1998's A Night at the Roxbury Was Always Awful and Brutally Unfunny But Now It's Creepy As Well

Where to start with this one?

One thing that I do not miss about my old life as the head writer for The A.V. Club was the stomach-churning anxiety I used to experience just before doing an interview. This was particularly pronounced if the interview was in person. 

And, on the very rare instance that I found myself doing an in-person interview with someone who was promoting a movie or book or album that I deeply loathed it could be excruciatingly awkward. 

That was the case when I interviewed Amy Heckerling and Chris Kattan when they were in Chicago promoting A Night at the Roxbury in 1998, when I was twenty-two years old and a relative newcomer to pop culture writing.  

I don’t remember, but I suspect that we asked to interview Heckerling alone because she’s the person we really wanted to talk to, but they said it was a package deal. 

I had no way of knowing just what a strange proposition that would prove to be. In his memoir, which I really should read and write about at some point, Kattan writes that Lorne Michaels pushed him into having a sexual relationship with Heckerling, the red-hot director of Fast Times at Ridgemont High and 1995’s Clueless so that she’d direct A Night at the Roxbury. 

Kattan and Heckerling apparently had sex on a couch in her office but she ended up only producing A Night at the Roxbury. Incidentally the two movies I was thinking about writing up today were Stuart Saves His Family and A Night at the Roxbury, both of which were co-written by men who had secret sexual relationships with Heckerling. Harold Ramis, the co-writer and director of Stuart Saves His Family even had a secret child from his secret affair with Heckerling. 

That is a strange coincidence. 

Will Ferrell’s friendship with Kattan apparently ended over his relationship with Heckerling. That helps explain why the duo promoting A Night at the Roxbury was not its two stars but rather a star and a producer. 

It also helps explain why the atmosphere was awkward and tense even before Kattan or Heckerling nervously asked me if I liked the movie. 

If I were honest, I would have responded, “God no! It’s terrible! It’s a movie based on a sketch where two guys bobbed their heads in time to music. How could it NOT be godawful? Jesus, you know that you’ve made just a worthless, worthless, brutally unfunny piece of shit. Why would you even ask me I question like that? Let me ask YOU a question. Do YOU like the movie? Are you proud of it? Is this what you envisioned when you were given seventeen million dollars to make a major motion picture?” 

I am not brutally honest, however. I hate conflict so I said something along the lines of “Sure, there were things about it I liked” then singled out the two least terrible elements of the movie, one of which was a super-timely Say Anything homage and the other of which was Richard Grieco’s cameo. 

If I remember correctly, after the part where I profess to have enjoyed at least some of A Night at the Roxbury there is an editor’s note to the effect of “He’s lying.” 

Good times! Good times! It was so awkward yet it would have been MUCH worse if I’d known Kattan and Heckerling’s history. 

I vaguely remember asking why they changed the setting of the action from New York to Los Angeles and Heckerling said something to the effect that if it was set in New York they’d have to deal with the whole Bridge and Tunnel thing, where people from less exciting, important boroughs venture to Manhattan to seek their fortune and pursue their dreams, so it was easier to just set it in LA. 

The only upside to making A Night at the Roxbury in Los Angeles is that Clueless is a quintessential Los Angeles movie and if Michaels couldn’t get Heckerling in the director’s chair he could at least have director John Fortenberry, a sketch comedy veteran whose feature film directorial experience was limited to the notoriously terrible Pauly Shore vehicle Jury Duty, make a movie with a Clueless vibe. 

Fortenberry even directed four episodes of the Clueless television show. This ends up working against the film because it’s similar enough to Clueless to suffer by comparison. 

It’s just like Clueless only, you know, terrible. So instead of Cher Horowitz living a life of leisure and privilege alongside a loving, supportive dad played by Dan Hedaya we instead have a pair of doofuses living lives of leisure and privilege alongside a perpetually annoyed dad played by Dan Hedaya. 

One of the many, many problems with making a movie about the Roxbury Guys is that, in the sketches that inspired the movie the nightlife lovers are assholes. They’re clearly drunk and high on cocaine when they go to nightclubs to sexually harass attractive women. That explains why they’re always rubbing their noses: to make sure that they don’t let even a tiny glob of booger sugar go to waste. 

What’s to like about that? So A Night at the Roxbury makes them more sympathetic by having them act like they’re drunk and high on cocaine without ever showing them use any illicit substances other than whippets. 

