25 best insurance movies, Pt. 2 (1-13)Article added by Daniel Williams on March 7, 2014
Daniel Williams

Daniel Williams

Centennial, CO

Joined: January 30, 2008

My Company

Here is part two (1-13) of what I believe are 25 of the best insurance movies ever made, or at least the best of the ones I've seen. (See part one here.)

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.

13. Save the Tiger (1973)

Starring: Jack Lemmon, Jack Gilford, Laurie Heineman

Directed by: John G. Avildsen

What's it about: Harry Stoner (Jack Lemmon) has tried everything to save his apparel business. First, he cooked the books. Then, he hired prostitutes for his clients. Finally, after all else has failed, he resorts to an arsonist to burn the place down so he can collect on the insurance.

Why watch it: Jack Lemmon’s performance. I’ve always admired his work, but when watching movies in the ‘70s, Lemmon was never one of my heroes. That lofty perch was held by the more macho actors like Steve McQueen, Robert Redford, Paul Newman, and the like (okay, guilty pleasure alert: Burt Reynolds), but, as I get older, and watch Lemmon's movies again, I find the nuances and subtle emotions of greatness.

Interesting factoid: Jack Lemmon admitted to having had a serious drinking problem at one time, which is one reason he looks back on his Oscar-winning role as Harry Stoner in Save the Tiger as perhaps the most gratifying, emotionally fulfilling performance of his career.

Business takeaway: It’s a list of things “not” to do: If you own a business, don’t juggle the books. Don’t set your factory on fire. Don't offer prostitutes to your clients. Don’t get involved in insurance scams of any kind.

Memorable scene: The speech Harry Stoner (Lemmon) gives at the fashion show is one of those “Oscar” moments and probably what helped Lemmon win for best actor that year.

Memorable quote:

Myra: Are you okay? Do you want something?

Harry Stoner: Yes. I want that girl in a Cole Porter song. I wanna see Lena Horne at the Cotton Club. Hear Billie Holiday sing "Fine and Mellow." Walk in that kind of rain that never washes perfume away. I wanna be in love with something. Anything. Just the idea. A dog, a cat. Anything. Just something.

12. Sleuth (1972)

Starring: Laurence Olivier, Michael Caine

Directed by: Joseph L. Mankiewicz

What's it about: Lovers. Rivals. Deadly games. Insurance policies. Did I say, deadly games? Yes. And that only scratches the surface of this complex, psychological thriller.

Why watch it: For the many guises that characters Andrew Wyke (Laurence Olivier) and Milo Tindle (Michael Caine) assume. At its core, Sleuth is an actor’s film more than it is a director’s and that’s why the remake by Kenneth Branagh in 2007 is such a pale comparison.

Interesting factoid: Michael Caine was so beside himself to be working with Laurence Olivier, that he didn't even know how to address him. Eventually, he broke down and just asked. Olivier replied, "Well I am the Lord Olivier and you are Mr. Michael Caine. Of course that's only for the first time you address me. After that I am Larry and you are Mike."

Business takeaway: If a deal sounds too good to be true, well, you know the rest.

Memorable scene: The rough and tumble moment where Michael Caine gets Lord Olivier in a hammerlock and feigns arresting him. It actually looks like it hurts. Your heart goes out to the older actor.

Memorable quote:

Milo Tindle: We are from different worlds, you and me, Andrew. In mine, there was no time for bright fancies and happy inventions, no stopping for tea. The only game we played was to survive, or go to the wall. If you didn't win, you just didn't finish. Loser, lose all. You probably don't understand that.

11. Memento (2000)

Starring: Guy Pearce, Carrie-Anne Moss, Joe Pantoliano

Directed by: Christopher Nolan

What's it about: Leonard, an ex-insurance investigator, can no longer build new memories. Using tattoos and scattered notes, he attempts to find the murderer of his wife, which is the last thing he remembers.

Why watch it: To see the theme of memory and identity that runs through director Christopher Nolan’s films (The Dark Knight Trilogy, Inception, etc.).

Interesting factoid: "The medical condition experienced by Leonard in this film is a real condition called Anterograde Amnesia, the inability to form new memories after damage to the hippocampus. During the 1950s, doctors treated some forms of epilepsy by removing parts of the temporal lobe, resulting in the same memory problems."

Business takeaway: Get a really, really, good day planner.

Memorable scene: When Leonard Shelby (Guy Pearce) realizes he’s running and that he's running parellel to another man. At first, he thinks he’s chasing the man, but when the other guy pulls a gun, Leonard realizes he’s the one being chased. It’s a microcosm of the entire movie, of Leonard’s patchwork existence and blocked memory.

