It takes nerves of cold steel to anchor as much live television as Regis Philbin did in his long career. Now, following his death on Saturday, fans are celebrating Philbin’s trademark unflappability by recirculating an old episode of Who Wants To Be A Millionaire that finds the host deftly navigating the high-stakes drama of a million dollar question as he terrorizes celebrity contestant Norm Macdonald, who’s usually the one doing the terrorizing.
After an introduction in which Philbin pats Macdonald’s head as if he were a child, he pokes and prods until the comedian’s poker face, so rarely torn asunder, collapses into a vortex of anxiety. Having used up his last lifeline, Macdonald approaches the final question—Which golf course has a Cold War-era bunker beneath it?—with trepidation. He’s as riled up as we’ve ever seen him, spurred on no doubt by the high stakes—he’s playing for Paul Newman’s Hole in the Wall Gang Camp—but also by Philbin’s straight-faced probing. “You got a little gambling streak in you, don’t you?” Philbin asks, knowing full well that Macdonald does. “You wanna see if you can beat the game, don’t you? You wanna win a million dollars, don’t you?” The audience is on the edge of their seat. Macdonald is squirming, hopping between two answers
Unable to potentially sacrifice the half a million he’s already raised for the camp, Macdonald eventually buckles under Philbin’s ribbing, only for the host to dramatically reveal that Macdonald’s shaky guess was the correct one. It’s not only great TV, but further evidence that Philbin could keep up with (and sometimes shake up) the best comedians in show business. Macdonald clearly revered him, too. In a 2017 tweet, he said that he was still hoping to work with the host one day. “[S]till the best,” he wrote.
Watch Macdonald’s full game in its entirety below. You can jump ahead to 24:30 for the final question, or start from the beginning to learn that he and Kato Kaelin had been friends for 15 years by that point.
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