High Sierra

This depression era heist film is one of Humphrey Bogart's breakout roles that made him a star, along with The Maltese Falcon.

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, a dancehall girl from Los Angeles.

Tropes used in High Sierra include:

Badass in a Nice Suit
Climbing Climax: Earle flees the police up the rocky slopes of the titular High Sierra
Downer Ending: 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.
Film Noir: This is a classic example
The Caper: Roy, Babe, and Red rob a resort hotel
One Last Job: Roy wants to retire after this heist