It was in Hollywood, hick town or no, that he got paired with Bing Crosby, a much bigger star, in a small buddy comedy called “The Road to Singapore” (1940). This was the first of the series of “Road” movies—“The Road to Morocco,” “The Road to Utopia,” “The Road to Rio”—which made him a household name, and are his best shot at posterity. They really are funny, and curiously modern, and a key part of this, strange to say, is Hope’s sex appeal. He’s a self-confident wise guy—exposed as a coward but not as a nebbish. Riding the back of a camel with Crosby in “Road to Morocco,” he’s as at ease in his undershirt as Brando.
Zoglin is right that the meta-comedy, “the fourth-wall-breaking,” of those movies is still charming, and must have seemed startling at the time. After Hope stops to recapitulate the plot in “Morocco,” Crosby protests that he knows all that. “Yeah, but the people who came in the middle of the picture don’t,” Hope replies. This is a stunt, and we buy it because the characters are so companionable—the real subject of the movies was Bob and Bing’s friendship, and our sense that, as with Redford and Newman later on, they were funny, attractive equals. Crosby isn’t truly a straight man; Hope isn’t truly a clown. The Hope character doesn’t see himself as ineligible for Dorothy Lamour, just squeezed out.
The simulation of that brotherly relationship turns out to be an artistic invention of the movies. In truth, the two men barely tolerated each other. “He was a son of a bitch,” Hope remarked after Crosby’s death. Hope’s brand of sullen and Crosby’s brand of sullen were different: Hope’s outwardly genial and inwardly inert, Crosby’s fuelled by alcohol and anger, and perhaps by enough intelligence to make this great jazz singer, once described as the “first hip white person in America,” think that he was wasting his talent on these matters [...]
For a decade, from 1939 to 1950, Hope was consistently and even irresistibly funny, in a way now hard to analyze, since its later inferior, mechanical TV version is so close to it in style. Part of it is period parody. Hope is to the tough guys and hardboiled dicks of the forties what Woody Allen was to the smooth seducers of the sixties—at once boldly aspiring and obviously inadequate. “It only took brains, courage, and a gun,” Hope announces in his 1947 parody film noir, “My Favorite Brunette.” “And I had the gun.” We know that’s not a Groucho line, typically an overwrought boast that dissolves into wordplay. (“One morning I shot an elephant in my pajamas. How he got into my pajamas I don’t know.”) The key is the feint at courage, and the rueful confession of inadequacy. (As with his simple statement in “The Road to Zanzibar,” as he leads Crosby into the unknown: “Oh, come on, you follow me. In front.”)
- Adam Gopnik, 'Laugh Factory', New Yorker, 17 November 2014