As the world continues its discussion of this year’s Oscar winners and losers, the Insurance Information Institute has put together its own list of movies worth celebrating—those film in which insurance plays a starring role (a couple of them have even garnered Oscars of their own). Over the past 65 years, these films have featured Hollywood legends including Edward G. Robinson, Cary Grant and Faye Dunaway and in more recent years, popular actors such Jack Nicholson and Jennifer Aniston.
Double Indemnity (1944)
Director: Billy Wilder; Cast: Fred MacMurray, Barbara Stanwyck, Edward G. Robinson
In this classic film noir, smitten insurance man Walter Neff (MacMurray) plots the perfect murder with femme fatale client Phyllis Dietrichson (Stanwyck): Stage her husband’s “accidental” death to collect double indemnity on his life insurance, then abscond with the loot. But the lethal duo must first get past a crafty claims investigator (Robinson) who senses something isn’t kosher. What ensues is a cat-and-mouse game with fatal consequences.
Oscar Count: 7 nominations
Quote: The job I’m talking about takes brains and integrity. It takes more guts than there is in 50 salesmen. It’s the hottest job in the business… Desk job? Is that all you can see in it? Just a hard chair to park your pants on from 9 to 5, huh? Just a pile of papers to shuffle around and five sharp pencils and a scratch pad to make figures on. Maybe a little doodling on the side. Well, that’s not the way I look at it, Walter. To me, a claims man is a surgeon. That desk is an operating table. And those pencils are scalpels and bone chisels. And those papers are not just forms and statistics and claims for compensation, they’re alive, they’re packed with drama, with twisted hopes and crooked dreams. A claims man, Walter, is a doctor and a bloodhound… and a cop and a judge and a jury and a father confessor all in one.
Director: Christopher Nolan; Cast: Guy Pearce, Carrie-Anne Moss, Joe Pantoliano
Suffering short-term memory loss after a head injury, ex-insurance investigator Leonard Shelby (Pearce) embarks on a grim quest to find the lowlife who murdered his wife. To carry out his plan and compensate for his disability Shelby snaps Polaroids of people and places, jotting down contextual notes on the backs of the photos, and tattoos important facts on his body.
Oscar Count: 2 nominations
Quote: Memory’s unreliable. No no no, really. Memory’s not perfect; it’s not even that good. Ask the police. Eyewitness testimony is unreliable. Cops don’t catch a killer by sitting around remembering stuff. They collect facts, they make notes and they draw conclusions. Facts, not memories. That’s how you investigate. I know. It’s what I used to do. Look, memory can change the shape of a room; it can change the color of a car. And memories can be distorted. They’re just an interpretation, they’re not a record, and they’re irrelevant if you have the facts.
The Fortune Cookie (1966)
Director: Billy Wilder; Cast: Jack Lemmon, Walter Matthau
Shyster William Gingrich (Matthau) foresees a financial bonanza after Cleveland Browns star “Boom Boom” Jackson accidentally levels cameraman Harry Hinkle (Lemmon), Gingrich’s brother-in-law. Barely hurt, Hinkle is loath to help Gingrich scam the insurance company till realizing the moola might lure back his ex. A budding rapport with the guilt-ridden Jackson, however, begins gnawing at Hinkle’s conscience.
Oscar Count: 4 nominations; 1 win–Walter Matthau, Best Actor in a Supporting Role
Quote: Too bad it didn’t happen further down the street… in front of the May Company. From them, you can collect! Couldn’t you have dragged yourself another 20 feet?
The Killers (1946)
Director: Robert Siodmak; Cast: Burt Lancaster, Ava Gardner, Edmond O’Brien
Two professional killers invade a small town and kill a gas station attendant, the “Swede” (Lancaster), who is expecting them. Insurance investigator Jim Reardon (O’Brien) pursues the case against the orders of his boss, who considers it trivial. Weaving together threads of the ex-prize fighter’s life, Reardon uncovers a complex tale of treachery and crime, all linked with gorgeous, mysterious Kitty Collins (Gardner).
Oscar Count: 4 nominations
Quote: [last lines]
R.S. Kenyon: Owing to your splendid efforts the basic rate of The Atlantic Casualty Company—as of 1947—will probably drop one-tenth of a cent. Congratulations, Mr. Reardon.
Jim Reardon: I’d rather have a night’s sleep.
R.S. Kenyon: Why don’t you take a good rest. I must say you’ve earned it… This is Friday—don’t come in ’til Monday.
Jim Reardon: Thanks.
