(AP Photo/Don Ryan, File)

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 are what I believe are 25 of the best insurance movies ever made, or at least the best of the ones I’ve seen.

 25. The Rainmaker (1997)

Starring Matt DamonDanny DeVitoClaire 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 HopeRhonda FlemingWendell 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 LancasterAva GardnerEdmond 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 StillerJennifer 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 UstinovJames MasonMaggie 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)

Directed by Nick Cassavetes

Starring Denzel WashingtonRobert DuvallGabriela Oltean

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 LemmonWalter MatthauRon 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 CalamaiMassimo GirottiDhia 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 ChaseJoe Don BakerDana 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 GrantGrace KellyJessie 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)

Directed by Steven Soderbergh

Starring Jeremy IronsTheresa RussellJoel Grey 

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 PowerMadeleine CarrollFreddie 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. 

13. Save the Tiger (1973)

Directed by John G. Avildsen

Starring Jack LemmonJack GilfordLaurie Heineman 

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 OlivierMichael 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 PearceCarrie-Anne MossJoe 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.


10. The Truman Show (1998)

Starring Jim CarreyEd HarrisLaura 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 HoffmanKate ReidJohn 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 NicholsonHope DavisDermot 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.

7. Groundhog Day (1993)

Starring Bill MurrayAndie MacDowellChris 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 McQueenFaye DunawayPaul 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 HelmsJohn C. ReillyAnne 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.

4. The Wrong Man (1956)

Starring Henry FondaVera MilesAnthony 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)

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. NelsonSamuel L. JacksonHolly 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&rsqursquo;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 MacMurrayBarbara StanwyckEdward 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?