Much like Cary Grant, it’s a little bit jarring to watch a Humphrey Bogart movie where he doesn’t have first billing, strange to contemplate a time before the man was not an icon, when casting him as a lead and not a second-stringer was still considered a risk. With High Sierra, it’s especially perplexing — isn’t this one of his most famous roles? — until you remember the year it was released. 1941. There it is. The year that catapulted Bogart into the stars. 

Repurposed from a canceled John Dillinger project that garnered extraordinarily bad press upon its announcement, High Sierra straddles genres like few classic Hollywood films ever managed to do with success — too sentimental to be noir, too modern to be a Western, too still to be action or gangster or even really crime. If High Sierra is one thing at all, it’s a tragic romance. But even this aspect doesn’t reveal itself until late in its runtime, a surprise as much to Bogart’s preoccupied bank robber as it is to a captivated audience. What makes High Sierra so memorable, then, is that it’s a seamless blend of all those genres, a capital-p Picture that sneaks up on you and holds you tight. 

Happy marriages behind and in front of the camera account for the unexpected success of High Sierra. Behind, the combined talents of one-eyed director Raoul Walsh, best known at this point for movies like The Roaring Twenties (1939) and They Drive By Night (1940), and co-writers John Huston (do I really need to list his credits?) and W.R. Burnett (who wrote the novel upon which the film is based). Sometimes such god-tier combinations prove to work better in theory than in practice; here, Walsh and Huston’s strengths don’t overpower each other but rather amplify what’s best from both of them.

And in front of the camera: The pairing of worn-down Bogart and steely-soft Ida Lupino. Like most leading men of his age and caliber, Bogart is too old for Lupino. But this is one of the rare instances when the difference in age accentuates their commonalities as well as the movie’s themes. It’s almost an afterthought — there was absolutely no chance of an actress older than 30 playing this part (even 25 would be pushing it!) — but a poignant one nonetheless. 

Released from an Indiana prison after an eight-year stint thanks to a corruptly purchased pardon, Roy Earle (Bogart) is sent by his crime-lord boss to California for a hot new caper. For this job, he’ll be the expert veteran to a pair of over-eager punks, the one responsible for making everything go smoothly. Once in California, there’s an immediate wrench in the plan. The two punks have dragged in Marie, a dime-a-dance girl they picked up in L.A., and trusted her with information about the job without Earle’s consent. Initially dismissive and resentful of her presence, Earle soon discovers Marie is worth more than the two of her boyfriends combined. (Yes, boyfriends. It’s not subtle. Maybe the censors were drunk that day!)

Earle insists nothing romantic will happen between the two of them because of his questionable detour into domestic fantasy with a mildly disabled farmer’s granddaughter, who has no interest in him despite his paying for the surgery that fixes her clubfoot. Earle is wrong, of course. After Marie trades volatile polyamory for sympathy and relative safety with Earle, he realizes they are well-matched because they are the same. Despite their differences in age and life experiences, they have both been trapped in inescapable situations and deeply felt the urge to “crash out” at any cost — to be free. 

High Sierra is a story that can only end one way. It’s a testament to everyone involved in this production that the inevitable ending feels uplifting in its tragedy rather than cloying and moralistic. In hindsight, it’s also no wonder this was half of Bogart’s 1941 one-two punch. Here, his screen persona is craggy, tired and urgent, fully formed Bogart, as if no other version of him ever existed. 

Available today, the two-disc Criterion Collection edition of High Sierra is a treasure trove of film history. Certainly worth a purchase for the gorgeous 4K digital restoration of the film itself, the edition also includes Colorado Territory (1949), Walsh’s Western remake of High Sierra starring Joel McCrea and Virginia Mayo, and two documentaries about Walsh and Bogart, respectively. Also notable among the plethora of special features is an interview with film historian Miriam J. Petty about Black actor Willie Best, who has a minor and horribly racist role in the film. This interview gives context to Best’s role and belatedly returns some credit to him as a performer who had no choice but to perpetuate minstrelsy in order to get on screen at all. 

High Sierra is now available from the Criterion Collection on Blu-ray and DVD.