Funny story, I definitely remember this one a lot more fondly than upon my re-watch of it, these 15 years later. It's strange, because this one has a great cast of comedic actors, and should otherwise be right up my alley because, much like 'Clerks', it's a look at the retail and restaurant workers that we so often take for granted. Being a retail guy, myself, I tend to enjoy something like this a bit more than others - especially when they really stick it to horrible customers (call it a guilty pleasure).
Taking place in a 24-hour period, this one shows an average day in the life of one particular Shenaniganz staff. Headed by Monty (Ryan Reynolds), we get our first glimpse immediately into the material that lies within this movie that simply would not fly today. Monty is a womanizer, trouble-making type, who has the hots for the new 17-year-old hostess, Natasha (Vanessa Lengies) - chomping at the bit for her to turn 18 so that he can make his moves legally. Beyond that, the older boss, Dan (David Koechner) also has his eyes on her, and it's honestly creepy enough that Ryan Reynolds is doing his thing. So, plenty of workplace harassment, even though Natasha pretty well goes with it.
Monty spends his day showing the new hire, Mitch (John Francis Daley) the ropes, and introducing him to the other staff. Among them, include the rest of the wait staff, Mitch's ex, Serena (Anna Faris), temper-throwing Naomi (Alanna Ubach), innocent Amy (Kaitlin Doubleday), insecure Calvin (Rob Benedict) and Dean (Justin Long) who is essentially the main focus of the film, while Reynolds provides the overall comedy relief, taking the reluctant Mitch under his wing. Dean's character is basically the guy who doesn't quite know what he wants to do with his life, torn between a huge opportunity at the restaurant, and getting out into the world to do his own thing.
We also have the kitchen staff, consisting of sex-hungry Raddimus (Luis Guzmán), the wise Bishop (Chi McBride), and gangsta wannabes, Nick and T-Dog (Andy Milonakis and Max Kasch, respectively). While Dean's story is going on, the rest of the crew are giving whole new meaning to the name "Shenanigans", especially when it comes to a game that involves guys showing other guys their private parts, and in turn, getting to kick them and call them something that would never, ever, ever fly these days. I won't say it, but you can probably probably put the pieces together. And while the underage issue is addressed by the end of the film, the other thing mostly turns into a punchline. So, I can absolutely see there being a strong dislike nowadays for this one. It's sorely dated, and the only leeway I can really give it, is the fact that it's a healthy R-rating on a straight-to-video movie. You kinda tend to expect some over the line stuff in that case.
Anyway, the guilty pleasure aspect on this still remains, as this staff kinda just does what we all wish we could get away with. Remember the cardinal rule to not mess with people who handle your food - perhaps the biggest takeaway from this for most people. And they are sure (at least the first time) to show you what a horrible person the customer used for this example is. But I definitely got way less out of it on this viewing. It's actually a pretty harsh and mean-spirited movie, with the main plot at its most simplistic. It's mostly reliant on dialogue and gags, a lot of it pretty low-brow. I definitely liked it better 15 years ago. Nowadays, you can see how badly its aged.