Once when he was a little boy in England, Leslie Hope (He later renamed himself Bob after a race car driver he idolized) wanted to pick an apple off a tree. Symbolic of his career, he didn't want just any apple but highest one possible. He lost his balance, fell and permanently changed shape of his nose.

His big break in Hollywood was getting part Jack Benny turned down in Paramount film "The Big Broadcast Of 1938". The director Mitchell Leisen could not stand star of film, ornery WC Fields, who would run off movie set and come back too soused to do required scenes, flub his lines and scream for his lawyer. Liesen found Hope much more cooperative, although he was a nervous ham in front of camera. Desperate to be a more traditional leading man like Fred Macmurray, Hope begged Paramount to pay for a nose job but they refused. It was in this film he got to sing "Thanks For The Memories" which along with his ski nose became Hope's trademarks.

For his radio show when Hope found out that Jack Benny hired two writers for $1,000 a week, he in turn hired ten writers for $100 a week each and hated paying. At times he would gather staff at bottom of a stairwell and toss their paychecks down as paper airplanes. Other times Hope would interrupt his scribes intimacy with their wives by calling their houses very late at night to go over new material. For their part, writers created Hope movie character, egomaniacal, womanizing and cowardly, all but last trait were true.

Hope's relationship with Bing Crosby was love-hate. In one of their early road movies Paramount Studios filmed two endings in which each of boys ended up with Dorothy Lamour, to see which result audiences preferred. They overwhelmingly chose Bing which annoyed Hope, who got his costar back by constantly reminding him that he wore a toupee. In one scene both had to lie on same bed together (innocently, they were resting) and Bing refused to take his hat off. No amount of coaxing from Paramount executives could get Crosby to change his mind, he did not want to hear Bob's toupee barbs. Hope later said greatest acting performance he ever gave was smiling when Bing won his academy award for Going My Way (1944).