Getting Even with Dad (1994)

Synopsis
A criminal trying to reform is forced to endure the most humiliating punishment of all -- hanging out with his son -- in this family comedy. Ray Gleason (Ted Danson) is a thief whose ambitions far outstrip both his skill and his intelligence; Ray is just bright enough to have realized this, and he's decided to go straight and open a bake shop (he learned how to decorate cakes during his last stay in prison). However, Ray needs to raise some working capital, so in association with his buddies Bobby (Saul Rubinek) and Carl (Gailard Sartain) he is planning his last heist, in which they hope to walk away with a highly valuable collection of rare coins. Ray also happens to have an 11-year-old son, Timmy (Macaulay Culkin), whose mother died several years ago; Timmy has been living with his aunt, but when she gets married and goes away on her honeymoon, Timmy ends up staying with Ray. Timmy is a lot smarter than his dad and quickly figures out what Ray and his cronies have been up to; he's long felt a great deal of resentment toward his father for not being around when he needed him, so Timmy steals the loot from the robbery and uses it to blackmail Ray into spending some quality time with him. Timmy also thinks that it's high time Ray settled down, so when he notices that Theresa (Glenne Headly), an undercover cop, has been following Ray's trail, Timmy tries to play matchmaker and bring them together. Getting Even with Dad would prove to be the next-to-last screen appearance for former pre-teen superstar Macaulay Culkin; he was 14 when this film was released, and within five years he was a married man attending the Rhode Island School of Design. ~ Mark Deming, All Movie Guide