Okay, insurance probably isn’t the most glamorous topic on anyone’s list. It does, though, occasionally make its appearance on the big screen. Given the fact that I have spent pretty much all of my career in the industry, I enjoy movies that mention my favorite topic. Here is my list (not in any particular order) – I encourage anyone to add suggestions!
1. Double Indemnity (1944) The plot: Los Angeles insurance agent Walter Neff (Fred MacMurray) falls under the spell of Phyllis (Barbara Stanwyck), the seductive wife of a client. Together, they trick her husband into signing a life insurance policy then orchestrate his death to look like an accident, so Phyllis will collect twice under the double indemnity clause. Just one catch: Neff’s mentor Barton Keyes (Edward G. Robinson), the insurance company’s claims adjuster, smells foul play.
2. Groundhog Day (1993) The plot: TV weatherman Phil Connors (Bill Murray) loathes his annual obligation to cover the emergence of Punxsutawney Phil from its Pennsylvania burrow every Groundhog Day. Unfortunately, the fates decree he’ll experience the same Feb. 2 again and again until he gets it right with the help of his news producer Rita (Andie MacDowell).
3. Cedar Rapids (2011) The plot: Small-town Iowa insurance agent Tim Lippe (Ed Helms) winds up in “Hangover” territory when he’s dispatched to a regional insurance conference in the “metropolis” of Cedar Rapids. Lippe’s assignment: Bring home the coveted Two Diamond award previously won by a senior partner who recently hanged himself. Insurance veterans Dean Ziegler (John C. Reilly) and Joan Ostrowski-Fox (Anne Heche) do the corrupting, but it’s Lippe who clings to his principles and ultimately prevails, redeeming himself and the entire insurance profession.
4. The Apartment (1960) The plot: Lonely bachelor C.C. “Bud” Baxter (Jack Lemmon) works long days at a New York insurance company but spends longer nights pacing the streets of Manhattan while his superiors use his apartment for trysts. Baxter quickly rises up the corporate ladder to become assistant to head honcho Jeff Sheldrake (Fred MacMurray). But when Baxter learns Sheldrake has been using his digs to entertain Fran (Shirley MacLaine), the elevator operator with whom Bud is smitten, things get complicated.
5. A Little Trip to Heaven (2005) The plot: Forrest Whitaker plays an insurance adjuster who discovers what may possibly be a couple engaged in identity theft, murder, and life insurance scams.  His job is to uncover any fraudulent activity and protect the company’s investment.  In at least three separate scenes, he is shown in his office negotiating a payout with the beneficiaries.  On all three occasions, he is able to provide evidence of why their claim is not valid, and offers them a substantially lower payout.
6. Along Came Polly (2004) The Plot: Risk analyst Reuben Feffer (Ben Stiller) loses his wife (Debra Messing) on their honeymoon when he discovers her being intimate with a scuba instructor (Hank Azaria). When he returns home, Reuben’s friend and coworkers try to cheer him up and take him out to meet new people. He has a chance encounter with middle school classmate Polly Prince. The movie then follows the dating of Reuben and Polly (Jennifer Aniston), he risk-avoider and she a free spirited wanderer. When Lisa, Reuben’s wife, returns from her fling with Claude Reuben must choose to take back his cold-hearted wife or run with the commitment-fearing Polly
7. The Fortune Cookie (1966) The Plot: A cameraman (Jack Lemmon) gets injured by a football player during a game and goes to the hospital. There, his cunning brother in law who happens to be a lawyer (Walter Matthau) convinces him to pretend that his legs have been paralyzed. This way, they can receive a huge indemnity from the insurance company. Of course, the insurance company’s men suspect that the paralysis is a fake one, and so a big “game” begins. The first collaboration of the successful team of Walter Matthau and Jack Lemmon.
8. About Schmidt (2002) The Plot: Warren Schmidt (Jack Nicholson) has led a safe, predictable life working in the insurance industry in Omaha, Nebr. for many years, yet now faces retirement. At the same time he is forced to take a hard look at his wife, his life and his relationship with his estranged daughter. An often hilarious series of events follow as Schmidt embarks on an unpredictable RV journey to attend his daughter’s wedding in Denver.
9. The Big White (2005) The Plot: This movie is about an insurance fraud scheme conjured up by travel agent, Paul Barnell.  When he finds a dead body in the snow of the Alaskan mountains, he tries to play it off as though it is the body of his missing brother, and collect the proceeds of his $1 Million life insurance policy.  This is another case of where the one committing fraud almost gets away with it, since he fools everyone, but then the insurance claims adjuster comes in and figures it out.
10. Alias Jessie James (1959) The Plot: This is a Bob Hope western comedy where Hope’s character, a life insurance agent, sells a $100,000 policy to outlaw Jesse James, who writes T.J. James on his application.  Jesse James describes himself as “well known in the banking and railroad industries”.  When Hope’s boss finds out, he is charged in finding Jesse James to return the policy to him, and help protect James before anything happens to him.