You get the first team-up of John Huston (who wrote the screenplay) and star Humphrey Bogart. They'd reunite many times after this to create classic films, including The Maltese Falcon later that very same year and Treasure of the Sierra Madre in 1948.
Sierra kind of represents the death of the gangster genre. It follows all the conventions of the other Warner Bros. gangster films like Little Caeser, Roaring Twenties or Public Enemy. Most importantly, because of the Hays Code operating in Hollywood at the time, it was considered improper to lionize or celebrate criminality, so all the gangsters in these movies have to face punishment. In most cases they die, sometimes really abruptly, like Edward G. Robinson in Little Caeser. One minute, he's threatening his enemies and posing for photos at a classy banquet in his honor, the next he's lying in a pool of his own blood wondering if this is the end of Rico.
Similarly, High Sierra tells the story of a criminal watching his life unravel before his eyes. Bogart plays Roy Earle, recently released following a stint in the big house for armed robbery. He'd been sentenced to life, but won an early release following a series of bribes by his old boss, Big Mac (Donald MacBride). Of course, freedom comes with a price, and Big Mac expects Earle to begin work immediately on a new caper along with two fresh-faced crime newbies.
All of this material comes off swimmingly. Bogart had been playing nogoodnicks like Earle for the majority of his career at this point, and he speaks Huston's stylized tough-guy dialogue with just the right mixture of menace and apathy. There's a certain thrill in hearing Bogie scream "Come and get me, coppers!" from his craggy hideout atop Mt. Whitney that's undeniable.
Bogart notably brings a good deal of melancholy to the role, a buried sadness that would become his trademark in films like Casablanca, To Have and Have Not and Dark Passage. Unlike Edward G. Robinson's Rico, who relishes violent criminality, Roy Earle wants only to meet a nice girl and settle down. He even proposes marriage to simple farm girl Velma (Joan Leslie) as a way of escaping his life outside the law, though he's soon enough rejected and sent into the arms of gun moll Marie (Ida Lupino). Perhaps this is why High Sierra is often seen as the death knell of the gangster movie. After this, the gangsters got all depressed, finding the weight of the world bearing down on them, and the genre morphed into film noir.
Actually, now that I think about it, with their next feature The Maltese Falcon, Huston and Bogart essentially created American film noir.
I've been going on and on about his considerable gifts (Huston certainly ranks among my favorite directors), but it was actually legendary director Raoul Walsh who brought his talents to High Sierra. As he did with other notable gangster titles like Roaring Twenties (also featuring Bogart) and White Heat, Walsh overloads the movie with camera tricks and small flourishes, giving it a modern feel other films of the era decidedly lack. In particular, the car chase near conclusion in High Sierra is executed with remarkable flair.
Regrettably, it's not all good news on the High Sierra front. In many ways, the film has aged badly. One character in particular requires mention in any honest review of the film, and that's Willie Best as Algernon. He's the caretaker/handiman for the High Sierra cabin used by Roy Earle and his crew as a hideout, and he happens to be black. And because this was 1941, he's an egregious, embarrassing, ridiculous racial stereotype that threatens to completely derail the movie every time he's on screen. I suppose his antics, like going crosseyed and falling asleep all the time, were considered hilarious upon the release of High Sierra, but now they're beyond offensive. This sort of minstrel, jigaboo stereotype tarnishes so many classic films, but High Sierra is one of the most egregious examples I have ever seen. It's shameful, really.
And this isn't the film's only major misstep. Far too much time is devoted to the family of Velma, the object of Roy's affections. Much of the actual planning and execution of the robbery at the center of the film's plot is left out of the film to make room for endless sequences in which Roy visits Velma's poor family, pays for an operation on her club foot, and eventually meets with the other man whom she agrees to marry.
It's a plot thread crucial to the success of High Sierra's story, for sure. We need to see that Roy sees Velma as an escape, not just from his lifestyle but from himself. In her eyes, and the eyes of her family, he's a dignified, respectable older man. For a guy known in the newspapers as Roy "Mad Dog" Earle, who's hounded by police whenever he shows his face in public, being treated kindly and without suspicion seems like heaven on Earth.
But we understand this concept by the second scene featuring Velma and her grandparents. It didn't require making them main characters.
There's a lot to recommend in High Sierra, from the stark black and white photography to the sharply written dialogue. And the final showdown between Roy and the cops on Mt. Whitney's one of the defining moments in all of gangster-dom. But the other titles released recently by Warner's in the Gangster Box Set, incluidng Public Enemy, Angels with Dirty Faces, Little Caeser and Roaring Twenties outpace it by about a country mile. Those are the classics, this is an interesting transitional moment in film history. All are important, but some are just more entertaining than others.
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