Dan and Carter cross paths when business mega mogul Teddy K (Malcolm McDowell), Carter's boss, decides to buy Dan's company, Sports America. Dan is instantly demoted and on the verge of being fired. If pressure from his job wasn't enough stress, he discovers that same day that his wife (Marg Helgenberger) is unexpectedly pregnant and that his daughter, Alex (Scarlett Johansson), has her heart set on transferring from a state school to New York University.
Teddy K gives Carter Dan's old job at Sports America. Carter, who promises to be the company's "ninja assassin," is more than pleased by his raise and (Dan's) corner office. In his excitement over receiving the job, Carter even buys-and wrecks-a Porsche in hours. However, his confidence takes a beating after only a few days in the office, since he has no idea how to sell ads. His previous success stemmed from selling cell phones to kids and pretending to know what he was talking about. Carter may want to climb the corporate ladder, but it's obvious that he has too much heart. He reluctantly fires numerous employees, including two men that Dan had hired. One of the men, played by David Paymer, does an incredible job of showing his grief.
Carter is urged to "let go" of Dan because he's seen as a dinosaur. His salary is too high and his methods are too old. Carter does everything in his power to ensure that Dan stays put as his "wingman" because Carter knows that he needs Dan. Dan, meanwhile, would love nothing more than to quit, but how can he? He has just taken out a second mortgage on his house, has one daughter in college, another daughter in braces and a third child on the way. Things become still more complicated when Carter and Dan's eldest daughter, Alex, begin to date.
The reason this film succeeds is that the story is endearing without being sappy and fairly realistic without leaving the audience upset. The more alone Carter feels, the more time he tries to spend with Dan, and the more time Carter spends with Dan, the more Carter wishes he could be like his employee. We learn quickly that the family Carter grew up in was less than stellar compared to Dan's imperfect but loving home. Carter is truly a lost soul but at least he isn't alone anymore.
Corporate corruption and dedication to ruthlessness are the perfect backdrop for the movie. Instead of using political nemeses, writer Paul Weitz ("American Pie," "About a Boy") uses something much more real and easier to relate to in today's age of mergers and greed. The corporation's immorality allows us to see the honesty of the characters, and Weitz succeeds in creating very likable ones. Quaid and Johansson are in their element. Their roles are far from challenging, but they fit them perfectly nevertheless. This film may, however, hold a breakthrough role for Topher Grace. He truly makes many of the movie's scenes outstanding ones; his comedic timing is impeccable. This dramedy is heartfelt but light-it's good entertainment, without a doubt.