I actually remember Tommy Boy getting released back in the 1990’s, as well as how little I ever wanted to see it.

I am really not sure why that was. I was a Saturday Night Live fan of the era, and I usually enjoyed the early 90’s cast as “my” era of the show. I wasn’t always a fan of Chris Farley, but I dug other SNL produced movies like Wayne’s World.

For whatever reason, I got it in my head that Tommy Boy looked “dumb”, and that was that for thirty years for me. It’s a mistake I made before and regretted; I remember thinking the same thing about Groundhog Day, and when I finally watched that within the last five years, it only turned out to be one of the greatest comedies ever made.

So this week when I decided to give the cult classic a go, I went in trepidatiously but curiously…

Tommy Boy tells the tale of Tommy Callahan, the son of Big Tom Callahan who owns Callahan Auto. After seven grueling years away at college, Tommy graduates with a D+ and is finally in line to help out in the family business. And this all comes right as Big Tom is about to marry his new paramour, Beverly.

At Tom and Beverly’s wedding, Tom collapses and dies of a heart attack, leaving the stock in Callahan Auto split between Tommy and Beverly… and the company in a lot of financial trouble. So Tommy sets off with Tom’s assistant Richard on a trek across the country to sell Callahan Auto’s new brakes to any and all dealerships that will take them.

While the two would-be saviors of the company do their best, Beverly and her son Paul are left back home, and they have their own machinations for Callahan Auto…

TWO UPS AND TWO DOWNS

+ David Spade’s quick sarcastic wit and facial expressions are the star here. He really makes this picture work. It’s weird to think how he just kind of vanished from Hollywood aside from the occasional Adam Sandler given role. He was a talented guy in comedy roles. And hell, he was Cuzco, the star of probably my favorite Disney movie! What more can you want from a guy?

I know this is Farley’s picture first and foremost–we’ll get to him in a second–and that Spade is the clear number two guy. But Tommy Boy doesn’t work with almost anyone else playing Richard. He makes the movie go. His chemistry with Farley is impeccable, and his ability to hit a delivery dead-on makes most of the flick’s best moments.

+ Tommy actually has more of a character than I would have thought. He has some real growth and actually comes across as a[n almost] fully realized human being. Especially early on, he plays Tommy as a complete neanderthal who is absolutely worthless on his own. But as Tommy Boy goes on, Farley shows moments of true emotion that evoke sympathy from the audience.

It’s a credit to Farley that he was able to make Tommy ultimately such a multi-faceted character, and it really makes you wonder where Chris would be today if he had not passed away so tragically young. Would he be another Sandler guy who only shows up in Grown Ups sequels? Or would he have moved on to being a guy that could be relied upon to do more dramatic stuff?

Regardless, one of my most pleasant surprises watching this for the first time was Farley showing unexpected competence as an actor in his portrayal of Tommy.

– Boy, a lot of the jokes in this one are “Tommy is fat” or Tommy hitting his head on things. They get old incredibly fast. To be fair, the stuff in Tommy Boy that is funny is REALLY funny, but I would say 70% of the jokes are repetitive or just plain miss. Which is what it is: some movies are rapid-fire jokes and are happy to have even a small percent actually land because that will still pop an audience with good frequency. And Tommy Boy is clearly going for that approach. But I think I personally prefer movies that are a little smarter in their comedy. Which makes me sound more snooty than I man; I mean, I still champion Deep Murder to anyone who will listen, so the hypocrisy is real.

So yeah, I’m the guy that didn’t think “Big guy in a tiny coat” was that uproarious. I had just gotten a little tired of fat jokes by that part of the movie.

– The Bo Derek / Rob Lowe stuff with their trying to undermine Tommy and Richard and steal the company out from underneath them feels annoyingly extraneous and like the movie just threw them in so that there was an antagonist in addition to a race against the clock. You could easily write this movie without those characters, and it probably works just as well. And then you would get to spend even more time with Tommy and Richard, and they’re the stars of the show.

I feel like sometimes movies throw in actual human antagonists because they don’t trust an audience enough to accept stakes and the circumstances of plot as the villain. If this story was just about Tommy and Richard failing at making many sales and having to race against a clock to make a deal with Ray Zalinsky, that would be just as gripping as Rob Lowe’s character fudging some computer numbers.

I do normally adore Rob Lowe. I just don’t think he had loads of added value here, essentially playing nothing more than his well-worn heel character.

OVERALL

I will confess to having had more fun with Tommy Boy than I thought I would. I was deeply worried when I started this watch that my early years’ misgivings about this film would come true. But Farley’s surprisingly effective portrayal of Tommy as a real character and Spade’s comedic timing won me over. It’s not my favorite comedy ever or anything, but it’s a shame I missed out on its heyday.