It makes sense that these two would be put on one DVD, being the only times Cathy O'Donnell and Farley Granger were paired in leading roles. Not to mention they're both semi-romantic noirs about criminals on the run. I was planning to watch only the more popular (but unprofitable) TLbN. Fortunately, they're pretty short at 95 and 83 minutes, respectively, so I made time across two nights.
In TLbN, three men escape from prison and team up for bank robberies. Circumstances split Bowie from the others, and despite his less criminal disposition, he develops a bigger reputation. He wants to give up on crime and settle down with his new girlfriend-cum-bride, Keechie, but an old comrade insists he owes them forever. In SS, mail carrier Joe tries to swipe $200 to help his pregnant wife, Ellen, but it turns out to be $30K -- in dirty money, so he's bound to get unwelcome attention from worse than the police.
TLbN is based on the Edward Anderson book Thieves Like Us, which also became a Robert Altman movie by that title. Some see it as a Bonnie and Clyde predecessor, but Keechie isn't really involved in the crimes, nor does she encourage Bowie to keep at them. For his part, Bowie doesn't seem violent, even tho he apparently committed murder at 16. He's also notably baby-faced for 23, which may make the audience more inclined to sympathize with him.
It's hard to see a picture like this as modern in any way, but I notice a few arguable relevancies. News reports consistently mischaracterize Bowie as the ringleader, demonstrating a long-running pattern of untrustworthy media. And in perhaps the most unusual scene, Bowie and Keechie elope at a cheap, fast, somewhat shady service, indicating that the sanctity of marriage had already begun to take a beating in U.S. culture.
In contrast to Bowie, Joe had intended no bigger crime than desperate petty theft, so he almost gets a Hitchcockian level of automatic sympathy. And in contrast to Keechie, Ellen has no idea at first and then wants Joe to turn himself in. Alas, at that point, it's not so simple. He sees fit to commit acts of greater desperation.
I actually wound up preferring SS, and not just because the protagonist is less of a jerk. He gets into quite a web to untangle. I didn't understand everything right away, but I appreciate the thought going into it. Besides, as much I enjoyed Butch Cassidy and the Sundance Kid, stories about crooks stuck in a pattern don't convey plot progression as handily as stories about someone with an overarching crisis to solve soon.
Neither flick has a particularly happy ending, of course, but SS comes closer. If you rent the disc and don't feel like a double feature, I recommend skipping to the second.
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