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Raoul Walsh directed several gangster films, but High Sierra wasn't another drop in the bucket.
Rather, its main character, Mad Dog Earle, was a nuanced man unlike most of the criminals depicted in movies before him. Making him even more unique was the way in which Humphrey Bogart brought this layered man to life in 1941.
1. Lupino was the bigger star.
Before Sierra, Humphrey Bogart and Ida Lupino worked together in They Drive By Night, which was also directed by Raoul Walsh. In that film noir, Lupino got her chance to shine in a showstopping courtroom confession. Her wide-eyed hysterics were can't-miss cinema, and Hollywood was in love with her performance (read about that here). As a result, Lupino received top billing in High Sierra and $800 thousand more than Bogie. Despite this, it wasn’t a competition between the leads, and they worked together one last time in Thank Your Lucky Stars.
2. A stuntman shot himself. Sorta.
Buster Wiles was an experienced stuntman who worked in Hollywood for approximately twenty years. In High Sierra, he doubled for Bogie and performed Mad Dog's death scene in which he tumbled down a mountain after being shot. Interestingly, Wiles also played the officer who fired the gun. As Wiles jokingly put it: “I shot myself off the mountain.”
3. Bogie helped Ida cry.
While filming an emotional scene for Sierra, Lupino couldn't get herself to cry on camera. So Bogie said, “If you can’t cry, just remember one thing: I’m going to take this picture away from you.” The joke loosened her up. She then took his advice and thought about a time when she had to say an emotional goodbye. In no time, the tears were flowing! Remembering her co-star, she said, “He was the most loyal, wonderful guy in the world.”