Last Updated on December 29, 2023

Who would have thought that one of the more enduring family movies in the last 20 years would come from Brett Ratner and star Nicolas Cage? Indeed, The Family Man was only a modest success when it came out over the holiday season in 2000, but it has since inspired rip-offs and remakes and is a beloved classic for many of us.

In it, Nicolas Cage plays a high-flying businessman named Jack Campbell, who doesn’t appreciate the little things in life, such as Christmas. It’s lonely at the top, but he consoles himself with his Ferrari, penthouse apartment in New York, and hook-ups with women such as supermodel Amber Valletta, who has a small role as his bedmate early in the film. Yet, being alone on Christmas Eve, he does a good deed when he intervenes in a convenience store standoff by showing empathy towards a wired, gun-toting customer, played by Don Cheadle, Jack’s guardian angel. Knowing that despite his cold exterior, there’s a kind man buried within Jack, he gives him a “glimpse” of what could have been. You see, thirteen years ago, Jack decided to take a prestigious internship in London rather than stay behind in New York with his college sweetheart, Kate, played by Tea Leoni. In his “glimpse,” he sees what life would have been like had he settled down with Kate into a middle-class life in New Jersey, where the two have a happy suburban life as the parents of two adorable children.

At first, Jack is horrified to discover his lot in life, which includes a job working as a manager for his father-in-law’s tire dealership, but eventually realizes there’s more to life than just money.

When I saw The Family Man in 2000, I was about 18 years old and didn’t think much of it. I thought it was a cheesy comedy, and I became fixated on the movie’s theme: ambition is evil. I didn’t get the message that Jack and Kate, for some reason, had to choose between their ambitions and the idea of having a family life. To me, they could have done both.

Then I grew up.

Twenty years later, the film plays as much more bittersweet, with it being a sweet story about a man with regrets who gets a glimpse at what his life might have been had he taken another path. I don’t think any of us, at this point, ever doesn’t wonder what life might have been like had we made different choices. What would have happened had I taken – or not taken – a specific job? How about that relationship I let end? What would have happened had I fought for it? Would I be better off? Would I be miserable?

To be sure, The Family Guy does perhaps portray the life Jack didn’t choose too rosey. Being a suburban dad with a job you don’t like isn’t the easiest thing in the world, and the movie is flawed in portraying Jack and Kate’s life together as impossibly idyllic. After 13 years together, they’re shown to still be head over heels in love, with Leon’s Kate an angelic character seemingly without any ambition beyond her family.

Yet, no one can deny that the movie works, with the casting for this particularly on-point. While many of us look at Nicolas Cage now as a loveable eccentric, he’s recently said he gets frustrated getting cast in heavy films and wishes someone would allow him to be funny again. Indeed, he did a few lovely comedies in the late nineties/ early 2000s, including Honeymoon in Vegas, Guarding Tess, Trapped in Paradise, and this one. He is terrific at being soulful and vulnerable, and it’s utterly convincing both as the hard-driving businessman Jack and the softened family man he becomes. When his glimpse ends, it’s heartbreaking, with Cage conveying a palpable sense of loss. Tea Leoni, his dream wife, matches him, and she is so likable and sweet that I’m surprised she never became a more prominent name in movies.

While Brett Ratner is somewhat despised and cancelled now thanks to his offscreen behaviour and a slew of terrible movies, The Family Man is by far his best movie outside of the first two Rush Hour films. He maybe packs on the schmaltz a bit too much, but he surrounds Cage with a top-shelf supporting cast, including the also cancelled Jeremy Piven as his best friend and neighbour, a young Kate Walsh, Mary Beth Hurt, Saul Rubinek, Harve Presnell and many more. Plus, Don Cheadle is his guardian angel. It also has a soothing score by Danny Elfman and some fun needle drops, especially Chris Issak’s Wicked Game, which, of course, was the theme song to one of Cage’s best films, Wild at Heart.

The only bad thing you can say about The Family Man is that it’s unoriginal, with the film not only a riff on A Christmas Carol but also closely patterned on the largely unseen James Belushi film Mr. Destiny. Perhaps it’s fitting that The Family Man was ripped off quite a bit in the following years, with Kevin Sorbo doing a Christian rip-off called What If, while the film was recently remade in South Korea as Switch. When it first came out, The Family Man broke even, grossing $120 million worldwide on a $60 million budget, but it’s become a perennially Christmas favourite. Indeed, it’s a sweet little movie worth revisiting, particularly if you want to see Cage’s kinder, gentler side.