Delivery Man is one of those movies that pushes all of the right buttons when you're watching in a dark theater with a bucket of popcorn in your lap. It works on a surface level and gives you the impression of an entertaining experience. I even teared up a couple of times, right when I was supposed to. And then, on the walk home, I started to see holes in the plot, and how most of what happens in the movie is totally convenient, and that the tone is actually pretty off key. At least the disappointment takes awhile to kick in.
Based on the Canadian film Starbuck, Delivery Man is the story of David Wozniak (Vince Vaughn), a delivery driver for his family's meat shop and perennial ne'er do well. He owes money to all sorts of shady characters, is growing pot to supplement his income, and has just discovered that his girlfriend Emma (Cobie Smulders) is pregnant. At this point, "girlfriend" is almost a stretch of the word, given the fact that their relationship is totally lacking in communication and real intimacy. Though reluctant to kick David to the curb, Emma wants him to straighten up and get a life.
Conveniently, a lawyer from a sperm bank David used to visit is waiting when he returns home from learning he's going to be a father. It turns out that David's, er, deposits (left under the name Starbuck) were used to father 533 children and 142 of them would like to know his identity. This is stunning news, and the lawyer leaves David with a packet containing the identities of the children who hope to find him.
Overcome by curiosity, David tracks down a kid (now about twenty years old) and sees a full-fledged human being walking around with his genes. The experience inspires him to track down more of his offspring, never revealing his identity, but striking up conversations, offering impromptu advice or support, and generally acting as a guardian angel. The process takes David outside of himself and begins shaping him into a responsible adult. Meanwhile, David attempts to rebuild his relationship with Emma (a smart, stable police officer) without ever mentioning any of this Starbuck business to her. "Oh, by the way, I fathered 533 kids and in my free time, I try to meet them. Also, there's kind of a huge lawsuit going on." A secret this size doesn't bode well for the future of their relationship, but when he finally drops the bombshell, she processes fifty or sixty conflicting emotions in a span of about thirty seconds, then most likely lives happily ever after.
The point of the movie, presumably, is to show David's evolution as a person through the experience of identifying as a father. It's a decent premise that lends itself to plenty of sweet moments, but the entire movie is far too dependent upon coincidence and many scenes defy credibility. David learns Emma is pregnant immediately after his brother tells him he really ought to have a kid. He happens to meet one of his children by pretending to be the pizza man while she happens to have a drug overdose in her bedroom. He shows up to visit his girlfriend just as an ambulance pulls up in front of her apartment. Basically, David has magical timing, but after awhile you're bound to start rolling your eyes. This sort of plotting works in a typical Vince Vaughn comedy, but most of the movie plays like a drama and Vaughn's faithful wing man Owen Wilson is nowhere in sight.