25 best insurance movies, Pt. 1 (25-14)Article added by Daniel Williams on February 28, 2014
Daniel Williams

Daniel Williams

Centennial, CO

Joined: January 30, 2008

My Company

Who knew insurance could be so... cinematic? Well, Hollywood, for starters. In researching this project, I found that 1,634 movies and TV episodes come up in IMDB.com when searching the keyword "insurance."

The problem in drilling down to a top 25 has not been in finding quality films. Many on this list have been nominated for Academy Awards; a few have won golden statues. No, the bigger dilemma has been in finding variety among the films that carry an "insurance" hook.

There's no shortage of movies featuring insurance fraud and scheming spouses looking to off their mate for the life insurance policy. To avoid that monotony, not all of the selections deal with insurance specifically, but rather with characters who have, or had, careers in the insurance field. That made picking these movies more interesting for me, and, hopefully, will be for you as well.

Here is part one (25-14) of what I believe are 25 of the best insurance movies ever made or at least the best of the ones I've seen.

I welcome your thoughts on my selections and if you feel like I left any deserving movies off the list, please leave a comment below.

25. The Rainmaker (1997)

Starring: Matt Damon, Danny DeVito, Claire Danes

Directed by: Francis Ford Coppola

What's it about: A corrupt insurance company. An idealistic, young lawyer. It's a David vs. Goliath theme tailor-made for Hollywood.

Why watch it: I'm a sucker for a good David vs. Goliath story and The Rainmaker is a good one with a small-time legal eagle going up against a giant insurance corporation and its army of attorneys.

Interesting factoid: John Grisham's favorite of all the films adapted from his books.

Business takeaway: David had his Goliath and Rudy Baylor (Matt Damon, who looks about twelve) has his big insurance company. It might be just a movie, but when the unachievable goal stands in your path, it's only unachievable if you never take it on.

Memorable scene: Where Rudy Baylor (wow, how can you not root for an underdog named Rudy?) sits across the table from the team of attorneys representing the insurance company and goes toe-to-toe with all the guys in suits.

Memorable quote:

Rudy Baylor: I'm curious.

Leo F. Drummond: About what?

Rudy Baylor: I'm just wonderin'... do you even remember when you first sold out?

24. Alias Jesse James (1959)

Starring: Bob Hope, Rhonda Fleming, Wendell Corey

Directed by: Norman Z. McLeod

What's it about: It's the wild west and an inept insurance salesman, Milford Farnsworth (Bob Hope), sells a man a $100,000 life insurance policy. When Milford's boss learns the man was Jesse James, he sends an understandably nervous Milford after the outlaw to buy back the policy.

Why watch it: For the misdirection created by the infamous Jesse James hiding in plain site and for Hope's role as a shaky gunslinger.

Interesting factoid: The climactic gunfight features a cameo by Hope's buddy Bing Crosby and surprise appearances by actors who, at the time, were starring, or had recently starred, in popular Western television series (such as Maverick (1957), The Roy Rogers Show (1951), Annie Oakley (1954) and Western movies such as High Noon (1952).

Business takeaway: When you sell someone a policy, make sure they are who they say they are.

Memorable scene: The final shootout is a hoot. Milford (Bob Hope) may be the shakiest gun in the west, but with all of the big stars appearing in cameos for his benefit, they make it an easier job for him to get his man.

Memorable quote:

Titus Queasley: Farnsworth, what do you expect to achieve with such crass ineptitude, such utter incompetence, such colossal stupidity?

Milford Farnsworth: Well, I was hoping to become your assistant.

23. The Killers (1946)

Starring: Burt Lancaster, Ava Gardner, Edmond O'Brien

Directed by: Robert Siodmak

What's it about: A couple of hitmen get their man and an insurance investigator uncovers the dead man's past, a past that involves the beautiful and deadly Kitty Collins.

Why watch it: Arguably the best screen treatment of writer Ernest Hemingway’s work. The film is based on his classic short story of the same name. Also, in his first role, Burt Lancaster is spot-on as the laconic “Swede.”

Interesting factoid: Lancaster was an ex-circus acrobat before getting this first starting role. When producer Mark Hellinger saw the first rushes of Lancaster's performance in a private screening room, he was so pleased that he yelled "So help me, may all my actors be acrobats!"