Memorable quote:

Leonard Shelby: I have to believe in a world outside my own mind. I have to believe that my actions still have meaning, even if I can't remember them. I have to believe that when my eyes are closed, the world's still there. Do I believe the world's still there? Is it still out there?... Yeah. We all need mirrors to remind ourselves who we are. I'm no different.

Up next: The Truman Show

10. The Truman Show (1998)

Starring: Jim Carrey, Ed Harris, Laura Linney

Directed by: Peter Weir

What's it about: An insurance salesman/adjuster discovers his entire life is actually a TV show.

Why watch it: Made in 1998, a few years before reality TV seemed to take over the media and our lives, The Truman Show is all the more frightening now, as its voyeuristic message has taken on a creepy realism through social media and Honey Boo Boo.

Interesting factoid: The Latin motto on the double archway in the Seahaven town center is UNUS PRO OMNIBUS, OMNES PRO UNO, translated to English as: "One for all, all for one," thus fitting the premise of the show within The Truman Show.

Business takeaway: What is fact and what is fiction? What, in your life, is truly authentic? Those are the questions to ask yourself as you go through your day, sell products and cultivate relationships.

Memorable scene: The scene (in the video above), where Truman’s morning begins. The scene's “payoff,” both literally and figuratively, is when the town’s twins push Truman against a product placement sign, giving us a moment that is both hilarious and terrifying.

Memorable quote:

Truman: Good morning, and in case I don't see ya, good afternoon, good evening and good night!

9. Death of a Salesman (TV 1985)

Starring: Dustin Hoffman, Kate Reid, John Malkovich

Directed by: Volker Schlöndorff

What's it about: The Arthur Miller play comes to life in this made-for-TV version, also penned by Miller. It's the classic tale of Willy Loman (Dustin Hoffman) a traveling insurance salesman who is slowly losing his mind and his will to live.

Why watch it: You might be familiar with the play, but Hoffman's incendiary performance as Willy Loman makes it well worth another viewing.

Interesting factoid: It took three and a half hours for makeup artists to transform Dustin Hoffman, then in his forties, into Willy, who is described in the stage directions as "over sixty".

Business takeaway: You are only as big as your dreams, but to realize those dreams you have to be willing to take the first step.

Memorable scene: Where Biff (John Malkovich) visits Willy at the hotel in Boston forever changing the direction of both of their lives.

Memorable quote:

Biff Loman: [arguing with Willy] Pop, I'm a dime a dozen and so are you...

Willy Loman: [shouting] I am not a dime a dozen! I'm Willy Loman and you are Biff Loman!

Biff Loman: [to his father] Will you let me go, for Christ's sake? Will you take that phony dream and burn it before something happens?

8. About Schmidt (2002)

Starring: Jack Nicholson, Hope Davis, Dermot Mulroney

Directed by: Alexander Payne

What's it about: Upon retirement from the life insurance industry, Schmidt (Jack Nicholson), finds himself adrift and sets out on an existential quest, even if he wouldn't call it that, to find purpose for this new chapter in his life.

Why watch it: Known for playing outlandish characters who take over the screen with bravado and charisma, Nicholson goes subtle and small in this performance and it’s his best work in decades.

Interesting factoid: When Jack Nicholson met Alexander Payne to discuss his role, Payne had a one-sentence directive for him; it was "Jack, I want you to play a small man."

Business takeaway: What if our life’s work was just that, work? Don’t wait until it’s too late to find you’re life’s purpose.

Memorable scene: The opening “wordless” sequence that tells us so much about Schmidt without ever uttering a word.

Memorable quote:

Warren Schmidt: Relatively soon, I will die. Maybe in 20 years, maybe tomorrow, it doesn't matter. Once I am dead and everyone who knew me dies too, it will be as though I never existed. What difference has my life made to anyone? None that I can think of. None at all.

Up next: Groundhog Day

7. Groundhog Day (1993)

Starring: Bill Murray, Andie MacDowell, Chris Elliott

Directed by: Harold Ramis

What's it about: A cynical weatherman (Bill Murray), sent to cover the annual Groundhog Day, finds himself trapped living the same day over and over again.

Why watch it: If for no other reason, then do it for Ned Ryerson, Needle Nose Ned. He’d do it for you. Bing!

Interesting factoid: Bill Murray was bitten by the groundhog twice during shooting. Murray had to have anti-rabies injections because the bites were so severe.

Business takeaway: Live every day as if it’s the only one you have. Because, "today" it is the only time you’ll ever have this one.

Memorable scene: I love the ice sculpture set piece and any of the smarmy moments with Chris Elliott, but the interaction between Murray’s weatherman and insurance salesman Ned Ryerson are classic.

