The Living Room Small Business Film Festival

It’s that time of year again. The holidays, you say? Nope, that’s not what I am referring to. The shopping season? True, but no. Your store’s busy time of year? Yes, well, it may be that, but no, that’s not what I am talking about either.

The Godfather is, I submit, the ultimate holiday, small business fare

No, it’s movie time my friends, on two fronts: First, as we all know, this is the time of year when the studios offer up their best movies of the year – the Oscar bait. It’s also the time when a lot of us curl up on the couch with throws and pillows and catch up on some movies with family and friends.

In another life, I might have been a movie reviewer, and so we will indulge this fantasy this week as I share my choices for this first-ever edition of the Ask an Expert Entrepreneurship Film Festival. So go ahead – put on your jammies, call the family into the den, pop some popcorn, and check out these great flicks, all of which have some sort of small business or entrepreneurship angle (however tenuous or remote!)

It’s a Wonderful Life: Really Steve, you are going to kick off your inaugural film festival with this tired old shoe? You bet, because what is George Bailey if not a struggling small businessperson?

That dusty old building and loan of his sure doesn’t make him much money, and indeed is the cause of a lot of stress, but what he (and we) learn in the process is that, as with many small businesses, it allows the owner to help himself and others along the way, warts and all.

And anyway, if I didn’t pick It’s a Wonderful Life, I wouldn’t be able to tell you to re-watch that scene where George and Mary are on the phone together. Wow.

Love Actually:My family’s favorite holiday movie, this modern classic really shows quite well the central role work plays in our emotional lives. On one end, we have the great scene where Mr. Bean is so strangely wrapping a gift at a department store in London. On the other end, we also get to see the problems that arise with workplace romances, even if you are the Prime Minister. And as an added bonus there is nothing better than Bill Nighy as the old, not-quite-washed-up old rocker, Billy Mack.

Risky Business: We’re coming in now back-to-back with Tom Cruise movies. Risky Business was one of Cruise’s first movies, and still one of his best. Hijinks ensue when his “Future Enterprises” project goes amuck and he opens a brothel in his parent’s house while they are away for the weekend.

Magnolia: Veering away from the light fare now, consider a movie Cruise did many years later with director Paul Thomas Anderson and the late, great Phillip Seymour Hoffman (among many others in this fantastic ensemble.) Cruise plays a misogynistic TV huckster/guru/entrepreneur. And Julianne Moore was incredible.

The Godfather: This is, I submit, the ultimate holiday, small business fare. After all, The Corleones are nothing if not a family business, with its attendant ups and downs and having to deal with one’s loved ones, even if you don’t want to (we’re talking to you, Fredo.)

And in any case, as Tom Hanks later says in a different movie (You’ve Got Mail) “all of life’s questions are answered in the Godfather, for instance, “What to pack for my summer vacation? ‘Leave the gun, take the cannolis.’”

Casablanca: The greatest movie of all time is also a classic small business tale. Rick’s Café American is a beloved local institution with a proprietor who doesn’t love what he is doing anymore. Little did we know it would take Ilsa and Victor Lazlo blowing into town to bring about that change.

And our friend Rick? He’s not in it for the money, that’s for sure. Why? Because some fundamental things apply as time goes by . . .

Like watching great movies in December.