Here they’re not creeps perpetually trying to get laid by shamelessly hitting on attractive women in an aggressive bordering on hostile way: they’re awkward doofuses and possible virgins who have no idea how to speak to women, let alone seduce them. 

In the sketches the characters behave identically. They dress the same.They dance the same. They have the same attitude towards women. 

In A Night at the Roxbury, however, they are pretty much the same but also somewhat different. Doug Butabi (Chris Kattan) is the brains of the operation, an idea man whose one idea involves opening a club where the outside is the inside and the inside is the outside. 

Doug works a thankless job at his dad’s fake flower store but dammit, he has dreams. It’s okay to work a retail job in movies like this if you constantly talk about your dreams of wanting more but not if you are content with your lot in life. 

If Doug is dumb then his brother Steve (Will Ferrell), who also works at his dad’s store, is dumber. He’s a towering goofball with a brain full of pudding and gummy worms whose life revolves around going to legendary real-life club Roxbury and being denied entrance. 

The film’s premise is lazily ripped off from Saturday Night Fever. Its protagonists are wage slaves by day who live for the nighttime and the nightlife. But where John Travolta’s Tony Manero was a racist, sexist creep hopped up on pills and booze the Butabi brothers are ostensible innocents who dream of someday knowing a woman’s sensual touch but apparently have zero sexual experience. 

What they do have are dreams. Or at least one of them has a dream. Doug stumbles closer to achieving his stupid, stupid dream when the brothers get into a minor traffic accident with Richard Grieco (THE Richard Grieco), who gets them into the Roxbury, where they meet a powerful club owner played by Chazz Palminteri who inexplicably takes a liking to them and agrees to take a meeting with them. 

Seeing the brothers with the wealthy club owner leads shameless gold diggers Vivica (Gigi Rice) and Cambi (Elisa Donovan), to think that the Butabis are wealthy and powerful. 

So they have sex with them with the implicit understanding that doing so will help them financially or in some other way. When they discover that the man-children live with their parents and have no money or power of their own they are mortified. 

This isn’t remotely funny but it is casually misogynistic. That’s also true of a subplot involving Emily Sanderson (Molly Shannon), who works at the lamp store next-door. 

Emily shamelessly throws herself at the oblivious Steve, who insists that a relationship between them would never work out, as he’s a rebel and she’s a virginal girl next door. 

Emily replies that she’s a college student, and college is basically a drunken orgy with Cliff’s Notes, which is as close as the film gets to a funny line of dialogue.

The easily led dumbass is convinced to marry Emily for the sake of his family and his business. The brothers have a fight on account of the third act needs conflict, which the film otherwise desperately lacks. 

We end with the aforementioned Say Anything homage, which finds Doug interrupting a marriage of convenience to a harridan he doesn’t even like, let alone love, with a boombox playing Haddaway’s “What is Love.”

Steve is instantly reminded of what really matters in life: going to clubs with his brother while definitely not high on cocaine and bobbing his head in unison to Haddaway’s deathless club smash. 

We end with the boys meeting some nice girls in the form of a woman who works at a credit card company Doug calls regularly played by Meredith Scott Lynn and a police officer played by Jennifer Coolidge. We know they’re nice girls because they’re dressed modestly and express no interest in sex. 

At this point A Night at the Roxbury is a very old movie. It has been a quarter century since it came out. Watching it I was struck by how young Ferrell looks in it. He was just a baby at this stage in his career, a talented sketch performer and physical comedian who hadn’t quite figured out who he wanted to be as a movie star beyond a Saturday Night Life cast-member making the movies the boss told him to make. 

A Night at the Roxbury was alway sad and desperately unfunny but the revelations about its making render it something else as well: creepy. It’s now full of bad vibes and weird energy, which makes it even sadder and more ridiculous that Kattan wants to make a follow up and claims that people constantly ask him when the sequel will be coming out. 

To paraphrase Clint Eastwood’s catchphrase from In the Line of Fire, that’s not going to happen but it is poignant that Kattan apparently thinks it’s at least a distant possibility and that Ferrell would be onboard at this stage of his career. He’s definitely not at the apex of his popularity but he’s not doing that badly either. 

I’m going to go out on a limb and say that Ferrell would probably be more open to doing a sequel to Barbie, the most successful film of the year than A Night at the Roxbury, which was the sixty-first top grossing film of 1998 for reasons that should be obvious. 

Ferrell and Kattan should just be grateful that It’s Pat exists, thereby sparing A Night at the Roxbury the shame of being the worst Saturday Night Live movie. 

Up next: Stuart Saves His Family, finally!