Calling Humphrey Bogart iconic would be an understatement, because he really was one of the most legendary figures from Hollywood’s Golden Age. As an actor, his blend of charm, intensity, and cool as an actor continues to feel timeless, and helping this feeling is the fact that Bogart also happened to star in some of the best movies of all time. Many were good back in the 1930s, ‘40s, and ‘50s, and remain compelling to watch to this day.

The following movies demonstrate this exceedingly well, as all rank among his best movies outright, but extra consideration is taken regarding how easy they are to revisit. Fittingly, the following films are Humphrey Bogart’s most rewatchable, ranked roughly – and somewhat subjectively – by how many times fans of his are likely to return to such films, and discover new things about them, hopefully with every watch.

10 'All Through the Night' (1942)

Director: Vincent Sherman

There aren’t too many Humphrey Bogart movies where the actor doesn’t appear to be some shade of cool, but he’s particularly charismatic in the fun and kind of under-appreciated All Through the Night. It’s a comedic crime movie that also bleeds into the war genre, taking place during World War II and following a group of gamblers becoming unlikely heroes when they come across a plan by Nazi Germany that involves the intended destruction of a U.S. battleship.

So it’s Bogart and some other charismatic figures taking on some Nazis, all with a breezy and surprisingly humorous tone, and extremely quick pacing for a film of its age. All Through the Night feels like it might’ve been intended to be wartime propaganda, to some extent, but it’s simple and satisfying and fun, featuring something of a gangsters vs. Nazis storyline that feels rather unique, not to mention entertaining.

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9 'The Petrified Forest' (1936)

Director: Archie Mayo

Speaking of underrated Humphrey Bogart movies, The Petrified Forest is another that doesn’t always get brought up when it comes to the task of selecting the actor’s best films. It’s noteworthy for representing Bogart in full-on villain mode, with Leslie Howard and Bette Davis playing the film’s main characters: two people stuck in a diner that Bogart’s character – plus his gang – have taken over, holding the people there hostage.

Clocking in at a tight 82 minutes, The Petrified Forest flies by pretty fast, and its brevity and consistent tension (thanks to the premise) throughout make it an easy one to rewatch. It’s fun to go back and see it after watching more Bogart movies where he plays the protagonist or fills in a kind of anti-hero role, too, because a villainous turn like this helps demonstrate his not-always-appreciated range as an actor.

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8 'High Sierra' (1941)

Director: Raoul Walsh

A few years on from The Petrified Forest, Humphrey Bogart once again found himself in a film where he orchestrated an ambitious robbery in a somewhat remote location… but here, in High Sierra, he was more of a lead actor, with things mostly being from his perspective. Billed just above him is Ida Lupino, playing a dancer who gets wrapped up with Bogart’s character as he plans a jewel heist in a small resort town.

High Sierra is slick and well-made, as far as classic gangster movies go. It was another key film in Bogart’s overall continual rise in popularity, which began in the 1930s and then was solidified by the early 1940s. It wasn’t so much a breakout role but simply another great one for the actor, and when watched (or rewatched) today, High Sierra is still quite a blast for much of its runtime.

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7 'Key Largo' (1948)

Director: John Huston

One of several movies directed by John Huston that starred Humphrey Bogart, Key Largo depicts a tense hostage situation, a little like The Petrified Forest… only here, Bogart’s character isn’t the one doing the hostage-taking. Instead, the main antagonist is played by Edward G. Robinson, while Bogart’s character and some others – including a young woman played by Lauren Bacall – play the hostages.

Most of the action in Key Largo is contained to a hotel, with poor weather being the excuse for characters to stay within one confined location. This naturally leads to a particularly high level of suspense being built up, and it’s that continual tension and a dynamite cast that makes the film particularly easy to watch, even for those who might not tend to enjoy crime/thriller movies that are multiple decades old.

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6 'The Roaring Twenties' (1939)

Director: Raoul Walsh

Another 1930s Humphrey Bogart that sees him playing second-fiddle to another actor, it’s hard to complain too much in the case of The Roaring Twenties, because the other actor is the comparably awesome James Cagney. The two play men who get wrapped up in bootlegging liquor during the 1920s, finding success at first, but then going through a typical rise-and-fall act, ensuring the good times can’t last forever.

