I had a stark realization: Tommy Boy was released in 1995, which means it’s old enough to legally drink. How fitting. Fun story: I watched this film when it first came out with my best friend Lisa. We went to the theatre and proceeded to laugh our early-teenager asses off, without parents, for an hour and a half. To this day, she will still look at me with innocent eyes and ask, “What’d ya DO?” Good times, my friends. Now under most circumstances, I’d shade the hell out of movies like this: cheap fat guy humor, shoddy plot, etc. I can’t though. I love it too much. Let me count the ways.

Don’t be hatin’.

On a door, gutterminds. Ever see that Far Side cartoon of the School for the Gifted, where the genius is pushing on a door that states “PULL”? Within two minutes, this movie goes for that gag. And it gets me every damn time.

Another true story: I once worked with someone that had no fucking idea that Herbie Hancock was a real person. Imagine my horror at having to explain not only who Herbie Hancock was, but what he was famous for. It was painful. So every time that someone mentions Herbie Hancock, I giggle and die a little on the inside.

Tommy (Chris Farley): “You know, a lot of people go to college for seven years.”
Richard (David Spade): “Yeah. They’re called doctors.”

Good Christ do I love the introduction to Lowe’s Paul. The punch to the window on the bus for the kid making the face… yeah, I will cop to wanting to do that. You have to admit, some kids are serious assholes and the temptation is real. Considering that the character is a complete ass that winds up getting pummeled throughout the film, it’s fitting.

David Spade is such a smart ass in this film. God do I love his one-liners. Between the quip about neckties to enthusiastically exclaiming, “Prehistoric Forest!” after whacking Tommy in the face with a board, Spade’s Richard is relentless. It’s a bit like watching me in my daily life, so there’s a kinship there. And make no mistake, Farley’s Tommy gives as good as he gets. For the record, my favorite comeback is, “Who was your favorite Little Rascal? Alfalfa, or is it Spanky? Sinner.” I love nothing more than to call people “sinner” in Chris Farley’s cutesy voice.

Shut up, Richard.

Julie Warner’s Michelle has quite a bit going for her: she’s got a fun voice, she looks approachable, she’s got the knowhow to make a warehouse run, and her rant to the teasing kids is epic. Proving once again that it takes a woman to lay a serious smackdown.

Between the bad sales meetings and the deer in the backseat of the car, it’s memorable. For anyone that’s ever been involved in a bad road trip – let alone a business trip from hell – this hits a little close to home. I’ve been on this trip in both business and vacation form. You laugh in part because otherwise, you’d cry. Hard.

My father loves The Carpenters, and as such, I was tortured with their Christmas album every year. The song in this film is one of the few Carpenters songs I can tolerate, and it’s due to this film. It’s the crying whilst singing that gets me every time. The crowning moment is the flip of the hood as they’re barreling down the highway. Really, come to think of it, it’s all the singing in the car. If you ever have the grave misfortune of being stuck in the car with me for a long time, you will find a ton of singing going on. It’s terrifying and great at the same time.

“I loooooooove youuuuuuu….”

First it’s the door. Then it’s the windows. Then there’s a baby gate where the driver’s side door should be. Then tarp covering the car where the hood should be. And you know what? You haven’t lived until you’ve ridden in a car like that. I had a car once, as a teenager, nicknamed The Death Mobile that had a cherry red hood on a gold car with bungee cord holding it down, and you could hear gas sloshing around in the back. The best part? The speedometer didn’t light up at night, but you knew when you had hit the 45 mph mark because the hood would try to lift up. You don’t value life and how a car looks until you’ve driven and/or ridden in that. A true walk down memory lane.

Having flown recently, I would have killed to have had flight attendants like Tommy and Richard. In fact, I love Richard’s speech so much that I think we should change all safety precautions to that. He’s right: if you can’t work a seatbelt, you shouldn’t be flying. And the crack about crashing into a mountain? Genius.