Ranking the 10 best, and 5 worst, comedy games of all time

The appeal of Telltale Games’ Strong Bad’s Cool Game For Attractive People isn’t hard to understand, whether you meet its titular criteria or not: The five-episode adventure series is pretty much exactly what anyone hoping for a playable version of The Brothers Chaps’ beloved Homestar Runner might have been dreaming of back in 2008. With dialogue overseen (and, of course, performed) by series creators Matt and Mike Chapman, SBCGFAP is filled with Easter eggs and inside jokes for fans of the beloved Flash cartoon phenomenon. More importantly, it taps into the same cartoon-y, video game logic that made Strong Bad and his various frenemies such an online hit, tasking you with cluing into the wacky thought processes that power Homestar’s world. A great jorb, all around.

Great comedy in video games isn’t just something that happens in dialogue, or even through visual gags: It can also be expressed through the play itself—or, to put it another way, through the horrible, awful things a video game can do to you when it’s in the mood. Anyone who’s spent more than five minutes with I Wanna Be The Guy, released for free on the internet by Michael O’Reilly in 2007, will be aware that the game has a powerful sense of humor—and that it’s the kind that gleefully yanks a chair out from under you just as you’re about to sit down. So brutal, and so popular, that it spawned a whole series of masochism-based “masocore” imitators, IWBTG is a masterpiece of subverting expectations to deliver laughs, and frustration, in (at least initially) equal measure. The first time you dodge under a series of swift-moving apples—and then have one of the bastards fall up at you when you’re trying to leap over it instead—you’ll understand the nasty, brilliant comedy O’Reilly’s game traffics in.

For many years, comedy in video games was largely the domain of point-and-click adventure games, which deployed tightly crafted scripts, humorous problems, and, increasingly, high-quality voice-acting to turn themselves into an effective take on playable comedy films. Sierra Entertainment’s titles, especially, tended to veer toward the funny, whether it was the punny cheerfulness of Lori and Corey Cole’s Quest For Glory games, or the deliberately over-the-top sleaze of Al Lowe’s Leisure Suit Larry. For our money, though, the funniest of the bunch was Scott Murphy and Mark Crowe’s Space Quest series, with 1991's Space Quest IV standing out as the cream of the comedy crop. Starting with an absurd time-traveling premise—semi-heroic space janitor Roger Wilco finds himself bouncing through his own timeline, eventually ending up in Space Quest XII, Space Quest X, and even getting blown back to the original Space Quest I—and featuring a stand-out performance from Laugh In’s Gary Owens as the game’s endlessly derisive narrator, Space Quest IV is as funny as its puzzle-solving is nasty. (But hey: When the death descriptions for, say, choosing to drink a big ol’ puddle of acid are as witheringly funny as the rest of the game, who’s complaining?)

Perhaps the funniest treatise on the total meaninglessness of human choice ever crafted, Davey Wreden and William Pugh’s The Stanley Parable is also one of the first funny video games to take video games themselves as its subject. Originally created as a Half-Life 2 mod, before being transformed into its own standalone project in 2013, TSP casts you (sometimes very aggressively) as Stanley, a regular office drone who finds himself alone in his office one day. As the game’s unseen narrator (played, with impeccable smarm, by actor Kevan Brighting) takes increasingly harsh control over Stanley’s actions, the urge to rebel only builds—as does the dawning realization that “rebelling” is basically meaningless in a world entirely constructed around a designed narrative like video games. Existential despair has never been so fun!

As we noted in the intro to this ranking, video games have had humor since before they even had graphics, with early text adventures like Infocom’s Zork offering up frequently absurd writing to players, and demanding equally silly solutions in turn. A fan of the genre, Hitchhiker’s Guide To The Galaxy author Douglas Adams teamed up with Infocom—and specifically, writer Steve Meretzky, one of the company’s more comedy-minded designers—for a text adventure adaptation of his best-selling novels in 1984.

