This 1941 heist film, directed by Creator/RaoulWalsh and co-written by Creator/JohnHuston, is one of Creator/HumphreyBogart's breakout roles that made him a star, along with ''Film/TheMalteseFalcon''.

Bogart stars as robber Roy Earle, pardoned six years into a life sentence through the machinations of ailing crime lord Big Mac. Earle has been broken out to do one last heist, alongside two young toughs, who disgust him with their lack of discipline and smarts. Earle finds himself out of place in a world that is changing fast. His failed romance with a young Dust Bowl refugee convinces him that he has no place in honest life, but when the heist goes bad, he finds loyal companionship in the form of Marie (Ida Lupino), a dancehall girl from Los Angeles.
!! This movie contains examples of:

* BadassInANiceSuit: All the gangsters.
* TheCaper: Roy, Babe, and Red rob a resort hotel
* ClimbingClimax: Earle flees the police up the rocky slopes of the titular High Sierra
* DownerEnding: [[spoiler:Everybody dies except Rodriguez, who talked, and Marie, who's going to prison or possibly an asylum, as she appears to be having a nervous breakdown at the end.]]
* {{Expy}}: Roy Earle is based on John Dillinger.
* FilmNoir: This is a classic example, although one might consider it a gangster film or pre-noir, as many consider the genre to have been defined with ''Film/TheMalteseFalcon''. Historians cite it as a GenreTurningPoint, in that it was when the 30s gangster film became Noir, noting the greater psychological focus and the symbolism (which generally defined noir) separated it from the 30s gangster films, which were more focused on social opinions of urban crime rather than exploring character motivations.
* MeaningfulName: Roy Earle is a reference to Theatre/KingLear, (Earle is a semi-anagrame for Leare, and Roy is French for King). About the only thing in common was the theme of growing old and the longing for OneLastJob.
* NeverGoingBackToPrison: Roy is haunted by BadDreams of prison, and is determined to never return. [[spoiler:Like so many other examples of this trope, he eventually chooses SuicideByCop rather than get taken back to prison.]]
* OneLastJob: Roy wants to retire after this heist
* {{Retirony}}: [[spoiler: He ends up dead]].