So my recent introduction to the Saints Row series has gotten me thinking about both fun gameplay and comedy in video games.

There are a lot of games that are fun, though the most fun games often aren't necessarily the "best" games, at least to me.

But there aren't a lot of games, at least that I know about, that are actually laugh out loud funny. There have been some comedy games: Planetfall, Bard's Tale (remake), Duke Nukem, Space Quest, Hitchhiker's Guide, and to some extent Borderlands and FO 1 & 2, but the ones I've played weren't all that funny. At most there are some funny moments or concepts in games, but they're more likely to get a brief smile than a laugh. (Also, most of these games are pretty old, are studios not interested in making humorous games?)

So my dual question is: what games have you played that stand out as being particularly fun? And what are the funniest games you've played, games that have evoked more than just a smile or a moment of appreciation?

Currently both my most fun and funniest award goes to Saints Row 4. I'd also give SR2 a nod for the FUZZ minigame, which had me laughing out loud. After these two, Fallout 1 & 2, for the style and ambience rather than any particular moment or situation.

All games are fun, I'd say. I think that's one of those boxes you have to check of before you publish your game.

In terms of games that are particularly funny. I got a kick out of watching all the cutscenes in the Dead Pool Game. Dead Rising 3 also had some funny moments.

South Park: The Stick of Truth (fun and hilarious).

If that is not your cup of tea then there is the Saints Row series.

Even Saints Row can be a bit distasteful too. So last I recommend On the Rain-slick: Precipice for Darkness.

Yes, but fun means different things in different contexts. I love strategy games for example, but the fun in playing Crusader Kings vs Dark Souls vs Arkham Asylum are very different experiences. I like exploring in Skyrim more than any other sandbox game, but nothing matches, IMO, moving around the city in Saints Row 4. In SR4, the movement itself is fun, though the exploration is a little meh. In Skyrim, there's some itch that's pleasant to scratch, and maybe some kind of discovery payoff.

I can't believe I forgot this one. And it's recent too.

Portal 2 had me laughing out loud.
This is mostly due to Wheatley's dialog, and being superbly voiced by Stephen Merchant.

Bully Scholarship edition and GTA San Andreas are great fun in my book (gameplay, characters, dialogue).

As for pure comedy I'm a big fan of laid back point&click adventures like Broken Sword, The Book Of Unwritten Tales, Monkey Island, Lost Horizon.

http://en.wikipedia.org/wiki/Day_of_the_Tentacle is a very funny game, and is actually getting a remake later this year.

I will second this. The Cave Johnson parts are hilarious as well.