The resulting game is, undeniably, one of the most infamous in this ranking: Deliberately cruel, and sometimes actively deceptive—Adams once described it as both “user-insulting” and “user-mendacious”—while also being brilliantly inventive and funny. How many other games require you to “enjoy Vogon poetry” as a game-winning action? Or get annoyed at you for going into a room it told you not to, and spend several turns lying to you before admitting that there’s stuff in there to look at? Sadly (?), a promised sequel was never completed—although Adams did write a second Infocom game, 1987’s Bureaucracy, which is very nearly as nasty, and as hilarious.

There’s nothing worse for comedy than a good idea delivered abysmally. But such is the fate of the first game on our “Worst” ranking, 2009’s Eat Lead. The premise is brilliant: Matt Hazard is a “classic” video game character who’s about to embark on the latest of what’s supposedly a long line of gaming adventures—only to find his reality collapsing as his publisher starts trying to kill him off. The idea of a long-running game character at war with his own designer, Duck Amuck-style, is brilliant. But Eat Lead never does anything truly clever with it—especially since, no matter what genre the game is parodying at any moment, the basic gameplay remains a very standard first-person shooter. Funny idea: Unfunny game.

By contrast, take 2019 internet darling Untitled Goose Game, which takes an exceptionally basic premise—geese are assholes; you are a goose—and plays it to the constantly honking hilt. The genius of UGG, besides its charming music and visuals, is the license it gives players to be a total dick to everyone they meet. Ruin that gardener’s day. Make that nerdy child cry. Steal that shiny, shiny bell. There are games where you play as actual, world-destroying villains that don’t enable evil as well as this bite-sized, beautiful game does, simply by giving players a “honk” button and free reign to sow havoc on this poor, lovely town, whose only real fault is an unfortunate case of goose adjacency.

It’s a strange quirk of comedy in video games that a title typically has to be fun to be funny. Such is the downfall of Fergus McNeill’s 1996 offering Kingdom O’ Magic, his third video game parody of Tolkien-esque high adventure (after, obviously, The Bored Of The Rings and The Boggit.) And despite a joke-telling style that often rounds down to what we might think of as “sub-Mad Magazine,” Kingdom O’ Magic does have some genuinely funny ideas in it. (For instance: Instead of slaying the local dragon yourself, you put a hit on him with the local “Elf Mafia.” It’s cute!) But despite offering up three different quests, and two playable characters to choose from—a lizard guy named Thidney, or the Barbie doll-esque “Shah-ron The Girlie”—the game doesn’t have enough variety, or enough interesting stuff to do, to justify the player’s time. What’s the point of a couple of good gags if nobody playing will stick around long enough to see them?

There’s a version of this list you could build entirely of titles from the golden days of adventure game studio LucasArts, starting with Maniac Mansion (and its even-better sequel, Day Of The Tentacle), winding through Sam And Max Hit The Road, and dipping in to Grim Fandango at the end. But the core of such a listing would undeniably be the Monkey Island games—and especially the Ron Gilbert-directed Monkey Island 2. Picking up with would-be pirate Guybrush Threepwood now that he is, in fact, finally a mighty pirate, the sequel exemplifies everything great about the LucasArt philosophy: Dense, nested puzzles that demand a mixture of lateral thinking, grounded logic, and just a hint of madness. Wonderfully drawn characters who find a dozen different ways to treat Guybrush with their own brand of cheerful contempt. Gorgeous, cartoonish art. And, most of all, an overall ethos of good-natured weirdness, emphasized by LucasArts’ famed “no player deaths” philosophy.

We’ll admit it: There’s a tiny kernel of a good idea at the core of Pyst. Published in 1996—still at the height of the stranglehold that Cyan, Inc.’s Myst had on the PC gaming world—the parody title reimagines Myst Island in the aftermath of millions of digital tourists tromping all over it, leaving the once-pristine place a garbage-strewn wreck. And sure, there’s a bit of a thrill in seeing some of gaming’s most sacred spaces despoiled with fast food wrappers and cigarette butts. But the fact is that, despite being written by Firesign Theater’s Peter Bergman, Pyst contains neither meaningful jokes, nor meaningful things to do except walk around, click on things, and then move to the next screen. (Which is probably as deep as its critiques of Myst go, to boot.) What it does have is John Goodman collecting what might be the single laziest paycheck of his entire career as “King Mattruss,” decked out in a crown he may very well have stolen from the set of King Ralph, and singing a truly awful song that a) has no jokes in it, and b), isn’t about Pyst. A maddening waste of talent, all around.

