The calculating antihero in 'Charley Varrick' (1973)
Forget the lovable grump; here Matthau is a cold, calculating professional. He plays a crop-duster pilot and small-time bank robber who accidentally steals a massive sum of money from the mob. What follows is a tense cat-and-mouse game, not just with
the police, but with a relentless hitman sent to retrieve the cash. Directed by Don Siegel, this neo-noir thriller showcases a side of Matthau rarely seen: a tough, resourceful antihero who is always the smartest person in the room. It’s a sharp, gritty performance that proves he was just as compelling in a high-stakes thriller as he was trading insults with Jack Lemmon.
The cynical moral center in 'A Face in the Crowd' (1957)
In one of his earliest significant film roles, Matthau holds his own in Elia Kazan's terrifyingly prescient drama about media and power. While Andy Griffith gives a powerhouse performance as 'Lonesome' Rhodes, a folksy entertainer who becomes a monstrous demagogue, Matthau plays Mel Miller, a writer who sees through the facade from the very beginning. As Mel, Matthau is the film’s conscience, delivering his lines with a world-weary skepticism that provides a grounding counterpoint to Rhodes' unchecked charisma. It's a quiet, intellectual performance that stands in stark contrast to the boisterous characters he would later become famous for playing.
The shyster lawyer in 'The Fortune Cookie' (1966)
This is the one he won the Oscar for, yet it's often forgotten in the shuffle of his more famous comedies. In his first on-screen pairing with Jack Lemmon, Matthau plays 'Whiplash Willie' Gingrich, a shamelessly crooked lawyer who convinces his brother-in-law to fake a major injury for a massive insurance payout. Matthau is pure comedic dynamite, a whirlwind of amoral energy and hilarious schemes. While he and Lemmon would perfect their chemistry over nine more films, this is where it all began, with Matthau creating a character so deliciously slimy and funny that the Academy simply couldn't ignore it.
The homicidal playboy in 'A New Leaf' (1971)
This pitch-black comedy, written and directed by Elaine May, features Matthau in one of his most daring roles. He plays Henry Graham, a bankrupt, self-absorbed playboy who decides his only option is to marry a wealthy, awkward botanist (played by May) and then murder her. The film is a masterclass in tone, and Matthau navigates it perfectly. His Henry is both monstrously selfish and, somehow, increasingly sympathetic. It's a viciously funny performance that weaponizes his signature grumpiness, turning it from a lovable quirk into a genuinely menacing, and ultimately hilarious, character trait.
The unflappable transit cop in 'The Taking of Pelham One Two Three' (1974)
In one of the quintessential New York City thrillers, Matthau is the picture of beleaguered competence. He plays Lt. Zachary Garber of the transit police, the man on the other end of the radio when a subway car is hijacked by a group of ruthless criminals led by Robert Shaw. Garber isn't a superhero; he's a civil servant with a cold, an everyman tasked with an impossible situation. Matthau plays him with a masterful deadpan, navigating the high-stakes negotiations with cynical humor and weary professionalism. It’s a grounded, utterly believable performance that anchors the entire film and makes the tension feel real.
