Many adventure game heroes are borderline sociopaths and kleptomaniacs. Randal is just a little more honest about it than most. He's a user. He's a layabout. He's the bad friend who gets you into trouble, then simply shrugs or goes "Whatever..." depending entirely on his mood. Were you to drunkenly give him the engagement ring you were planning to give to your would-be fiancee, he'd pawn it for rent money. After all, if you don't remember, it's OK.
In this case though, there's a problem—a curse has trapped him in a Groundhog Day loop, played out in classic point and click style. That's pretty bad. It gets worse in a hurry. Everything Randal breaks or otherwise changes also gets unstuck in time, with the universe thrashing around each time to fit in the changes—every day getting more complicated (if not always as a result of much obvious logic). The one constant is that things only ever get more complicated, up to and including his best friend repeatedly committing suicide in hideous ways that would be hilarious if they… nope, they’re just plain funny.
Dark as the humour is, though nowhere near as much as, say, Hector: Badge of Carnage, Randal's Monday pulls it off. The dialogue, while overwritten, is sharp, especially when playing around with fourth-wall moments like Randal firing the player, and his growing boredom with dealing with the cast, like the gruff cop convinced he's a murderer. In particular, Randal usually manages to avoid the trap that—without wanting to cast aspersions on specific games here—I think of as the 'Simon The Sorcerer 3D’ mistake. If a protagonist is too nasty, at least to people who don't deserve it, they become intolerable. Randal hits the right level; he's always an ass, but rarely too much a dick.
Even before his messing around does things like unleash a plague of koalas though, his world is a weird one. Just about everything on every screen is a pop-culture or gaming reference. He lives on Threepwood Street. A psychiatrist has screenshots from The 7th Guest, Maniac Mansion, and Ghouls and Ghosts on his wall. The courier company he works for just straight up uses both a Portal logo and the Planet Express shield from Futurama. Almost never are they actually connected to anything, or there as an actual joke, right down to having Harold from Day of the Tentacle do a cameo, but then calling him Robert and giving him a different personality. At times it's like playing a comedy version of Limbo of the Lost.
Pop-culture referencing is common of course—Scott Pilgrim and Spaced spring to mind. The difference is that when they did it, it was with a purpose; as part of their characters' worldview and to reflect what's going on rather than simply to be seen. On PC, games like Space Quest have thrown stuff in, but even then usually in a subverted context, like Obi-Wan and Vader's fight simply stuffed in the background, or the Enterprise visiting a drive-through.
Here, most of them don't even get hotspots. It's just "Yep, you recognised Sophia Hapgood's amulet on that shelf, have an imaginary cookie”, and far more jarring than cute. What makes it especially strange is that when Randal does actively riff instead of just show, it's usually worth a smile. Like a Gandalf stop sign declaring "You shall not pass!” or a gold Tim Schafer.
Randal's Monday has puzzles that professors at the Institute of Moon Logic would point to and ask "What the hell?"
Still, whatever. It's all harmless fan-service. And when you have a funny adventure game with a decent script, a clever gimmick, solid voices and good art, what could possibly go wrong?
Oh, right. Puzzles. And this unfortunately is where it all crashes down. At best, Randal's Monday has puzzles that professors at the Institute of Moon Logic would point to and ask "What the hell?" They're nonsensical, poorly explained, reliant on the most painful 'try everything on everything' guesswork, and feel longer than being strapped to a board until Stephen Hawking's voice synthesiser has read out the entire works of Dostoyevsky. An early one, for instance, involves combining a support pin from a globe with a nut from a broken radio to create a key which winds a clock to make a crook think he has to be somewhere else. This isn't close to the worst, just the only one there's space to even quickly describe here. Later puzzles are whole coiled up snot-strings of this nonsense.
It's a common misconception that in a comedy game, anything goes. No. Look at Day of the Tentacle and you'll see how the logic and goals have to be clear, even if the solution is from Toon Town. Randal's Monday gets it painfully wrong, mistaking convoluted and crazy for funny and logical to the point of being tedious and infuriating to play even with an in-game walkthrough for when you've had enough. Just reading some of the solutions is tiring.
An adventure can survive dropping the ball in many ways, even get away with skimping on puzzles, but when they're bad, the whole experience suffers like a hamster in a microwave. Or the person who thought that was a good idea, when Weird Ed Edison sees what they did.