Business takeaway: Sometimes, it’s okay to fold your cards if you don’t have the winning hand. Walk away. Live to fight another day.

Memorable scene: The dramatic first meeting between the Swede and Kitty Collins.

Memorable quote:

[after insurance agent Reardon has wrapped up the investigation, Kenyon congratulates him]

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.

[he shakes Reardon's hand]

R.S. Kenyon: Congratulations, Mr. Reardon.

Jim Reardon: I'd rather have a night's sleep.

22. Along Came Polly (2004)

Starring: Ben Stiller, Jennifer Aniston, Philip Seymour Hoffman

Directed by: John Hamburg

What's it about: Reuben Feffer (Ben Stiller, in the type of role he can do in his sleep) is a neurotic, risk-insurance salesman, who's trying to get his life back together after his newlywed bride dumps him on their honeymoon.

Why watch it: The romance is a yawner, seriously, but the late, great Philip Seymour Hoffman is terrific as a struggling, former child actor, and Reuben's best friend. His performance alone is worth watching the film and his greatness will be missed.

Interesting factoid: Ben Stiller mentioned while on a talk show promoting the film that the ferret bit him a couple of times during production, including one time latching onto his chin.

Business takeaway: Sometmes, being too nice can be too much of a "good" thing. Eventually, you have to grow a backbone if you want to get ahead in business and in life.

Memorable scene: Two words: Sasquatch basketball.

Memorable quote:

Reuben Feffer: I know that I have a .013% 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.

21. Evil Under the Sun (1982)

Starring: Peter Ustinov, James Mason, Maggie Smith

Directed by: Guy Hamilton

What's it about: Hercule Poirot (Peter Ustinov) is called in to investigate a case for an insurance company regarding a dead body and also a rare diamond that was insured by the company and turns out to be a fake.

Why watch it: This is the rare Agatha Christie adapaptation that surpasses the book and Ustinov is in rare form, truly embodying the dry wit of the famed sleuth.

Interesting factoid: It's the second of six appearances playing Detective Hercule Poirot by Peter Ustinov. Ustinov played Poirot here between playing him in the movies Death on the Nile (1978) and Thirteen at Dinner (1985).

Business takeaway: If you have a fox in the henhouse of your place of business, hire a great detective to find out who the culprit is.

Memorable scene: The summation, of course, with Poirot (Ustinov) gathering the cast of characters to go over all of the clues, throw out a few red herrings and reveal the murderer.

Memorable quote:

Christine Redfern: I'm better now. In fact, I'm determined to enjoy myself. It's so blissful here, so tranquil, so far from all violence and trouble.

Poirot: Yes, you are right, Madame; the sky is blue, the sun is shining, and yet, you forget that everywhere there is evil under the sun.

20. John Q (2002)

Starring: Denzel Washington, Robert Duvall, Gabriela Oltean

Directed by: Nick Cassavetes

What's it about: A down-on-his luck father, whose insurance won't cover his son's heart transplant, takes the hospital's emergency room hostage until the doctors agree to perform the operation.

Why watch it: To see Denzel go all Denzel on the hospital and its employees. He’s one of the rare actors who can illicit sympathy while going on a rampage.

Interesting factoid: The scene where George W. Bush is speaking about health care while John (Denzel Washington) and Denise (Kimberly Elise) are watching TV, was also shot with footage of Al Gore because the election winner had not yet been declared at the time of the film's shooting.

Business takeaway: That the horrors over the health care system have been raging since well before Obamacare made it a daily conversation piece. As John Q. puts it: "My son is dying, and I'm broke. If I don't qualify for Medicare, who does?"

Memorable scene: The horrifying scene when John Q.’s (Denzel’s) son collapses at the ball field. It's one of those moments any parent hopes to never experience.

Memorable quote:

John Q. Archibald: The hospital is under new management now! Free health care for everyone!

19. The Fortune Cookie (1966)

Starring: Jack Lemmon, Walter Matthau, Ron Rich

Directed by: Billy Wilder

What's it about: When an NFL cameraman (Jack Lemmon) is knocked over during a football game, his shyster brother-in-law, Whiplash Willie Gingrich (Walter Matthau), convinces him this is their big payday, so they sue CBS, the NFL and the Cleveland Browns for damages.