The finest-acted comedy game on this list, by far, Portal 2 features medium-best performances from all three of its leads, as J.K. Simmons, Stephen Merchant, and especially Ellen McLain prove just how far a really great voice performance can go. Portal 2 is actually kind of interesting to view in light of this listing of comedy games, because its actual gameplay isn’t funny—joyful, inventive, frequently genius, but not inherently comedic. But the game’s writing, from Eric Wolpaw, Jay Pinkerton, and Chet Faliszek, is so relentlessly snappy and good—and the performances from Simmons, Merchant, and McLain so delightful—that the jokes alone serve as incentive to get you through that next test chamber, just so you can hear another line from energetic mad scientist Cave Johnson, or McLain as a sullen potato.

Released in 1997, Any River Entertainment’s A Fork In The Tale wouldn’t be all that different from a lot of full-motion games of its ilk, with players watching video sequences and clicking arrows and icons to try to keep their unseen player character alive. (It’s basically Dragon’s Lair, except with grainy video footage in place of gorgeous Don Bluth animation.) Except for one thing:

You are Rob Schneider.

Now, despite being prominently featured on the game’s box, the former Saturday Night Live (and future ¡Rob!) star doesn’t feature physically in the game’s video portions. Instead, he’s the voice in your head, constantly rattling off “hilarious” quips every two seconds in response to the mostly generic on-screen fantasy action. (Amazingly, you can often hit a “Funny” or “Wisecrack” button to make Schneider say more things.) The net result is something like watching Mystery Science Theater 3000 if everyone in the theater was Rob Schneider, which is a strong contender for the worst sentence we’ve ever written.

Asymmetric’s Loathing titles are essentially the Airplane! of video games: Fast-moving comedies so relentlessly joke-dense that it doesn’t really matter if a single gag somewhere doesn’t land, because another dozen are waiting right around the corner. Arriving in between the company’s long-running web game Kingdom Of Loathing, and last year’s horror-heavy Shadows Over Loathing, 2017’s West Of Loathing is the most joyfully humor-focused of the bunch. Combining absurd situations—haunted pickle factories! Satanic cows! A literal ghost town powered by bureaucracy!—with a narrative tone that can make epic, loving comedy out of, say, your character’s bizarre obsession with rooting around in spittoons, it’s the rare game that features at least one laugh-out-loud funny joke in pretty much every conversation. Joke writing in games has pretty much never been this good.

A “romantic comedy” that manages to be perversely low on either comedy or romance—but higher than you might like in perversion—1993’s Plumbers Don’t Wear Ties is so aggressively awful, and determinedly unfunny, that we had no choice but to rank it as worse than a game that’s entirely about an unseen Rob Schneider yelling one-liners in your ear. Created by United Pixtures for the short-lived CD-based 3DO, the game aspires to be a sort of playable Skinemax thriller, and can’t even achieve that: Instead, you spend most of your time watching slideshows of somewhat horny pictures while actors woodenly deliver “jokes,” before occasionally being prompted to make a choice. The game dares to ask: Can young lovers John (Edward J. Foster) and Jane (Jeanne Basone) find love and happiness in this crazy world they find themselves in? Christ, we hope not.

If comedy is, at least in part, the art of joyful surprises, then we’re very satisfied to name Twinbeard, Inc.’s Frog Fractions as the finest comedy game of all time. To speak too much about the game would put us in danger of ruining the joke, but suffice it to say that designer Jim Stormdancer’s parody of educational video games goes further, and funnier, than pretty much any other game of its ilk. And the thing is, the laughter provoked by Frog Fractions isn’t just the laughter of a well-delivered joke: It’s also the laughter of discovery, as the player realizes, again and again, that this particular rabbit (frog?) hole goes far deeper than its milquetoast opening might lead you to expect. (The sequel is genius, too, even if finding it might take more work than you might expect.)