Clint Eastwood's 10 Greatest Acting Performances

4. Heartbreak Ridge (1986)

Far more nuanced and suffused with appreciation of American military valor than the other war film that came out that month, Platoon, this character study climaxes with the 1983 invasion of Grenada but it’s really about the psychological burden borne by fighting men as they carry on with their duty. Eastwood’s Marine Gunnery Sgt. Highway is a ramrod of a man and a regretful survivor of the Korean War battle that gives the film its name, who whips his recruits into shape under the gaze of a clueless lieutenant even as he tries to soften his rough edges to make himself appealing to his ex-wife (Marsha Mason). Eastwood is priceless both as the disciplinarian who gives his men the grit they need to perform and as the hapless romantic who resorts to reading Cosmopolitan magazine in an effort to understand the female of the species.

3. Dirty Harry (1971)

One of the all-time great movie characters was Eastwood’s Harry Callahan, the brutish enforcer whose disgust for the system is his weapon for cutting through the sanctimoniousness and procedural red tape that had swung the balance of power against victims and turned the law into a plaything of criminals. Eastwood’s pitiless stare enraged critics.

2. Million Dollar Baby (2004)

Hilary Swank won the Oscar but the film wouldn’t work without Eastwood’s gravelly gravitas as boxing trainer Frankie Dunn. Eastwood gave his patented toughness and authority a small twist this time, turning them into paternal love and devotion that gave the relationship between coach and athlete its emotional depth and made this among the most moving of Eastwood’s best films.