It wasn’t exactly a surprise when LucasArts got out of the quirky point-and-click adventure business and strictly into the Star Wars business, with a dash of Indiana Jones for flavor, but there was always that question mark of what LucasArts designer Tim Schafer, one of gaming’s most unique voices and the creator of adventure game classics like Full Throttle and Grim Fandango, would do next. It took five years to find out, but the studio Schafer founded, Double Fine, immediately set itself apart with its debut title, Psychonauts. . With a 20 year legacy, it’s time to take a look at Double Fine’s entire body of double-fine work, and judge which ones were double-finer than the others.

We only have a couple of tiny caveats: One, we’re only looking at the stuff Double Fine developed itself. Yes, the studio has published some wonderful stuff–not nearly enough of you played Knights and Bikes, and we’re still bitter about it–but, still, not Double Fine’s game to claim. Second, as the title says, we’re only looking at major releases. So, the smaller stuff developed for Amnesia Fortnights or for Kinect don’t count–though any Sesame Street: Once Upon A Monster slander will not be tolerated. Lastly, including the LucasArts remasters feels like a cheat, so they’re not here. We will say “remake Maniac Mansion” just once, and leave it at that.

With all that in mind, let’s have a look.

For all the wailing and gnashing of teeth that came from the realization that Brutal Legend was a strategy game, Double Fine’s actual full-throated swing at the genre, Massive Chalice, is commendable, but ultimately kind of a whiff. You play as a monarch whose lands are besieged by a legion of death-bringing creatures called the Cadence. The titular massive chalice and the dueling deities therein can wipe out the Cadence, but they’re on Dragon Ball Z Spirit Bomb time, so, it’s up to you and your progeny to hold off the Cadence for literal centuries until that day.

A big part of it is its sheer difficulty, and having to throw so many soldiers at a problem that the game’s other mechanics fail to mitigate. But these types of games tend to live and die on making you care about everything else, the framework of the thing, and aside from the expected snarky sense of humor peeking out from time to time, Massive Chalice doesn’t have nearly enough going for it there, either.

Best Moment: Well, Massive Chalice isn’t exactly a game of moments like that, but for what it’s worth, the lineage system is forefronted here in a way that doesn’t always get the same TLC in other strategy titles. So, there’s that.

Despite being a full game, Rhombus of Ruin was the coinflip in Double Fine’s resume in terms of whether to include it. It’s more of a fancy bridge title that was meant to tide us over till Psychonauts 2, and a nice little VR experiment–all the Psychonauts characters we know and love are in there, and getting to hang out with them in VR on a rescue mission into a psychic Bermuda Triangle was definitely a pleasant surprise. That said, it’s also kind of a nothingburger in terms of gameplay, and even if you took your sweet time, this game’s only about two and a half hours long. Let’s call it a wash. It’s a nice thing to experience once (especially since the ending leads right into Psychonauts 2), and then never think about again.

Best Moment: The sequence where you get Dr. Loboto’s full backstory feels like watching Coraline in VR. Best part of the game, and it’s not close.

Broken Age was meant to be Double Fine’s triumphant return to the point-and-click adventure genre–the genre made many members of the development team famous–and old-school fans were behind the developers whole-heartedly to the tune of millions upon millions of dollars on Kickstarter. And in Act I, it almost is the triumph that was promised, with a simple but all-too-relatable tale of two teenagers, Shay and Vella, trying to figure out how to rebel against the forces of patriarchy and parental neglect from two different directions–one a medieval fantasy, one in a sci-fi dystopia. The whole thing collapses in Act II, though, where subtlety gets sucked out an airlock, our protagonists go to stupid lengths to save each other despite never sharing a space together, and mighty God, so many wire puzzles. SO MANY. By the time the ending just sort of happens, the game’s well of goodwill is fully empty. And that’s a damn shame.

Best Moment: The ending of Act I, with Shay and Vella switching places, is subtle and wonderful in a way 90% of Act II just isn’t.

