I wanted to do a list of comedy games, but I think people rarely think "I want to play a comedy game"; to me, the phrase brings up some kind of jokey, goofy game, like many of the poorly made Twine games that people make now.
Instead, the funny games I enjoy tend to have an actual, deep story with hints of sadness, danger, or drama, and the comedy is a welcome relief from that. More of a dry or British humor. So that's what's found in this list. Absurd games are in their own list.
Also, many games like Curses! or Adventure are quite funny in parts, but it's not an overriding theme. Similarly, I love Six by Clarke, but find it charming and adventurous more than funny.
As always, feel free to add games in the comments.
1. To Hell in a Hamper by J. J. Guest (2003) Average member rating: (112 ratings)
MathBrush says:
You are in a balloon approaching a volcano, and must convince your hoarder companion to lighten the load. Short-to-mid length
2. Child's Play by Stephen Granade (2006) Average member rating: (54 ratings)
MathBrush says:
The first game that ever made me laugh. You are a baby trying to get your favorite toy and avoid a rival. The background includes a group of moms with one out-of-place dad.
I literally laughed out loud several times in this game. You are a test subject working for an evil reptilian female doctor, exploring the galaxy for salvage.
A bit of darker humor by the same author. A parody of youth detective novels, also in Twine.
8. Lost Pig by Admiral Jota (2007) Average member rating: (499 ratings)
MathBrush says:
This game and the next are highly acclaimed (in top 10 interactive fiction of all time by many measures), but I didn't like them quite as much as the others. In this game, you play a not-quite-smart orc hunting a lost pig.
9. Violet by Jeremy Freese (2008) Average member rating: (392 ratings)
MathBrush says:
Another very popular game, this one grated on my nerves because it reminded me of work. You are trying to finish your dissertation (or at least get far on it) while the narrator, your girlfriend, tries to keep you from procrastinating. I was glad not to have this nagging in real life, so I didn't identify with the game, but most people love it.
10. Hunger Daemon by Sean M. Shore (2014) Average member rating: (66 ratings)
MathBrush says:
Smoothly polished Lovecraftian parody. Won IFComp in 2014; short-to-mid length, and very fun.
11. Dinner Bell by Jenni Polodna (2012) Average member rating: (54 ratings)
MathBrush says:
Dogs are doing psychological tests on you. Find food, but don't eat it!
Gain superpowers from animals in the jungle. The first Quest game I have played. Good author.
13. Enlightenment by Taro Ogawa (1998) Average member rating: (41 ratings)
MathBrush says:
Great dry humor, and very hard. You almost beat a Infocom-type game, but now you must LOSE all of your light sources, and the troll in front of you is not helping.
One of the most highly-rated Speed IF ever. A sassy fish game.
15. Conan Kill Everything, by Ian Haberkorn (2005) Average member rating: (67 ratings) MathBrush says:
A one-room game where Conan kills everything. Less polished than the other games on the list, but still generally entertaining.
16. Being Andrew Plotkin by J. Robinson Wheeler (2000) Average member rating: (55 ratings)
MathBrush says:
You enter the brain of one of IF's premier authors. A parody of Being John Malkovic. Even if you don't know much about Zarf/Plotkin, the romance and robots are very amusing.
17. Wishbringer by Brian Moriarty (1985) Average member rating: (110 ratings)
MathBrush says:
One of Infocom's very best games, by the author of Trinity and the Lucasarts game Loom. Includes a platypus kingdom and dangerous, sentient boots.
18. Hollywood Hijinx by Dave Anderson, Liz Cyr-Jones (1986) Average member rating: (34 ratings)
MathBrush says:
Another Infocom game. The mechanical mutant chihuahua did it for me.
19. Taco Fiction by Ryan Veeder (2011) Average member rating: (119 ratings)
MathBrush says:
Winner of IFComp a few years ago. To me, the funniest parts were going off script and seeing what happened. More of a drama game, but it worked as comedy for me, as well.
A very funny game that is now freely available (everyone should get it!) Second-best-selling Infocom game ever. Very hard, though; I just used a walkthrough to get to the best parts.
21. Oppositely Opal by Buster Hudson (2015) Average member rating: (70 ratings)
MathBrush says:
A game with a valley-girl witch. The language threw me off at first, but the puzzles are actually quite funny.
22. Lock & Key by Adam Cadre (2002) Average member rating: (75 ratings)
MathBrush says:
Create a dungeon, watch an adventurer escape. Buying the items and watching the adventurer are great.
23. Planetfall by Steve Meretzky (1983) Average member rating: (122 ratings)
MathBrush says:
Floyd the robot is a very amusing sidekick. Some other funny moments in this Infocom game, available on iPad.
24. Secret Agent Cinder by Emily Ryan (2015) Average member rating: (27 ratings)
MathBrush says:
Tongue-in-cheek interactive webcomic about Cinderella as a French revolutionary operative.
25. Birdland by Brendan Patrick Hennessy (2015) Average member rating: (161 ratings)
MathBrush says:
Great Twine game about a summer camper dreaming of bizarre, anthropomorphic birds.
26. The Cabal, by Stephen Bond (2004) Average member rating: (28 ratings) MathBrush says:
An old-school enthusiast comes to grips with the influence of a dark and shadowy Cabal of prominent IF writers.
27. A Fine Day for Reaping by James Webb (aka revgiblet) (2007) Average member rating: (26 ratings)
MathBrush says:
A nonlinear parser game. You are death, and you've been given five targets to help move along. There are multiple solutions to all 5 things, and a Terry Pratchett/Monty Python vibe.
28. In a Manor of Speaking, by Hulk Handsome (2012) Average member rating: (26 ratings) MathBrush says:
A short-to-mid length surreal game based on puns. Walk in a vast dessert, pick up some (fuzzy and yellow) chicks, and try to get home.
A game that pretends to be the 4th game in a series. You are Dutch Dapper, interstellar hero, asleep in your bed, when a mysterious knock comes at the door.