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.
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]
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.
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
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.
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)
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!”