Memorable quote:

Ned: Do you have life insurance, Phil? Because if you do, you could always use a little more, right? I mean, who couldn't? But you wanna know something? I got the feeling...


Ned: ... you ain't got any. Am I right or am I right? Or am I right? Am I right?

6. The Thomas Crown Affair (1968)

Starring: Steve McQueen, Faye Dunaway, Paul Burke

Directed by: Norman Jewison

What's it about: An international playboy has everything, or does he? Unfulfilled with living the good life, he turns to crime only to have a sexy insurance investigator (is that an oxymoron?) hot on his trail.

Why watch it: The interplay between Steve McQueen and Faye Dunaway is the reason why stars play out their characters’ lives on the big screen, and why we pay big bucks to go see them. Also, check out the remake with Pierce Brosnan and Renee Russo, it’s a rarity in film—a remake almost as good as the original.

Interesting factoid: The one-minute kissing sequence between the two leads took eight hours to film over a number of days.

Business takeaway: Be happy with what you have. If you’re bored being rich, start a foundation like Bill Gates.

Memorable scene: The chess match, which is about so much more than the match itself.

Memorable quote:

Sandy: You're mad! Absolutely mad!

Thomas Crown: What else can we do on Sunday?

5. Cedar Rapids (2011)

Starring: Ed Helms, John C. Reilly, Anne Heche

Directed by: Miguel Arteta

What's it about: Think what would happen in The Hangover if it took place in Cedar Rapids, Iowa instead of Las Vegas and if all the characters were small-town insurance agents.

Why watch it: It’s raunchy, sure, but if you’ve ever been to an insurance industry event, Cedar Rapids is a how-to manual of what not to do.

Interesting factoid: The hotel wedding that Tim Lippe (Ed Helms) and his friend's crash is for two women. Same-sex marriage has been legal in the state of Iowa since April 3, 2009.

Business takeaway: There’s a right way and a wrong way to conduct your business at an industry event and our everyman, Tim Lippe, manages to do a little of both.

Memorable scene: The skinny dipping scene at the hotel pool where Dean Ziegler (John C. Reilly) wears a metal trashcan on his head.

Memorable quote:

Tim Lippe: Do you realize I used to just stare and stare at you when you were teaching us about the rainforests or whatever? And I would think, "I wonder what Mrs. V. looks like with her clothes off." And then, boom, we run into each other in line at True Value and, boom, here we are making love. Like, once a week. It's like it was fate or something. Did you ever used to look at me and think dirty things?

Macy Vanderhei: You were twelve.

Tim Lippe: Right.

Up next: The Wrong Man

4. The Wrong Man (1956)

Starring: Henry Fonda, Vera Miles, Anthony Quayle

Directed by: Alfred Hitchcock

What's it about: When a struggling jazz musician (Henry Fonda) enters an insurance office to see if he can borrow off his wife’s life insurance policy to pay for her dental bills, he is mistaken for a serial thief and has to prove his innocence.

Why watch it: Hitchcock would return to his “wronged-man” theme in numerous films, but this is the only one based on a true story, which adds an extra level of tension to the master of suspense’s white-knuckled approach to filmmaking.

Interesting factoid: Although based on a true story, Alfred Hitchcock deliberately left out some of the information that pointed to Manny's innocence to heighten the tension.

Business takeaway: Sometimes, insurance doesn’t pay?

Memorable scene: The chilling moment when the police first stop Fonda on the street and tell him they need to ask a few questions. Though shot in beautiful black-and-white, those blue eyes of Fonda tell more than any words of dialogue could.

Memorable quote:

[first lines] Prologue narrator: This is Alfred Hitchcock speaking. In the past, I have given you many kinds of suspense pictures. But this time, I would like you to see a different one. The difference lies in the fact that this is a true story, every word of it. And yet it contains elements that are stranger than all the fiction that has gone into many of the thrillers that I've made before.

3. The Apartment (1960)

Starring: Jack Lemmon, Shirley MacLaine, Fred MacMurray

Directed by: Billy Wilder

What's it about: C. C. Baxter (Jack Lemmon) is a lower-middle manager in one of the five largest companies in the country. He also has an apartment that's convenient to the corporate headquarters and the perfect lover's nest for Baxter's bosses to bring their mistresses.

Why watch it: For the education on office politics and the perfect comic timing of Lemmon and Shirley MacLaine, who plays his love interest.

Interesting factoid: Although C.C. Baxter works at desk number 861, one of the thousands of employees for a giant insurance company, inside his apartment are two authentic Tiffany lamps. Worth hardly anything when the film was made, they're estimated to now be worth between $30,000 and $40,000 each.

Business takeaway: The climb to the top might be rife with pitfalls and other moral judgements. How much do you want that promotion and can you live with yourself if you compromise your morality?

