If this was a 5 minute sketch..

Rating: 3/10 (31 May 2020)

..I probably wouldn't mind it's existence. But this is a paper-thin premise combined with cardboard cutout Characters and such a lack of any development that it's genuinely difficult to care about anything that's happening. Will Ferrell is fairly funny at times, at least he can express emotions. His partner in crime, Chris Kattan, however is clearly struggling to convey that he's an actual human being.
I wanted a comedy film telling a story about people, not a bunch of cartoonish caricatures in an inconsequential sequence of events.
This movie actually manages to be pretty annoying by constantly repackaging their dumb, uncreative jokes within the same movie over and over again.
Being repetitive or dumb really isn't the problem though." Dude, Where is my Car" is a dumb, repetitive movie. But it's also self-aware and creative. There is some actual craft involved and it works. A big part of that is that those guys had an actual goal. It's right there in the title.. Where is my Car, Dude? We have to find it to keep our girlfriends.
This tiny little bit of conflict and motivation makes all the difference.
A Night at the Roxbury is just a 30 second SNL-sketch stretched to 80 minutes.
This is best illustrated by the best character in this trash heap: The old Club-Owner who has one joke about someone grabbing his ass, which he repeats about 12 times. Things constantly devolve from kinda funny to "Can we move on, please?"
But hay, there is almost 10 minutes of entertaining footage to be found in this pile of needles. So don't take my word for it. And if you find yourself desperate for more Will Farrell you might actually get a kick out of this.
This could have possibly been worthwhile if they also had Jim Carrey.
But. They. Didn't.