I predicted that this week I might have the first film of the challenge to drop below the halfway mark on my chart, and while I was right about that, I want to stress that I did enjoy Tommy Boy more than I actually expected to. 1990s buddy comedies have a tough row to hoe with me.
Tommy Callahan (Chris Farley) has a tough row to hoe himself – he’s the none-too-bright son of a midwestern manufacturer whose big house and new money doesn’t help him get through college in less than seven years (he graduates after gleefully passing a history test with a D+). But that doesn’t get him down; he returns home celebrating and excited to join his father’s business. Not as excited is Richard Hadyen (David Spade), an old high school classmate who works for Big Tom Callahan and is bitter that Tommy gets all the praise without having any of the smarts. When Big Tom dies, Tommy and Richard are forced to go on the road together to get enough sales to keep the business afloat.