So, too, were Paul Shaffer's fumbling attempts to separate the two with the help of a large bolt cutter, which had Clooney musing about the possibility of playing Captain Hook for his next film role. The bandleader finally succeeded, causing Letterman to exult "We're free! We're free, everybody!" and Clooney to make an awkward and hurried exit; perhaps a farewell hug would have seemed superfluous after a couple of hours spent together in bondage.
"Oprah is on the show tonight," Dave informed the audience, who responded with loud cheers. "Not that Oprah," he joked, though indeed it was that all-powerful celebrity mogul, there to counsel him on his impending retirement. With their infamous 16-year feud having long been buried, there was no trace of the prickliness or discomfort that the two stars had once felt in each others' presence; their conversation was warm and spirited, and went to some rather unexpected places.
At Oprah's prompting, Dave revealed that the only souvenir he's taking with him from the show is a crappy rubber sink stopper with a knotted chain. "Wow," said Oprah — because, really, what else could one say to that?
After asking his guest about her work in Africa, Dave threw her a curve. "What do you think about smokin' weed?" he asked. "Are you smokin'?" Oprah said she quit 30 years ago, and the two shared the incidents that caused them to give up the puffin' stuff — the time Dave took down two pints of ice cream without even closing the freezer door, and the time Oprah fell asleep in bed while eating Oreo cookies. "It makes you feel dumb, smoking the weed, you know?" added Dave, helpfully.
After discussing the "Selfie Hell" that Oprah often experiences in public, Dave took one of the two of them — or rather, he tried, before Oprah took control of the situation and snapped the shot with his camera. Their parting was sweet and affectionate, with Dave giving Oprah a tender peck on the cheek. But the emotional high point of the show turned out to be the appearance by comedian Norm MacDonald, who'd made his standup debut on the show back in 1990.
Though MacDonald started his routine with some wry quips — "I don't wanna brag, or anything, but me and Oprah are making the same money tonight" — he jettisoned his usual cynical perspective to pay a heartfelt tribute to Dave, even repeating a garbage truck joke he'd heard from the host when he was 13 years old.
"Mr. Letterman is not for the mawkish, and he has no truck for the sentimental," the comedian concluded, who choked up several times during his routine. "If something is true, it is not sentimental. And I say in truth, I love you."
Dave came over to thank him, and almost seemed to be comforting the teary-eyed MacDonald as the credits rolled. "Very funny, Norm, and thank you for everything," he said. "That was very sweet, Norm!" It was, indeed.