In 2020 many of us had a little extra time on our hands when we couldn’t get outside with our lives like normal. While we were certainly busy we also used some down time watching the occasional film or two – which inspired us to compile this list on films where insurance plays a major role…

  1. The Truman Show

After this 1998 movie about insurance adjuster Truman Burbank’s highly manipulated life came out there appeared actual cases of ‘The Truman Syndrome’ – people who believed their lives were reality television shows. The film’s writer, Kiwi Andrew Niccol, said “You know you’ve made it when you have a disease named after you.” We’re pretty sure any insurance consultant worth their salt would have recognised the statistical improbability of what kept Truman locked inside the small town of Seahaven. But then again, none of us have ever grown up in an artificial reality. Or… have we?

  1. Cedar Rapids

Released in 2011, this film is an occasionally raunchy (and sometimes cringe worthy) comedy with a warm heart. Ed Helms plays a naïve insurance agent who, finally venturing out of his hometown to an insurance conference, discovers there’s more to life than the ‘straight and narrow’. We love that while he encounters debauchery and corruption his belief in the strength of his work (“Insurance agents get people’s lives back on track.”) doesn’t waiver. It’s a good watch on a cold night.

  1. The Thomas Crown Affair

While the Steve McQueen/Faye Dunaway original is acceptable we prefer the 1999 remake, where Pierce Brosnan plays the suave multimillionaire art thief with Rene Russo opposite him as the skilled and insightful insurance investigator. The remake also has the memorable scene where the $100 million Monet turns out to be a cheap imitation painted over (what we consider to be) a superior piece – the legendary ‘Dogs playing poker’.

“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.” Reuben Feffer, Along Came Polly

  1. Along Came Polly

Yes, Ben Stiller plays a risk analyst for life insurance who obsessively compiles lists about every possible risk in his life and in his relationships. But why we like this film has nothing to do with insurance. Instead it’s the character of Phillip Seymour Hoffman’s, Sandy. No matter what he is doing, be it giving relationship advice, leaving parties or playing basketball (let it rain!), Sandy is absolutely one hundred percent hilarious. 

  1. Double Indemnity

 Double Indemnity refers to the famous clause in certain life insurance policies that doubles the payout in accidental deaths. The film is adapted from the legendary novella by James M. Cain about an insurance salesman who falls for a married woman and agrees to kill her husband for a life insurance payout (and so they can be together). The story itself was inspired by a real life murder. In 1927 Ruth Snyder took out a $100,000 life insurance policy on her husband and, after unsuccessfully trying to kill him multiple times, turned to her lover, corset salesman Henry Gray who helped with the nefarious deed. You’ve got to watch out for those corset salesmen!