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25 best insurance movies: 21-25

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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 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.

Over the next five days, I’ll be releasing 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 or send me an email at [email protected]

 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?

Up next: Alias Jesse James

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.

Up next: The Killers

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.

Up next: Along Came Polly

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.

Up next: Evil Under the Sun

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.

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