The Roaring Twenties tells the kind of friends-to-enemies story that’s been done before, but there’s an efficiency to the way it’s told here that really works, making it one of the very best movies of the 1930s. As such, it’s naturally an easy one to recommend, both for people who have yet to watch it and for those who might’ve seen it already, but would benefit from doing so again.

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5 'In a Lonely Place' (1950)

Director: Nicholas Ray

In a Lonely Place is right on the cusp of being an underrated film noir from the 1950s, but still has a decent enough number of people aware of its existence. It’s on the line, so to speak, which can be a lonely place for a movie In a Lonely Place, the narrative of which revolves around an actress beginning to suspect her boyfriend has done some terrible things, potentially even including murder.

Keeping the mystery alive while also having something of a tense love story at its core, In a Lonely Place certainly feels unique, and it ends up doing a great deal in just 94 minutes. It contains one of the best performances Bogart ever gave, and his co-star, Gloria Grahame, is also great, with both conveying feelings of suspicion, desire, and anxiety throughout a twisty plot that’s always barreling forward.

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4 'The Maltese Falcon' (1941)

Director: John Huston

One of the best movies of the 1940s, The Maltese Falcon is also extremely complex and twisty, even by film noir standards. What starts simple gets complicated very quickly, with Humphrey Bogart playing a private detective taking on an extremely complicated case that involves one valuable statue, and various shady/unusual individuals who all seem keen to obtain it.

More and more elements get added as The Maltese Falcon goes on, and it’s kind of head-spinning trying to keep up with it all the first time around. Thankfully, movies can be rewatched easier than ever with today’s technology (no waiting for new theatrical releases or reruns on TV), and, if anything, The Maltese Falcon might well be the kind of movie that demands a second viewing to make sense of it all. It’s not the only Bogart movie where such a thing can be said, either…

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3 'The Big Sleep' (1946)

Director: Howard Hawks

The Big Sleep is even more of a trip than The Maltese Falcon, having a similar kind of labyrinthine structure and storytelling style that, by design, is very hard to get a handle on as a viewer. The case taken on by Philip Marlowe (a private investigator) seems contained to a young woman (Lauren Bacall) needing to be followed, at first, but what starts as small balloons and becomes something inconceivably large and complicated as the film goes along.

Even with repeated viewings, some still might come away from The Big Sleep feeling confused, and, at a point, rewatches might be futile. But there is a likelihood of getting a better understanding from going back to a movie as complex as The Big Sleep. Maybe, like a David Lynch film, you won’t ever “get” everything, but certain pieces will fall into place, and a third or fourth viewing may be a little less overwhelming than the first. You always remember your first time (watching The Big Sleep).

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2 'The Treasure of the Sierra Madre' (1948)

Director: John Huston

A movie that was very successful at the Oscars for a Western, The Treasure of the Sierra Madre is perhaps the best collaboration made between John Huston as director and Humphrey Bogart as actor. But it’s more than just a Western, given it also functions as a dark, character-focused drama/adventure movie, all revolving around a desperate search for gold in Mexico during the 1920s.

It serves as an exploration of greed, and the way people are likely to turn on or hurt each other when great quantities of wealth are at stake. The themes and overall message of The Treasure of the Sierra Madre prove bleak, but the movie is also engrossing and easy to return to, not to mention the fact that much of what it has to say is universal, and still applies to this day, in some ways.

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1 'Casablanca' (1942)

Director: Michael Curtiz

It’s hard to go past Casablanca, when ranked by just about any metric. It’s a Best Picture winner, and one of the best of the Best; certainly, it ranks particularly high when considering the war movies that have won the top prize at the Academy Awards. It’s expertly written and extremely emotional, as well as very funny and exciting in parts, arguably feeling perfect from a technical perspective.

And that’s before getting to the characters and all the actors involved, all of them iconic. Humphrey Bogart does carry much of the movie, being its lead, the charismatic, flawed, yet eventually heroic Rick Blaine. Casablanca soars as a war movie, a drama, a romance, and something of a comedy – at least at times – with an eccentric and large cast. It’s got something to offer for anybody in any mood, and appreciation for it just grows and grows the more one takes the time to revisit it.

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