Double Fine bringing LucasArts alum Ron Gilbert (of Maniac Mansion and Monkey Island fame) back into the fold sounded like it could’ve been a big Return of the Mack moment for the studio. The final product falls a bit short of that. It should be a pretty simple adventure game, with a little over a half-dozen weirdos gathered from across space and time to a mystical cave to reflect on their sins, but because there’s no inventory system, schlepping one object at a time back and forth across stages becomes a pain in the ass, and to see everyone’s ending, you have to do it multiple times. Basically, in trying to make a fast-paced point-and-click game, Double Fine made a slog of a puzzle-platformer. And yet, even still, it’s a Ron Gilbert joint–the man’s creativity and sense of humor make every annoying step of the journey worthwhile. And with a little over a half dozen characters to spend your time with, there’s still plenty of incentive to go on this little adventure a couple of times.

Best Moment: The constant “oh, she’ll be fine” after the dragon is let out and we hear nothing but the damsel screaming is hilariously grim.

Rad technically has all the right elements to be an absolute hidden gem of a roguelike, from the sense of humor, to the wide swaths of ’80s nostalgia, to the story actually having more going for it than expected–with a tribe of irradiated mutant kids trying to figure out their place in the post-post-apocalypse–to some wildly imaginative mutation upgrades. The only real issue is that it’s terribly unbalanced, and there’s so much work involved for rewards most other roguelikes offer a lot more freely. You could be wandering from settlement to settlement, splattering gross abominable mutants with an assortment of garage-sale appliances for hours before you wind up with an actually useful upgrade, all while 3 or 4 hits can end you in 30 seconds.

Best Moment: There’s a bunch of the mutations and townfolks’ reactions that are priceless, but the best and simplest one is right at the start, when you find out humanity’s collective reaction to a second apocalypse happening in the apocalypse is “….seriously?”

In a continuing trend of Double Fine defying the trends of the moment, around the time when Lego games were all the rage, Double Fine decided to make a game modeled after 1920s silent movies about the evils of capitalism. It features an all-star cast of Russian nesting dolls, their patriarch kidnapped and forced into indentured servitude, and the youngest of them determined to punish the bourgoisie to get him back. Matryoshka dolls as a metaphor for class struggle is built into its puzzle game mechanics. That’d be a big swing now, let alone in 2011, but despite being painfully short, Stacking is just too damn funny and charming to deny.

Best Moment: When you finally take down the evil baron, and a pit full of adorable moppets rips him to shreds. Oh yeah. That’s the good stuff.

The folks at Double Fine have never lacked for amazing high concepts for games, even when the end result doesn’t quite hit, and that goes for big-budget titles as well as small, low key indies, such as this one made for Adult Swim and their sadly defunct games division. You’re a disembodied head in a helmet in a ’70s-style sci-fi future, and in order to save humanity from being trapped as robot slaves aboard a giant spacecraft, you’re going to have to jump from body to body to kill an evil supercomputer. The weird irony is that while the game is massively fun, and often funny, it often feels like it was supposed to be even funnier and cruder at some point–it was, again, an Adult Swim Game, so that would make sense. From the not-even-suspiciously phallic spacecraft, to the constant, deadpan innuendo, to the weird VR pleasure port early on, there are areas where Headlander leaves jokes on the table. Considering the tradeoff is some of the tightest gameplay in a Double Fine game, though, that might be a small price to pay.

Best Moment: The action setpiece in which you must defend the Rogue Eye, where the action slows down to Zack Snyder speeds and a Karen Carpenter-y ballad plays.

The main takeaway from Costume Quest 2 is that Double Fine hates dentists. Like, not just in an “ugh, time for my appointment” way, but in an “these people are evil and must be destroyed” way. As such, putting our two young heroes up against a time-travelling dentist, whose ultimate goal is to create a dental dystopia based on mouth purity, feels like somebody has missed a few therapy appointments. It’s still the newest, and most unique part of the game. In every other regard, Costume Quest 2 is much the same as the first–a turn-based RPG, in which kids use a variety of Halloween costumes to take on different powers. That’s not necessarily a bad thing, even if it stretches on a bit longer than necessary. It’s a nice little confection, but as opposed to the first one, by the end, you’re definitely ready for a vegetable or two.

