Sometimes the best way to beat the summer heat is to plug in the fan, grab an Otter Pop, and watch a movie. To that end, we put together our top summer recommendations for insurance-themed movies. But before we dig in, we should make one thing clear — we’re not film critics. We’re insurance agents, dedicated claims reps, and specialized investigators. For us, a little romance is fine, and action is okay, but for a film to really jump off the screen, it’s gotta have a tinge of insurance magic.

Our top 10 list isn’t your standard CGI-fueled, action-packed summer fare, but you might be amazed to see a few all-time classics.

Counting down, here’s the list of our 10 favorite insurance-themed movies.

10. The Incredibles (2004)

Okay, so it’s not exactly about insurance. But Bob Parr, aka Mr. Incredible, does play an insurance agent before losing his job for assaulting his boss, Mr. Hugh, at the fictional Insuricare. Being fired from Insuricare is the catalyst that leads Mr. Incredible to revitalize his career as a superhero. If only he’d done a better job assessing the risks!

9. Alias Jesse James (1959)

The incompetent Milford Farnsworth (played by the very competent Bob Hope), an insurance salesman, unknowingly sells the outlaw Jesse James a $100,000 life insurance policy. Upon realizing this, Milford is sent to protect his investment. But James has a plan of his own. This classic Western comedy is life insurance hijinx at its best, and it features a number of cameos from the likes of Bing Crosby, Roy Rogers, and James Garner. Talk about a star-studded cast.

8. The Killers (1946)

This Oscar-nominated film delves into the mystery surrounding the murder of the Swede (Burt Lancaster). Jim Reardon (Edmond O’Brien) investigates the Swede’s small life-insurance claim, but as he digs further into his past, Reardon discovers a trail of crime and betrayal that leads him to the beautiful and mysterious Kitty Collins (Ava Gardner). And then things really heat up — the way they so often do in the steamy world of insurance.

7. Lloyd’s of London (1936)

This film, which was also nominated for an Oscar, shows the rise of the famed British insurance company through the eyes of Jonathan Blake. While the plot sounds a bit “insurancy,” a budding romance between Blake and Lady Elizabeth Stacy was enough to make it one of 20th Century Fox’s first hits. Who knew a perfect balance of insurance and romance equates to box-office magic?

6. Accidents Will Happen (1938)

Eric Gregg is a successful young claims adjuster at Central Casualty Insurance. But his success puts him in harm’s way when he runs into trouble with a gang of insurance scammers. Gregg ultimately outsmarts them with a surprising strategy of his own. The film is notable, not necessarily for its plot, but because Gregg is played by future U.S. President Ronald Reagan.

5. Ossessione (1943)

Widely regarded as the first Italian neorealist film, Ossessione tells the story of Gino and Giovanna’s tumultuous romance. The 2 fall in love and devise a scheme to murder Giovanna’s husband and cash in on his life-insurance policy. The film is an adaptation of John M. Cain’s 1934 classic crime novel The Postman Always Rings Twice, which, oddly enough, didn’t feature the insurance fraud aspect. (Director: “What this story really needs is insurance! Benissimo!”)

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4. Sleuth (1972)

Milo Tindle (Michael Caine) is in love with Marguerite, the wife of Andrew Wyke (Laurence Olivier). In an interesting twist, Wyke, a famous mystery writer, uses his storytelling talents to hatch a foolproof insurance fraud scheme that he hopes will allow Milo to take Marguerite off his hands. Everything goes according to plan … until jealousy sets in. This insurance classic earned 4 Oscar nominations, including nominations for both Caine and Olivier.

3. The Thomas Crown Affair (1968)

Thomas Crown (Steve McQueen) has everything: looks, money, success. When he attempts to pull off the perfect crime stealing unstealable art, an insurance investigator (played by Faye Dunaway) is sent to solve the mystery. Sparks fly in arguably one of the greatest heist films ever made. So great, in fact, it was made again in a 1999 version starring Pierce Brosnan and Renee Russo.

2. The Apartment (1960)

You’ve seen this one, right? C.C. Baxter (Jack Lemmon) is just another employee at a huge New York City insurance company. That is, until he offers his Manhattan apartment to company execs for their extramarital affairs. The favors catapult Baxter up the corporate ladder, but when he finds out his love interest is the boss’ mistress, he’s faced with a tough decision: love or status. Making AFI’s list of Top 100 Films of All Time, The Apartment was nominated for 10 Oscars and won 4, including Best Picture.

1. Double Indemnity (1944)

Arguably one of the best noir films ever made (we said arguably), Double Indemnity follows the tale of an insurance agent (Fred MacMurray) who lets a damsel in distress (Barbara Stanwyck) convince him to defraud the company he works for in a life-insurance scam hinging on the murder of her husband. Since it’s a must-see, we don’t want to give away too much of the plot, so let’s just say, “Double indemnity indeed!”

So there you have it. Proof that the world of insurance is filled with intrigue, romance, mystery, and more plot twists than any actuary could have predicted. Okay, in real life, it’s not quite that exciting, but all of the films listed above show a little-known side of the insurance experience: investigation. And it’s fair to point out that although they haven’t won any Oscars, the Esurance Special Investigations Unit has made headlines and won industry recognition for their fair and thorough work. Kudos to them.

Whoever said insurance was boring?

Additional resources

Risk, Insurance, & the Movies
AFI’s 100 Years, 100 Movies
Your Netflix queue (hint, hint)

Insurance 101

about Paul

Paul is a Rideshare Specialist at Zimride. He's an avid blogger, both personally and professionally. To see more of his work, visit Zimride's blog.