Ray Gleason (Danson) is an ex-convict trying to turn over a new leaf by opening a bakery. Lacking funds for his new venture, he plans to steal some valuable rare coins with his two bumbling criminal buddies Bobby (Saul Rubinek) and Carl (Gailard Sartain). They successfully pull off the heist, but Ray's estranged 11-year-old son Timmy (Culkin) then shows up unexpectedly. Being a lot cleverer than Ray and his cronies, Timmy soon finds out about the robbery, hides the stolen coins, and will only return them on condition that Ray spends time with him doing fun things.
So Timmy and Ray spend a week visiting an array of zoos, theme parks, aquariums and sporting events. Carl and Bobby tag along as well, just in case Timmy tells Ray where the loot is. Inevitably, father and son grow to like each other. Meanwhile, Timmy discovers that the police are closing in on his dad and Ray falls for Theresa (Glenne Headly), unaware that she is the undercover cop trailing him. Sensing that Ray will be caught, Timmy urges his dad to choose between him and the coins.
This film provides examples of:
- Adults Are Useless: Timmy easily outsmarts almost every adult in the movie.
- Ambiguously Christian: Carl gives the sign of the cross before going down a debris chute to escape but doesn't show any signs of being Christian otherwise.
- Awkward Father-Son Bonding Activity: Inverted, as the activities are done at Timmy's behest to improve their relationship.
- Blackmail: Timmy hides the stolen coins and will only return them if Ray spends a week showing him around San Francisco.
- Friend-or-Idol Decision: Timmy tells his dad he has to choose between him and the coins.
- Genre Roulette: The movie is a mishmash of slapstick comedy, crime caper, romance and sentimentalist drama.
- Hidden in Plain Sight: The stolen coins are hidden in a gym bag in a department store.
- Hollywood Law: Ray is a robbery suspect, but apparently the cops can only arrest him if he opens a locker that may contain the stolen coins.
- Karma Houdini: Ray and his pals get away with the robbery, but don't manage to keep the stolen coins either.
- Missing Mom: Timmy's mother died when he was young.
- Police Are Useless: Mostly averted, as the cops quickly identify Ray and his friends as the chief suspects. Although in the final scene, they come up with a bizarre explanation as to why they cannot charge them with theft. See Hollywood Law.
- Sharp-Dressed Man: Carl, in contrast to Bobby, who is a slob.
- Shout-Out: One of the detectives sarcastically suggests he needs to talk to Sharon Stone in interrogation.
- Time-Compression Montage: Their week of fun is condensed into a montage of scenes on rollercoasters and water slides.
- Wild Goose Chase: Bobby and Carl go on one whilst hunting for the coins using a Treasure Map drawn by Timmy.