Save the Tiger (1973)
Director: John G. Avildsen; Cast: Jack Lemmon, Jack Gilford
Synopsis: Harry Stoner (Lemmon, in an Oscar-winning performance) is a Los Angeles dress manufacturer whose business is on the skids. In a desperate move—and against the dictates of his conscience—he hires an arsonist to torch his building so he can collect the insurance payout. Jack Gilford also earned an Oscar nomination for his performance as Harry’s partner and best friend.
Oscar Count: 3 nominations, 1 win–Jack Lemmon, Best Actor in a Leading Role
Quote: The government has a word for survival. It’s called fraud.
The Thomas Crown Affair (1968); The Thomas Crown Affair (1999)
 Director: Norman Jewison; Cast: Steve McQueen, Faye Dunaway/ Director: John McTiernan; Cast: Pierce Brosnan, Rene Russo
The story of bored, multimillionaire playboy Thomas Crown (McQueen/Brosnan) who opts for a life of crime. In the original movie, he masterminds a bank robbery; in the remake, he steals a priceless work of art. A beautiful insurance investigator (Dunaway/Russo) sets out to catch him, but ends up seduced by her quarry’s charms.
Oscar Count: 1968: 2 nominations; 1 win – Best Music, Original Song “The Windmills of Your Mind”; 1999: 0
Psychiatrist: Has it occurred to you that you have a problem with trust?
Thomas Crown: I trust myself implicitly.
Psychiatrist: But can other people trust you?
Thomas Crown: Oh, you mean society at large?
Psychiatrist: I mean women, Mr. Crown.
Thomas Crown: Yes, a woman could trust me.
Psychiatrist: Good. Under what extraordinary circumstances would you allow that to happen?
Thomas Crown: A woman could trust me as long as her interests didn’t run too contrary to my own.
Psychiatrist: And society? If its interests should run counter to your own?
To Catch a Thief (1955)
Director: Alfred Hitchcock; Cast: Cary Grant, Grace Kelly, Jessie Royce Landis
A Lloyd’s of London insurance agent uses a thief to catch a thief when John Robie (Grant), a reformed jewel thief, is suspected in a new series of gem heists in the luxury hotels of the French Riviera. Robie sets out to clear himself with the help of pampered heiress Frances (Kelly), whose mother, Jesse Stevens, is one of the thief’s prime targets.
Oscar Count: 3 nominations; 1 win–Best Cinematography, Color
John Robie: Why did I take up stealing? To live better, to own things I couldn’t afford, to acquire this good taste that you now enjoy and which I should be very reluctant to give up.
H. H. Hughson: Then you are frankly dishonest.
John Robie: I try to be.
Along Came Polly (2004)
Director: John Hamburg; Cast: Ben Stiller, Jennifer Aniston, Philip Seymour Hoffman, Debra Messing, Hank Azaria
Reuben Feffer (Stiller) works as a risk analyst for an insurance company and believes that if you plan ahead and play it safe, you can have a pretty good life. When his wife of a few days (Messing) dumps him on his honeymoon for their scuba-diving instructor (Azaria), Reuben vows to keep things under an even tighter lid. But along comes Polly (Aniston), a bright, buoyant and breathtakingly irreverent childhood friend who teaches him to live life on the edge.
Oscar Count: 0
Quote: I know that I have a .013 percent chance of being hit by a car on my way home. Or a one in 46,000 chance of falling through a subway grate. So I try to manage that risk by avoiding danger and having a plan and knowing what my next move is. And I guess you don’t exactly live your life that way. Yeah… which is great, but I’m not gonna ever be a dirty dancer, and I don’t eat food with my hands, and I really like you, but I just don’t think this is gonna work out.
Other Insurance Films
About Schmidt (2003)
Accidents Will Happen (1938)
The Apartment (1960)
Barton Fink (1991)
The Big Squeeze (1996)
Changing Lanes (2002)
The Curse of the Jade Scorpion (2001)
2 Days in the Valley (1996)
Death Sentence (2007)
Dead by Dawn (1998)
Four Dogs Playing Poker (1999)
Gold Diggers of 1937 (1936)
The Granny (1995)
I Now Pronounce You Chuck & Larry (2007)
The Invisible Informer (1946)
John Q (2002)
The Ladykillers (1955)
Lucky Numbers (2000)
Proof of Life (2000)
The Running Man (1963)
The Truman Show (1998)
Weekend at Bernie’s (1989)
The Wreck of the Mary Deare (1959)
The Wrong Man (1956)
The Yellow Rose of Texas (1944)
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