When Bob went out to Hollywood in 1937, he got friendly again with Crosby on the Paramount lot and they became good friends. They entertained together at [the] Del Mar racetrack, where Bing was a part owner and Paramount executives saw their act onstage together and said, "Hey, these guys might work together in a movie."
So they geared up a movie that ended up being called Road to Singapore. This came out in early 1940 and it was just terrific. It was the highest-grossing film for 1940 in a year with a lot of big Hollywood films, and the audience responded instantly to the chemistry of the two of them on-screen together. They were relaxed, informal — they seemed to be friends authentically, not just movie characters. The movie was so much fun that it launched a series.
They were friends and they loved working together, but they were not close friends. They were very different personality types. ... Bob was someone who loved being famous and loved being out there as a star and he loved talking to fans and he was basically a happy guy. Bing was much more ambivalent about his stardom, I think. He was more reclusive. He didn't like the Hollywood scene; he moved up to Northern California halfway through his career. He didn't like showing up at things. There was a famous Friars Club Roast for Bob Hope in the late '40s and every major comedy star — from Milton Berle, George Jessel, etc. — were there. ... And [Bing] didn't show up. I think that bothered Bob a little bit.
I think there was a slight bit of resentment there. I think also Bob envied Bing in the early years, particularly. Bing was more successful and Bing was a smart businessman. Bob learned a lot from him. I think that there was a little bit of a rivalry. Like so many movie pairings, they were great on the screen but offscreen it might have been another story. They were friendly, but when Bing died in 1977, I do not think Bob Hope was one of his close friends, although Bing's wife Kathryn did invite Bob Hope to his funeral. Bing preferred the friendship of Phil Harris. With Harris, Bing could be himself. With Bob Hope, Bob always needed to have an audience and be "on". Bing did not need that...
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