Yes, I know, it's not THAT old of a movie, it only dates to 1995. However, so much has happened in our world since then, it just *seems* like it's been around for years.
I think the movie is very good and very funny, and certainly much better than critics gave it credit for (every time I see it in the TV listings it has only one star by it. Why?!). I watch it routinely (it's on TV a lot, especially USA network). Two things I like about it are the pacing, and the deeper story that plays in the background.
First, the pacing: this movie hits the deck running and never stops moving, it just keeps rolling right along, from one nutty event to the next, but it is all carefully intertwined and everything works in symmetry to bring the viewer to the (admittedly schmaltzy) happy ending. Anyway, I like it when a movie maintains a good pace or a rhythm, never letting itself get too bogged down. "Tommy Boy" is one of those.
Second, the deeper story in the background: all the times I've watched this movie, I've never lost sight of the fact that the story didn't just revolve around some big dumb guy who couldn't seem to find his way out of a wet paper bag. No, there was always in the background the sad issue of Tommy Boy's beloved father dying. Plus, another sobering issue, that of how all this will lead to rather dire economic consequences for a business (Callahan Autoparts) that's been around for a long time and has employed lots of people in the town of Sandusky. Those two grim facts of life - death in the family and impending economic consequences - make this movie more compelling watching than one may realize, and I think this movie will hold up well over the years to come just for those reasons.
But enough with the gloom already. This movie is just plain FUNNY, thanks not just to Chris Farley, but to an entire cast that seems to work really well together. I couldn't envision the cast members being changed or replaced in any form. And Chris Farley did such a seamless depiction of this funny guy named Tommy Boy, that I still, in my heart of hearts, just know that there really IS a big dumb funny guy named Tommy Callahan, somewhere in Sandusky, Ohio, who is running an autoparts factory. No, there really IS a Tommy Callahan, believe me... It's kinda' like Pee-Wee Herman: that wasn't really an actor named Paul Reubens playing him, no! - there really IS a Pee-Wee Herman, who is totally in love with his bicycle, and has a dog named Speck...
Funny, but I look at waitresses in restaurants just a little differently now (thanks to that wonderful scene where Tommy Boy explains to Helen why he sucks as a salesman). And any time I'm feeling down, I just remember: "Fat guy in a little coat." "Hey, Prehistoric Forest!" "Holy Schnikees!" "Hey, quit playin' with yer dinghy!" plus many other lines, LOL LOL Those will always cheers me up!