Best Moment: The fascist dental academy is a strong contender, but, nah, the correct answer is the Candy Corn costume. Candy Corn is useless, everyone knows it, and Double Fine built a whole gameplay mechanic about it being useless. This is righteous and just.

Possibly the most infamous bait-and-switch in gaming history. Jack Black playing the world’s greatest roadie getting isekai’d into a harsh heavy metal universe is a slam-dunk of a concept. What starts as–and was sold as–an action-packed open-world heavy metal beat-em-up reveals its true identity a few hours in as Baby’s First RTS, and the audience that came for the former would never forgive Brutal Legend for being the latter. That’s definitely a miscalculation on Schafer’s part, and the sense of betrayal is valid, but over time, it’s hard to stay mad. The relative ease of the RTS portions made them go down easier, and the game’s core idea of making these epic battles feel like unleashing an army of mosh pits–a tornado of souls, one might say–does land once you’ve gotten leveled. For metalheads, no other game has ever committed and delivered so hard on its premise. This is a world where Lemmy is a bass-playing healer, where Rob Halford’s powerhouse of a voice can murder you, where you can ride around in a monster truck to one of the most extensive and well-curated metal soundtracks ever collected for a game, and where every single area of the world looks like a Death album cover. It’s a good little game that never got a fair shake.

Best Moment: The final boss has you killing a demon emperor voiced by Tim Curry with an electric guitar while Judas Priest’s Painkiller plays. How dare anyone slander this game.

It’s weird thinking about a time when a tiny little indie RPG felt like such a simple, sweet novelty. Now, six of ‘em probably hit on Steam while you were reading this sentence. Costume Quest is still one of the greats, though, a sugary-sweet little flight of fancy about two kids who get swept up in a supernatural adventure while trick-or-treating, and discovering their adorable homemade costumes can come to life. It’s fun, frequently funny, and imaginative, and if you didn’t have a bag of candy in your house before you started playing it, you’re gonna wind up with one after, and that bag will last approximately 20 minutes after that.

Best Moment: It’s the dumbest, easiest joke in the game, but one of the Vampire costume’s abilities being called There’s A Bat In My Hair is funny every single time.

In a gaming landscape where platforming collect-a-thons were as mindless as they come, and everyone was looking for the next Mario when even Mario wasn’t at his peak, Psychonauts, a platformer following a big-headed psychic named Raz as he runs away from home to find his people at a summer camp for psychics, felt like the way, the truth, and the light. Mechanically, it has aged some, but even its shaggier parts are brimming with imagination and charm, and the ensemble cast is absolutely unforgettable even 20 years on. But moreover, the game is just funny as all hell, following even its dumbest puns as far down the comedy rabbit hole as they’ll go, without edging into cruelty. Raz’s little psychic summer camp adventure and all the color and wonder therein have been a place worth revisiting time and time again.

Best moment: Once upon a time, the answer would’ve been Lungfishopolis. We were in a kaiju film desert, and someone keeping the faith on the giant monster front was heartwarming. With time and distance, though, in 2025, it’s Raz’s father showing up to sort through everybody’s daddy issues with him.

When the first Psychonauts hit in 2005, it launched in a kind of low point for the 3D platformer genre. While Psychonauts was sloppy in its way, it was so full of great ideas for how to make every aspect of it meaningful, it was still a work of art. Psychonauts 2, even with its absurdly long development period, launched in a time of great creative abundance. And it still managed to shine, the game absolutely bursting at the seams with meticulous details and symbolism. It even went a little darker than expected , with its main plot tackling generational trauma, and the effects of fascism on a populace. Somehow, it does that, effectively, while still maintaining a cheery, day-glo tone and aesthetic. The wait was more than worth it.

Best Moment: You could populate this with just snippets of NPC dialogue, and any of them would be correct. But no–Raz’s grandma giving him “everything I’ve got” for the final boss fight, and the hug after, wins this.