For me, probably the funniest moment was when Willie was jailed and started confessing to all kinds of stuff.
Also, when I talked to the TRON 3000 machines.
And drinking from the fountain.
And when Ransome said “I need to find my goddamn makeup”, and then I moved the mouse over an object, and it was labeled “goddamn makeup”.
These 4 times, I laughed out loud.
One of the most funniest moments, was when I found the chainsaw in the bushes, and the can of gas at the Mansion.
When I combined those two objects, that moment was both satisfying and hilarious!
Well, it was still an obscure reference. I’m not sure many people in modern American society know the “o-rings” thing anymore. I know my wife didn’t get it when I reacted like the characters “OMG!!! LOL!”
I was a bit confused when there was a 1987 “ComicCon” Riker… everyone hated TNG until 88/89. Then this character being named “sexy Riker”… he was “babyface Riker” back then, if i remember correctly. Then, after talking to him, he looks like going back to playing with his Spaceships in bottles - I focused on the next task. Then the background soundtrack went “PEW PEW!”… I don’t know why, but that did it for me 
(and there where more, but most are already mentioned)
One of my favourite moments was he fourth law of Robotics:
"party like in 99"
“it is not a Law”
“it should be.”
Jonathan Frakes didn´t have a beard until season 2, which didn´t air before 1988.
His voice sounds a lot like comic book guy from the simpsons though, so maybe he in fact just has a beard and didn´t want to shave for the costume.
@milanfahrnholz thx - didn’t look at it through the Simpsons glasses yet. Suddenly it’s all nucularly clear!
I’m pretty sure that Sexy Riker is inspired by the character Toby Radloff in “American Splendor”.
Their voice is almost identical:
Well that movie is also about people associated with Comics.
But comic book guy somehow feels more likely to me
Honestly, despite adoring this game there was no real “laugh out loud” moment for me. Plenty of smiles and appreciation in the general sense, however. There are definitely funnier point-and-click adventures out there.
Generally, I just enjoyed the whole experience and appreciated the richness of the game. I thought it was quite funny how Reyes bought into the jokes of others, explaining why they are so funny and whatnot.
I was just replaying part of the game as Ransome and I have listened to a dialogue between him and Leonard that I didn’t experience previously. I laughed really really hard on this one.
If you don’t have already witnessed this dialog, talk to Leonard and select the following line:
“How does it feel to know that this is your peak?”
Enjoy the rest and expect a very crass joke.
(I will not post the rest here, it needs to be seen)
I had several LOL moments. There was something at the very beginning regarding the entrance to the sewers that made me laugh, but for the life of me I can’t remember what it was.
I also laughed when Reyes says “I have no idea what you just said” to Doug, partly because I liked how the voice actor said it, and partly because it really WAS this very strange sentence from Doug that I totally could not decipher. 
And then when I was completely stuck with the puddle puzzle and I was going around trying everything possible, I had Ray show her badge to someone. Nothing happened and Ray says, “Well, that accomplished a fat load of nothing.” That made me crack up so much especially because I was stuck in the game.
When Ray gave the game award to Ron. nerd
I loved to hear the familiar voices of David, Gary and Ron and Ray’s commenting and played this scene over and over again.
Also, the Sheriff made me laugh quite some time: blah-a-reno, blah-a-reno
Someone was playing the violin.
Oh yeah! That was funny! 
No. It wasn’t me. 
Oh yeah! That was it! 
Things I lol’d at: Willy asking for gluten-free donuts; The good cop bad cop shtick; Ransome being friendly with the guy at the diner. Chuck’s lines while you beat the lasers.
Yeah, beside Ransom that’s the second strong Simpsons influence I got from TWP.