Why watch it: For the great chemistry between Lemmon and Matthau, who would gain greater acclaim in The Odd Couple, but who put their initial stamp down here as one of cinema’s great comedy teams.

Interesting factoid: Marked the first pairing of Jack Lemmon and Walter Matthau, who subsequently worked together on eleven additional films.

Business takeaway: Even if good intentions are your motivation, remember that crime doesn’t pay. Well, maybe it pays, but not without repercussions.

Memorable scene: There's a terrific sequence with Whiplash Willie (Matthau) where he’s on the phone, his wife is cooking dinner and their kids are roller-skating through the house. His fraudulent scheme is unraveling and we can experience this through the whirlwind nature of his homelife.

Memorable quote:

Professor Winterhalter: All these newfangled machines. Fake! It proves nothing. In the old days, we used to do these things better. The man says he's paralyzed, we simply throw him in the snake pit. If he climbs out, then we know he's lying.

Specialist #1: [shocked] And if he doesn't climb out?

Professor Winterhalter: Then we have lost the patient, but we have found an honest man.

18. Ossessione (1943)

Starring: Clara Calamai, Massimo Girotti, Dhia Cristiani

Directed by: Luchino Visconti

What's it about: Ossessione, made in 1943 and banned in Italy by Mussolini, is the first adaptation of James M. Cain's The Postman Always Rings Twice. It’s not as strong as Cain’s Double Indemnity (what is?), but it follows a similar thread: Can illicit lovers kill the woman’s unsavory husband and cash in on his life insurance policy?

Why watch it: Ossessione is the film that launched the neorealism movement. While it can try on the patience with its deliberate style, Ossessione is a superior version than either of the American adaptations of James M. Cain’s, The Postman Always Rings Twice.

Interesting factoid: Fascists destroyed the film’s negative. Luckily, director Luchino Visconti managed to save a print.

Business takeaway: If your spouse is 20 years younger and, to put it bluntly, much better looking, a prenup might be in order. Also, if a muscular, young man starts hanging around your wife, he’s probably not there to ask about the weather.

Memorable scene: The haunting moment where the smoldering stranger (Massimo Girotti) hears the café owner’s wife (Clara Calamai) singing and is drawn to her heavenly voice.

Memorable quote:

Gino Costa: Do you know the fat man?

Giovanna Bragana: He’s my husband.

Gino Costa: He’s lucky to have such a lady. One that cooks so well.

Giovanna Bragana: Save your breath. Anyway, I’m not a cook.

17. Fletch (1985)

Starring: Chevy Chase, Joe Don Baker, Dana Wheeler-Nicholson

Directed by: Michael Ritchie

What's it about: Los Angeles journalist, Irwin "Fletch" Fletcher (Chevy Chase) is working in disguise as a bum on the beach to investigate a drug ring. One day he's approached and asked to kill a rich man for the sum of $50,000 so the rich guy's wife can get the insurance money.

Why watch it: A little Chevy Chase can go a long way, and while he does have his hammy moments here, Fletch is his most complete role and he’s perfect in it.

Interesting factoid: Gregory McDonald, the author of the Fletch novels, had casting approval over the film. He rejected both Mick Jagger and Burt Reynolds before he decided on Chevy Chase for the lead.

Business takeaway: Identity theft is a real problem. Make sure you have the necessary channels set up to protect your identity, assets and accounts.

Memorable scene: The proctology exam where Fletch (Chevy Chase) begins crooning “Moon River.” Memorable quotes

Gail Stanwyk: I didn't know you knew the Underhills.

Fletch: Yeah, well, I saved his life during the war.

Gail Stanwyk: You were in the war?

Fletch: No, he was. I got him out.

16. To Catch a Thief (1955)

Starring: Cary Grant, Grace Kelly, Jessie Royce Landis

Directed by: Alfred Hitchcock

What's it about: American expatriate John Robie (Cary Grant) is living the good life on the Riviera. He's also a retired cat burglar who must find out who the copycat thief is responsible for the rash of jewel heists being pinned on him. Enter a gorgeous Lloyd's of London insurance agent (Grace Kelly) who uses a a thief to catch a thief.

Why watch it: Hitchcock and the stars, Cary Grant and Grace Kelly, are all in fine form here. Whether all the leads were having fun, I have no idea, but they sure look like they are.

