These are my recommendations for films and movies similar to The Family Man. Keep in mind that this list is in no particular order.
Young Chuck Norstadt (Nick Stahl) wants nothing more than to join a prestigious military academy like his late father, but he is wary of the school’s lofty academic standards. With only a single summer in which to study for the entrance exam, Chuck finds an unlikely tutor in the form of Justin McLeod (Mel Gibson), a disfigured recluse who was once a teacher. McLeod agrees to teach Chuck, and the two form a deep friendship — until Chuck learns of the secret behind McLeod’s terrible scars.
When successful child psychologist and one-time playboy Samuel Faulkner (Hugh Grant) hears that his girlfriend, Rebecca (Julianne Moore), is pregnant, he panics. As Faulkner’s crippling fear of commitment sets in, Rebecca decides to leave him. Realizing he wants to spend his life with her, Faulkner struggles to come to terms with the gravity of impending fatherhood — a struggle helped in no way by the antics of Rebecca’s bumbling obstetrician, Eastern-Bloc refugee Dr. Kosevich (Robin Williams).
Best friends since they were kids, Rabbi Jacob Schram (Ben Stiller) and Father Brian Finn (Edward Norton) are dynamic and popular young men living and working on New York’s Upper West Side. When Anna Reilly (Jenna Elfman), once their childhood friend and now grown into a beautiful corporate executive, suddenly returns to the city, she reenters Jake and Brian’s lives and hearts with a vengeance. Sparks fly and an unusual and complicated love triangle ensues.
When a loved one dies, are they gone forever? As head of emergency services for Chicago Memorial Hospital, Dr. Joe Darrow (Kevin Costner) is a respected expert in trauma and triage. But his professional knowledge provides little comfort when tragedy claims the life of his wife. A doctor herself, Emily Darrow (Susanna Thompson) was on a medical mercy mission when she died in a bus accident on a remote mountain road in Venezuela. Joe starts believing his wife is trying to communicate with him.
While on her deathbed, the rich Edwina Cutwater (Lily Tomlin) has her lawyer Roger Cobb (Steve Martin) add the odd stipulation to her will that her soul will be inherited by the young Terry Hoskins (Victoria Tennant). The plan backfires when Edwina dies. She ends up inhabiting Roger’s body and controlling only its right side. Edwina and Roger are forced to work together to find a way to get her soul out his body and into the body she originally intended.
With little time left due to a terminal disease, Henry Poole (Luke Wilson) buys a cookie-cutter house in a Los Angeles suburb and waits peacefully to die. However, he starts hearing a voice from next door that seems to be mimicking him perfectly. Upon investigating, Henry discovers that it’s his neighbor’s mute daughter with a tape recorder. Meanwhile, his other neighbor, Esperanza (Adriana Barraza), believes a stain on Henry’s patio is the face of Jesus and begins showing it off to people.
After his true love (Isabel Glasser) falls in a coma, test pilot Daniel McCormick (Mel Gibson) undergoes suspended animation in a military experiment conducted by his friend Harry Finley (George Wendt), supposed to last a year. A series of mishaps result in McCormick’s being all but forgotten and, 53 years later, a young boy (Elijah Wood) accidentally frees a confused McCormick, who eventually lives with him and his mother (Jamie Lee Curtis). However, complications arise from the experiment.
Catherine Boyd (Meg Ryan) is a highly intelligent doctoral student at Princeton University and is engaged to stuffy Professor James Moreland (Stephen Fry). Ed Walters (Tim Robbins), a mechanic and all-around regular guy, falls for Catherine and searches for a way to impress her. Believing that the key to Catherine’s heart is his IQ, Ed passes himself off as a physicist with the help of Catherine’s uncle, who just happens to be Albert Einstein (Walter Matthau).
Architect Newton Davis (Steve Martin) is distraught when his girlfriend, Becky (Dana Delany), spurns his proposal and refuses to move into the lavish house he designed for her. Davis, who cannot imagine himself living alone in the house, shares his tale of woe with Gwen (Goldie Hawn), a dishonest waitress he thinks doesn’t speak English. Complications arise when Davis, on the brink of reconciliation with Becky, discovers that Gwen has moved into the couple’s soon-to-be dream home.
Three months after a one-night stand with Isabel Fuentes (Salma Hayek) in Las Vegas, New York City real estate developer Alex Whitman (Matthew Perry) learns she is pregnant. Despite being a terminal bachelor, Alex is drawn to Isabel, and the pair marries. Isabel’s father, Miguel (Tomas Milian), suspects Alex has bad intentions, and the couple finds themselves pressured by both their families. When Alex is offered a promotion, he is torn between his new life in Las Vegas and success in New York.