For our cover story on Robert Ryan, see J.R. Jones’s The Actor’s Letter: A reminiscence from film noir icon Robert Ryan, newly unearthed by his daughter, sheds light on his Chicago childhood – and his family’s connection to a tragic chapter in the city’s history. Ryan’s autobiographical letter is here.

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Crossfire (1948) Under contract to RKO, Ryan was usually cast as a young, heroic figure, but that changed with his chilling performance as Montgomery, the bullying, racist army sergeant in this socially conscious murder mystery by Edward Dmytryk. After a Jewish man is found dead in his own apartment, “Monty” turns up at the door, telling police that he’s looking for a missing friend; his cunning is evident in the way he seems to be defending the friend even as he directs suspicion toward him and away from himself. An eerie flashback to the night of the murder reveals Monty to be a hateful blowhard, ingratiating one moment, intimidating the next. The first American movie to deal explicitly with anti-Semitism, Crossfire was a box-office hit and earned Ryan his only Oscar nomination, for best supporting actor.

Caught (1949) Ryan may not have realized this at the time, but Smith Ohlrig, the controlling, egotistical millionaire he played in this noirish MGM romance, was based on his boss back at RKO—Howard Hughes. Director Max Ophuls had been walked on by Hughes while working for RKO, and he retaliated by adapting to the screen a novel by Libbie Block whose antagonist was a fictionalized version of the reclusive millionaire. Brilliant and decisive but deeply neurotic, Ohlrig marries a naive department store model to prove a point to his psychoanalyst, then keeps her a virtual prisoner in his palatial home. Ryan manages to make this misshapen man both repellent (check out the scene in which he sends a pool ball caroming around the table as he coolly calculates his wife’s motives and options) and pathetic (when she leaves him, he’s more vulnerable than ever).

The Wild Bunch (1969) With his rugged looks and athletic ability, Ryan was a natural for westerns and starred in a dozen of them over the years. Most of them are forgettable, but one changed the genre forever: Sam Peckinpah’s violent tale of four aging bandits who can outrun the law but not the 20th century. Ryan didn’t get quite as much screen time as William Holden, Ernest Borgnine, or Warren Oates, but he may have nabbed the most interesting role: Deke Thornton, the captured gang member who cuts a deal with the law to track down his former partners in exchange for his freedom. This “Judas goat” is plagued by guilt over his bargain and haunted by the bloody carnage that ensues as he leads a posse of wastrels across the Mexican border in pursuit of his old friends. “We’re after men,” he tells his worthless crew. “And I wish to God I was with them.”