The Appointments of Dennis Jennings (1988)

Starring: Steven Wright, Rowan Atkinson, and Laurie Metcalf, with small roles from Mike Starr and David Hyde Pierce
Grade: A-

The enigmatic Steven Wright hits us with an Oscar-winning short film just as intricately goofy as his own comedy.

Summary

In the opening credits, we see Dennis Jennings (Wright) hunting and shooting at psychiatrist Dr. Schooner (Atkinson).

Three months earlier, Dennis goes to the office of Dr. Schooner to meet for a therapy session. After an awkward exchange with the doorman (Starr), he’s told where to go in the building. In their session, Dennis talks about how he wants to meet his stepfather, despite his great relationship with his real parents, and how he’s worried no one presents themselves to him in the way they truly are. As he says this, Dr. Schooner, with no interest in Dennis’s random rants, writes up his grocery list. Following this, Schooner cuts the meeting short, and Dennis goes back to his oddball apartment. Sometime later, Dennis goes to work at his waiter job. There, his girlfriend Emma (Metcalf) eats at the restaurant with one of her friends, mentioning to her that Dennis sleeps with a parachute on but doesn’t like to talk about it. As Emma tells her not to tell anyone except a few friends because Dennis has a paranoid feeling people talk about him behind his back, Dennis approaches the two to greet them. Right away, Emma asks if he’s completed basic tasks for the day like locking his door and turning off the stove. Once Dennis realizes he forgot to feed his fish, he rushes home and does so immediately. Back at another session at Schooner’s office, where Schooner seems just as careless as before, Dennis goes through another series of random rants. He asks Schooner if he thinks he’s crazy. Schooner hesitates but says “No”, even though we know how he really feels. Then, Dennis talks about how beautiful Emma is but admits he doesn’t trust her.

Unfortunately, Dennis will find out he is right to not trust her, and it leads to him finally losing it on Schooner.

My Thoughts:

Being that this is my first review of a short film for this site, I wanted to make it a good one. After admittedly minimal research, I landed on The Appointments of Dennis Jennings. Was it just because Steven Wright had his creative genius all over it?

Yes, that is 100% the reason.

A lot goes on in this brisk half hour as we get a glimpse of the mind of Dennis Jennings, an anxiety-riddled, middle-aged man whose quirks seem to be tearing up his psyche. Accompanied by Rowan Atkinson as his uncaring psychiatrist and a decent cast for such a film, we get an interesting story and layered comedy that will take a second viewing to really appreciate the humor Wright brings to the table in his writing. It’s a lot like his stand-up. You laugh at first because it’s funny at the surface, but when you play the joke over in your head, you start to realize how well-thought-out it is and laugh a second time. The bit where he’s listening to his voicemail on a tape recorder was legitimately hysterical, as well as the cutaway gags like him not trusting anyone behind him when he’s driving. Then again, this is just the tip of the iceberg with this nuanced short film. I don’t want to spoil the rest of it.

In comedy, it takes a serious genius to make the simplest of gags come off as funny as they do here, but this is why Stephen Wright is looked back on as one of the funniest men of his era.

The Appointment of Dennis Jennings is a great example of the backwards humor, nonsensical happenings, and one-liners that made Wright a legend in comedy. Not everything works and it gets a little darker than one would expect (which arguably benefits the narrative), but it’s interesting enough that everything balances out. For a short film, this one is a surprising amount of fun.