The Family Man

This is my seventh favorite holiday movie.

The Family Man is a cute little tale of "What If". Jack is a high-powered, uattached, wall street guy running a major corporation. He "has everything" but love. The movie opens with him saying goodbye to his long-time girlfriend, Tea' Leoni. He is headed off to England for a year internship with a financial firm. He ends up never seeing her again. 12 years pass and he gets a call from her at his office. He doesn't return the call but rather leaves work, stops a convenience store where he meets his "angel" Don Cheadle who is a punk with a winning lotto ticket. Jack intervenes when a gun is pulled on the cashier. Don ends up giving Jack a "glimpse" into what his life would have been like with the old girlfriend. It takes him to suburban New Jersey life with two kids, working at his father-in-laws tire store. It is a fun tale of seeing two sides of life.

here is another take from someone on Amazon written much better than mine.

Jack Campbell (Nicolas Cage) is the quintessential Wall Street shark, scoring killer deals by day and shallow escort sex by night. His round-the-clock routine of empty luxuries is disturbed one lonely Christmas Eve when a gun-packing punk (Don Cheadle)--perhaps an angel of mercy--responds to an altruistic gesture from Jack by giving him "a glimpse" of the life he could have had. Could have, that is, if he had married the girlfriend (Téa Leoni) he'd abandoned 13 years earlier, raised two adorable children, worked in his father-in-law's retail tire outlet, and lived happily ever after in suburban New Jersey. Thrust into this "glimpse" of the path not taken, Jack's a single-malt man in a lite-brew world, wondering if he'll ever return to his "better" life of callous wealth and solitude--or if he even wants to.
Carp all you want about this derivative premise, with its marginal stereotypes and biased embrace of domestic bliss and dirty diapers. The simple fact is, The Family Man works like a charm. Under the assured direction of Brett Ratner (Rush Hour), this holiday crowd-pleaser offers comedy and chemistry in equal measure, making the hilarity of Jack's predicament a smooth catalyst for that rarest of movie romances: the marital love story. Leoni is Cage's perfect match as Jack's idealized but imperfect wife, and the movie's appeal largely derives from its awareness that any life has its pleasures and pains. While it only flirts with the dark desperation that makes It's a Wonderful Life a classic predecessor, The Family Man is an irresistible what-if fantasy, and even its debatable ending rides on a wave of genuine warmth and sentiment. --Jeff Shannon