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Life Health > Life Insurance

25 best insurance movies: 6-10

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10. The Truman Show (1998)

Starring Jim CarreyEd HarrisLaura Linney

Directed by Peter Weir

What’s it about: An insurance salesman/adjuster discovers his entire life is actually a TV show.

Why watch it: Made in 1998, a few years before reality TV seemed to take over the media and our lives, The Truman Show is all the more frightening now, as its voyeuristic message has taken on a creepy realism through social media and Honey Boo Boo.

Interesting factoid: The Latin motto on the double archway in the Seahaven town center is UNUS PRO OMNIBUS, OMNES PRO UNO, translated to English as: “One for all, all for one,” thus fitting the premise of the show within The Truman Show.

Business takeaway: What is fact and what is fiction? What, in your life, is truly authentic? Those are the questions to ask yourself as you go through your day, sell products and cultivate relationships.

Memorable scene: The scene (in the video above), where Truman’s morning begins. The scene’s “payoff,” both literally and figuratively, is when the town’s twins push Truman against a product placement sign, giving us a moment that is both hilarious and terrifying.

Memorable quote:

Truman: Good morning, and in case I don’t see ya, good afternoon, good evening and good night!

Next up: Death of a Salesman


9. Death of a Salesman (TV 1985)

Starring Dustin HoffmanKate ReidJohn Malkovich 

Directed by Volker Schlöndorff

What’s it about: The Arthur Miller play comes to life in this made-for-TV version, also penned by Miller. It’s the classic tale of Willy Loman (Dustin Hoffman) a traveling insurance salesman who is slowly losing his mind and his will to live.

Why watch it: You might be familiar with the play, but Hoffman’s incendiary performance as Willy Loman makes it well worth another viewing.

Interesting factoid: It took three and a half hours for makeup artists to transform Dustin Hoffman, then in his forties, into Willy, who is described in the stage directions as “over sixty”.

Business takeaway: You are only as big as your dreams, but to realize those dreams you have to be willing to take the first step.

Memorable scene: Where Biff (John Malkovich) visits Willy at the hotel in Boston forever changing the direction of both of their lives.

Memorable quote: 

Biff Loman: [arguing with Willy] Pop, I’m a dime a dozen and so are you… 

Willy Loman: [shouting] I am not a dime a dozen! I’m Willy Loman and you are Biff Loman! 

Biff Loman: [to his father] Will you let me go, for Christ’s sake? Will you take that phony dream and burn it before something happens?

Next up: About Schmidt

8. About Schmidt (2002)

Starring Jack NicholsonHope DavisDermot Mulroney 

Directed by Alexander Payne

What’s it about: Upon retirement from the life insurance industry, Schmidt (Jack Nicholson), finds himself adrift and sets out on an existential quest, even if he wouldn’t call it that, to find purpose for this new chapter in his life.

Why watch it: Known for playing outlandish characters who take over the screen with bravado and charisma, Nicholson goes subtle and small in this performance and it’s his best work in decades.

Interesting factoid:  When Jack Nicholson met Alexander Payne to discuss his role, Payne had a one-sentence directive for him; it was “Jack, I want you to play a small man.”

Business takeaway: What if our life’s work was just that, work? Don’t wait until it’s too late to find you’re life’s purpose.

Memorable scene: The opening “wordless” sequence that tells us so much about Schmidt without ever uttering a word.

Memorable quote:

Warren Schmidt: Relatively soon, I will die. Maybe in 20 years, maybe tomorrow, it doesn’t matter. Once I am dead and everyone who knew me dies too, it will be as though I never existed. What difference has my life made to anyone? None that I can think of. None at all.

Next up: Groundhog Day

7. Groundhog Day (1993)

Starring Bill MurrayAndie MacDowellChris Elliott 

Directed by Harold Ramis

What’s it about: A cynical weatherman (Bill Murray), sent to cover the annual Groundhog Day, finds himself trapped living the same day over and over again.

Why watch it: If for no other reason, then do it for Ned Ryerson, Needle Nose Ned. He’d do it for you. Bing!

Interesting factoid: Bill Murray was bitten by the groundhog twice during shooting. Murray had to have anti-rabies injections because the bites were so severe.

Business takeaway: Live every day as if it’s the only one you have. Because, “today” it is the only time you’ll ever have this one.

Memorable scene: I love the ice sculpture set piece and any of the smarmy moments with Chris Elliott, but the interaction between Murray’s weatherman and insurance salesman Ned Ryerson are classic.

Memorable quote:

Ned: Do you have life insurance, Phil? Because if you do, you could always use a little more, right? I mean, who couldn’t? But you wanna know something? I got the feeling…


Ned: … you ain’t got any. Am I right or am I right? Or am I right? Am I right?

Next up: The Thomas Crown Affair

6. The Thomas Crown Affair (1968)

Starring Steve McQueenFaye DunawayPaul Burke

Directed by Norman Jewison

What’s it about: An international playboy has everything, or does he? Unfulfilled with living the good life, he turns to crime only to have a sexy insurance investigator (is that an oxymoron?) hot on his trail.

Why watch it: The interplay between Steve McQueen and Faye Dunaway is the reason why stars play out their characters’ lives on the big screen, and why we pay big bucks to go see them. Also, check out the remake with Pierce Brosnan and Renee Russo, it’s a rarity in film—a remake almost as good as the original.

Interesting factoid: The one-minute kissing sequence between the two leads took eight hours to film over a number of days.

Business takeaway: Be happy with what you have. If you’re bored being rich, start a foundation like Bill Gates.

Memorable scene: The chess match, which is about so much more than the match itself.

Memorable quote:

Sandy: You’re mad! Absolutely mad!

Thomas Crown: What else can we do on Sunday?

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