Here is a short list of movies that I have found to be both entertaining and highly instructive. Each of these films has, in a way, shaped my personal philosophies. In other words, take pains to avoid these movies, lest you wish to risk expanding your horizons and becoming a more interesting person.

In no particular order:

1) The Godfather Everybody should be required to watch The Godfather on an annual basis. All the basic lessons of life are in there. In order to reinforce, supplement, or–if necessary–counteract those lessons you learned from your father, watch this movie once a year. Probably the most important lesson of the movie is: Don’t be afraid to use power, but always use power wisely, and only after you’ve made certain that it won’t come back to bite you. (Just ask Sonny.)

1, Part II) The Godfather, Part II — Really, this is more of the same lesson, “all growed up.” The dual plot lines of Michael and young Vito are revealing; in both cases, the protagonist amassing power by insisting on dealing with the world as it is, not as they think should be.

2) Office Space — Riiiight… I’m going to have to go ahead and… award extra credit… to anyone who’se got a red Swingline handy. More than a classic, this movie holds a lot of secrets about what’s wrong in business today, and how to make it better. Most overlooked lesson of the film: Life’s a lot more fun if you’re friends with an Indian rap aficcionado.

3) Parenthood — A Ron Howard movie with an all star cast, led by Steve Martin. I always thought this movie was “fine,“ until I caught it on cable about three months after my second daughter was born. Words like “prophetic,” “critical,” “important life lessons,” and “Wow, them, too?” suddenly flashed through my mind. Important lesson: The roller coaster never ends; chase your goals, but make sure you learn to enjoy the ride, because–like Jason Robards says–it never ends.

4) Dawn Patrol (1938 version) — watch what happens when a war aviator goes from flying ace to man-in-charge. Not only an indictment against war, it’s also a perfect representation on how friendships can become impacted after one gets promoted.

5) Patton — Leadership, politics, and charisma, with a dash of mysticism. And if that opening speech in front of the American flag isn’t one of the greatest motivational speeches of all time, I don’t know what is.

6) His Girl Friday — The power of interpersonal influence, at hyperspeed; also, it’s fun to watch two incredibly quick-witted people try to outmaneuver one another for a full 92 minutes.

7) Rocky — This could be the most perfect movie ever made. The sequence before the big fight is one of the best on film… the subtleties of Rocky’s interaction with the promoter (who says ”I’m sure you’ll give us a great show“ instead of ”great fight“) and Rocky’s subsequent realization that to “win,” he has to go the distance against Apollo Creed–that he can’t knock out the champ even if he has the opportunity, because he has to go the distance!–went completely missed by me the first few dozen times I saw the movie. But in that 9 minute sequence, when Rocky strips his world down to a single decision and then comes to a conclusion to move forward even in the face of overwhelming odds–despite having an easy road out of danger (all he has to do is take a dive!)–Stallone gives us a window into true courage. In life, when a leader faces a tough call, he or she closes the door, forgets the world, and tries to face the decision alone… no past, no consequences, no nothing, except what’s right. It’s a feeling we all know, a moment that tests us to the core. And Stallone captured it.
The 6th Sense — Perception is everything… this is storytelling at its best. This movie offers a powerful lesson in how the process of revealing information can color the information itself.

9) When We Were Kings — The power of personality, the power of the press, and the power of power: Ali does all he can to win this fight before he ever steps into the ring. Why? When you see what Foreman does to the punching bag in the training room, you’ll know.

10) The Princess Bride — Good triumphs over evil, true love transcends death, and Billy Crystal crows, ”To blave…“ Who can argue with any of that? Plus, this movie correctly shows how people bring their own quirks into their official roles: take Inigo Montoya, who is on a lifelong mission to avenge his father, but who also works for Vencini ”to pay the bills.“ We often want people to leave ”themselves“ at home when they are acting in an official capacity, yet watch how refreshing it is to see these characters’ honesty!

11) Gladiator — In the end, it’s Excellence & Courage in one corner, and Cowardice & Cunning in the other… as it so often is in life. And as in life, Excellence & Courage eventually wins, but only after paying a steep price for a victory that was inevitable from the start. The subtext of this movie for me is this: it doesn’t matter what twists and turns life throws at you, you somehow manage to wind up right back where you’re supposed to be, right when you’re supposed to be there. This movie reminds me an Alexander Pope quote: ”Whatever is, is right.“

12) Shawshank Redemption — This movie is about one thing: the power of the human spirit.

13) 12 Angry Men — Few movies offer better character studies than this one; this movie is frequently used in organizational behavior classes to help show common group dynamics and how to overcome them.

14) High Noon — Gary Cooper is the epitome of the stand up guy in this movie, but notice how the lone cowboy spends the entire movie trying to recruit help… at no point does he ever want to shoulder the burden of facing the outlaws by himself. (Designers of American pop culture kind of missed that point when idealizing Cooper’s Will Cain character.) Also, watch the scene in the church for a perfect representation of how cowardice can twisted to sound rational in a group setting.

15) On the Waterfront — Most people think of courage as having the guts to make big, bold moves. Here’s what real courage looks like; the tough conversations, the dirty looks, the tortured souls… the beatings, emotional and otherwise.

16) The Usual Suspects — Before there was M. Night Shyamalan, there was The Usual Suspects. One of the best plot twists I’ve ever seen… and a great story within a story. (It helps that when I saw it the second time, at the Vic in Chicago, it was the first half of a double feature and was followed by Ferris Bueller’s Day Off. What a crowd that was…)

17) Dr. Strangelove… — Worth watching for the scenes in the War Room alone. The conversation between George C. Scott and Peter Sellers about the merits of a pre-emptive strike (”I’m not saying we wouldn’t get our hair mussed!“) should be shown in every ethics class out there. The scene is as hilarious as it is appalling.

18) Die Hard — Because everyone needs an escape from reality once in awhile.

19) Raiders of the Lost Ark — For the contrast between the get-it-done guy (Indiana), who is in it for the love of the work, and the make-it-look-good guy (Belloq), who is in it for the spoils.

20) American History X — What makes change hard is that not only do you have to change, but the people around you also have to agree to accept the new you. This is easier said than done, especially when the change you make for yourself is to release the very weakness or vice (in this case, hatred) that defined your bond with others. For this reason, no change is without its price. By the way, the quote at the end is by Abraham Lincoln; it was the closing to his first inaugural address, and the topic to which he was referring was the South’s attempt to secede from the Union.

Posted under Self-Development, Lists, Leadership