Memorable Scene:The scene where Baxter makes Fran a spaghetti dinner, and, in typical bachelor fashion, strains the noodles with his tennis racket.

Memorable quotes:

C.C. Baxter: [narrating] On November 1st, 1959, the population of New York City was 8,042,783. If you laid all these people end to end, figuring an average height of five feet six and a half inches, they would reach from Times Square to the outskirts of Karachi, Pakistan. I know facts like this because I work for an insurance company - Consolidated Life of New York. We're one of the top five companies in the country. Our home office has 31,259 employees, which is more than the entire population of uhh... Natchez, Mississippi. I work on the 19th floor. Ordinary Policy Department, Premium Accounting Division, Section W, desk number 861.


C.C. Baxter: Miss Kubelik, one doesn't get to be a second administrative assistant around here unless he's a pretty good judge of character, and as far as I'm concerned you're tops. I mean, decency-wise and otherwise-wise.

2. The Incredibles (2004)

Starring: Craig T. Nelson, Samuel L. Jackson, Holly Hunter

Directed by: Brad Bird

What's it about: A former crime-fighter, Bob, is now just another bored suburbanite, pacing in his boring cubicle at Insuricare where the closest he gets to acts of derring-do is finding loopholes in insurance policies. That all changes when Bob and his superhero family are called back into action to save the world.

Why watch it: It never takes itself “too” seriously, as so many of the live-action superhero movies do, and, because of it, The Incredibles is better than 99.9% of them. Besides that, it’s a movie the whole family can watch and it’s funny, exciting and visually brilliant.

Interesting factoid: In the Singapore version of the film, the company “Insuricare” is translated into “Black-hearted insurance company” if read literally in the Chinese character subtitles.

Business takeaway: At one point in the movie, Mr. Incredible is called into his boss’s office and handed a memo stating that he will now be responsible for all of his own office supplies. At the bottom of the letter, he reads that Insuricare has "recorded its highest profits in years." If you ever get that memo, run, fast, to the nearest exit.

Memorable scene: So many, but one that’s subtle, yet endearing, is after Bob/Mr. Incredible has saved people from a burning building with his sidekick, Frozone, he is heard humming the Incredibles theme song. It let’s us all know: He’s not just an insurance adjustor any longer; he’s back to being… incredible!

Memorable quote:

[Bob is explaining an insurance policy loophole to a Mrs. Hogenson]

Bob: [whispering] Listen closely. I'd like to help you but I can't. I'd like to tell you to take a copy of your policy to Norma Wilcox on... Norma Wilcox, W-I-L-C-O-X... on the third floor, but I can't.

[Mrs. Hogenson scribbles details of Bob's loophole on a small notepad]

Bob: I also do not advise you to fill out and file a WS2475 form with our legal department on the second floor. I would not expect someone to get back to you quickly to resolve the matter. I'd like to help, but there's nothing I can do.

1. Double Indemnity (1944)

Starring: Fred MacMurray, Barbara Stanwyck, Edward G. Robinson

Directed by: Billy Wilder

What it's about: Phyllis Dietrichson (Barbara Stanwyck) doesn't like her husband. I mean, she really doesn't like him, and enlists the services of Walter Neff (Fred MacMurray), the top salesman at the Pacific All Risk Insurance Co., to help carry out the perfect crime.

Why watch it: Well, a few years back, the American Film Institute ranked Double Indemnity as the No. 29 greatest movie of all time. In addition, Stanwyck gives one of the silver screen's great villainous performances. Stanwyck's baddie is not the over-the-top type we're used to these days. Hers is a slow, slow burn that is both subtle and cruel in its execution.

Interesting factoid: The blonde wig that Barbara Stanwyck is wearing throughout the movie was the idea of Billy Wilder. A month into shooting Wilder suddenly realized how bad it looked, but by then it was too late to re-shoot the earlier scenes.

Business takeaway: Check the fine print on your insurance policies or any legal document before you sign them. You never know what you might find in there.

Memorable scene: When Phyllis and Walter meet for the first time, the double entendres erupt like machine gun fire. It's both seductive and dangerous and sets the tone for the rest of the movie.

Memorable quotes:

Barton Keyes: Well, I get darn sick of trying to pick up after a gang of fast-talking salesmen dumb enough to sell life insurance to a guy who sleeps in the same bed with four rattlesnakes.


Walter Neff: I was thinking about that dame upstairs, and the way she had looked at me, and I wanted to see her again, close, without that silly staircase between us.


Walter Neff: Yes, I killed him. I killed him for money — and a woman — and I didn't get the money and I didn't get the woman. Pretty, isn't it?
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