There was a time when "T2: Rise of the Machines" would be on TV and I’d stop whatever I was doing to watch it.

I remember sitting down with a family near the Arctic Circle in Sweden to see the film, and “T2” in Swedish with English subtitles was a trip. Everyone was mesmerized. “The Matrix” was like that for a while as well, and I’m guesstimating I’ve seen “Star Wars” and “The Empire Strikes Back” at least 10 times apiece.

OK, maybe 50 times apiece.

When I was going through my divorce I heavily rotated through “Forgetting Sarah Marshall,” “Knocked Up” and “Role Models.” (FYI… the recently divorced should limit their viewing of “Saving Private Ryan” to no more than once a week.)

Why do we do it? Why do we watch some movies as many times as we can?

Is it because of the sheer quality of the story telling? The action? Or maybe it speaks to something deeper inside of us? Kids like to hear the same story over and over again, and we’ve been looking at the Mona Lisa since 1508. Some 500 years later we’re still interested, so there must be something going on.

Here are the movies I can’t stop re-watching, and more importantly why …

  1. “Fight Club” — There’s something magical about “Fight Club,” and I’m going to talk about it: Brilliant actors (Edward Norton, Brad Pitt and Helena Bonham Carter) coming together with a director who has strong music video sensibilities (David Fincher). and source material from a hell of a good writer (Chuck Palahniuk) and it works beautifully. There are scenes that mesmerize me, sure, like the “start a fight and lose it on purpose” sequence, and the discussion of who’d you most like to fight, to the sex scene, which is part music video and part phantasm, to “I’m Jack’s raging bile duct!” But it’s deeper than that. This movie is a meditation on how a fear of death churns consumerism. How advertising plays on our must vulnerable sensibilities and how aggression and sex are connected. The ultimate hook for me, though, is the end: the pre “9/11” and “99 percent” connection to blowing up buildings and taking down the banks. They say that a really good poet will be about 500 years ahead of their time; Palahniuk and Project Mayhem were about a decade ahead.
  2. Casablanca” — So much has been written about “Casablanca” that there’s no need to cover the same ground here, but this movie is a testament to the unexpected in film making. The chemistry between Humphrey Bogart and Ingrid Bergman is the kind that can’t be manufactured. Most of us will experience some form of unrequited love in our lifetime (if you haven’t you probably don’t get why people love this movie). but once you have, the movie is forever unlocked and you know just how Rick feels when Ilsa walks into that bar and he says, “Of all the gin joints in all the towns in all the world, she walks into mine.” Exactly!
  3. “Aliens” — If you work for a large organization, then you understand there’s a difference between formal authority and leadership. You probably have experienced a “Gorman” who’s gumming up the works. Besides incompetent senior leadership, this movie is also about the differences between kinds of courage. No doubt that many of the Marines in this movie are courageous, but it’s nothing when compared to Newt’s courage in the face of overwhelming odds. This movie is actually one of the best war films ever made, it’s just disguised as a Science Fiction-Horror. “Aliens” accurately captures the challenge of compromised and conflicted missions, greed versus loyalty, and it’s also an amazing retelling of Beowulf. It’s a heck of a lot of fun.
  4. “The Caine Mutiny” — Like “L.A. Confidential” and “Pale Rider,” this movie is about what it takes to be a good man and the kind of men you’ll meet in the world. Fred MacMurray is perfect as the passive-aggressive mealymouthed fuckstick Lt. Tom Keefer, the kind of guy who can ruin your career with a lot of unnecessary drama, and it’s the confrontation at the end between Keefer and Lt. Steve Maryk (Jose Ferrer) that makes this movie so watchable. It’s five minutes of perfect execution. Yes, Humphrey Bogart is awesome as Lt. Cmdr. Philip Francis Queeg, but it’s that central conflict between Keefer and Maryk that makes this movie work. I ran into a “Tom Keefer” like character in my career and the verbal confrontation, a breathtaking honesty, more than a physical confrontation that I clambered for. Let’s face it, we love it when people are called on their shit in movies because it so rarely happens in real life.
  5. “The Devil Wears Prada” — This is one of the best business movies ever made. Underneath the clothes and endless talk of fashion, this is a wickedly sharp movie about competence and accountability. Meryl Streep is brilliant, but it’s the journey of Anne Hathaway’s Andy Sachs that makes this movie almost a Harvard business case. She loses her friends and her boyfriend, not because she’s consumed by the job, or because Miranda Priestly is the devil, but rather because she’s tired of their excuses for mediocrity. It’s like she’s been hanging with the boys from “Glenngarry Glen Ross” and earns her way to Alec Baldwin and Mitch and Murray. This is the antithesis of a movie like “Pretty Woman,” in that Andy actually earns her wish fulfillment through competence and commitment versus having it “given” to her because she’s beautiful. This is a very positive business movie and a very positive movie about women and leadership.

Bonus …

  1. “The Counselor” — HBO has had this box office bust in heavy rotation for what seems like six months. Every time I turn the TV on, “The Counselor” is on, and I watch it. I can’t help it. It’s not like a car crash that you can’t look away from, it’s more like an awful odor that for some reason you’re compelled to smell twice. This movies stinks, really stinks, but in a delicious way. It has everything going for it, great actors (Brad Pitt, Cameron Diaz, Penelope Cruz, Michael Fassbender, Javier Barem, even Rosie Perez and Ruben Blades) and an amazing writer and director in Cormac McCarthy and Ridley Scott, respectively, but yet it still sucks. Unlike “Fight Club” or “Casablanca,” all the elements didn’t work together, and it’s a fucking mess of a movie. Yet I love it. It’s so close to being great, and Diaz could be an amazing villain, but close only works in hand grenades and horseshoes, not major motion pictures.