6. Draw! (1984)

This late-career Western offers a fresh take on the aging outlaw trope. Douglas plays Harry Holland, a former gunslinger trying to cash in his poker winnings but ending up in a deadly shootout. Injured and on the run, he takes an actress hostage, leading to a standoff with ex-sheriff Sam Starred. The film’s humor, suspense, and layered character dynamics make it a standout. Douglas shines as the weary but sharp-witted outlaw, proving his enduring screen presence.