The Family Man (2000)

Synopsis
In this whimsical romantic comedy that recalls It's a Wonderful Life, Nicolas Cage plays Jack Campbell, a workaholic bachelor who gets to see what his life might have been like had he stayed with his old sweetheart, Kate (Tea Leoni). Thirteen years before, Jack accepted a brokerage internship that marred his relationship with Kate, under the promise that they would only be separated one year. But much later, Jack has become an urban Wall Street exec with no wife or family of his own, and a mysterious proxy (Don Cheadle) offers him the opportunity to step into the life he left behind. After falling asleep in his posh New York apartment, Jack awakens to find himself in bed with his now-wife Kate, daughter Annie (Makenzie Vega), and a new baby, none of which he has ever experienced in his fast-paced single life. After discovering his "real" life has been eliminated, he begrudgingly tries to fit in with his newly appointed life as a family man. The Family Man also stars Saul Rubinek and Jeremy Piven. ~ Jason Clark, All Movie Guide