Interesting factoid: On September 14, 1982, Grace Kelly was killed in an automobile accident in Monaco, supposedly on the very same road as her famous chase scene in this film and not far from where she had a picnic scene with Cary Grant. She was 52 years old and lost control of her car after apparently suffering a stroke while at the wheel.

Business takeaway: It takes a thief to catch a thief.

Memorable scene: The brilliant opening sequence where we see a black cat running wild on the roofs of villas, and, later on, hysterical ladies are seen screaming when they realize they have been burglarized.

Memorable quote:

John Robie: [In reference to a beautiful villa they are visiting] Why don't you own a place like this?

Frances Stevens: Palaces are for royalty. We're just common people with a bank account.

15. Kafka (1991)

Starring: Jeremy Irons, Theresa Russell, Joel Grey

Directed by: Steven Soderbergh

What's it about: Loosely based on German novelist Franz Kafka’s unfinished novel, The Castle, this cinematic version follows the writer and insurance company employee, Kafka (Jeremy Irons in the titular role), as he stumbles upon an underground society and attempts to uncover their next terrorist activity.

Why watch it: From the start of his career, director Steven Soderbergh has, more than any filmmaker of his generation, successfully jumped back and forth between mainstream movies and artsy films. Kafka clearly resides on the “artsy” side. Creepy, enigmatic, Kafka's not a tidy story where the plot and purpose were sketched out on a napkin in crayon by studio executives. The film, like its subject (Franz Kafka), offers few, obvious answers, but opens a door for the viewer to ponder: The lofty idea of "'man' as individual and his place and purpose in modern society." And, if all that just sounds too far out, then watch Kafka for the lush, black-and-white cinematography and the haunting musical score.

Interesting factoid: When searching for his missing colleague in the Cafe Continental, Kafka is approached by friends and they ask: "What are you working on?" Kafka replies: "A thing about a man who wakes up and finds himself transformed into a giant insect!" A direct reference to Kafka's best known work, "Die Verwandlung," or as we refer to it in the English translation, The Metamorphosis.

Business takeaway: If you think you're in a dead-end job, you probably are. As a business guru told me 20 years ago, "Do what you love and the money will follow." I quit my Kafka-esque job by week's end and have supported myself by writing ever since.

Memorable scene: The comedic moment where the twins at the insurance company engage in a speed-typing contest.

Memorable quote:

Doctor Murnau: A crowd is easier to control than an individual. A crowd has a common purpose. The purpose of the individual is always in question.

Franz Kafka: That's what you're trying to eliminate, isn't it? Everything that makes one human being different from another. But you'll "never", "never" reach a man's soul through a lens.

Doctor Murnau: That rather depends on which end of the microscope you're on, doesn't it?

14. Lloyd’s of London (1936)

Starring: Tyrone Power, Madeleine Carroll, Freddie Bartholomew

Directed by: Henry King

What's it about: When tweens Jonathan Blake (Freddie Bartholomew) and Horatio Nelson (Douglas Scott) learn that sailors/pirates are planning to swindle an insurance company, they trek to London to warn the owners of "Lloyd's Coffee-House." Their news eventually results in a job with the company for Blake (Tyrone Power plays him as an adult), who eventually becomes an owner of "Lloyd's of London."

Why watch it: Though Blake is a fictional character, the film, besides being a good action yarn, provides an origin story to the venerable Lloyd's of London.

Interesting factoid: Lloyd's of London was future superstar, Tyrone Power's, first leading role, and, at the tender age of 23, he showed the studio heads he had the chops to carry a film.

Business takeaway: Doing a good deed can lead to good things happening to you. i.e. Pay it forward.

Memorable scene: The spy subplot, where Blake is involved in passing along false information to enemy troops, thus enabling Admiral Nelson valuable time so he can win the Battle of Trafalgar.

Memorable quote:

Lord Stacy: Ah, yes, I recall your face. You're a waiter at Lloyd's Coffee-House, aren't you?

Blake: Yes. I am at Lloyd's.

[They're interrupted by the young woman Blake has been romancing.]

Lady Elizabeth: Mr. Blake, I'd like you to meet my husband, Lord Stacy.

Originally published on LifeHealthPro.com
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