Saturday during the Hothead panel someone mentioned that in one of the QA panels Jerry and Mike had talked about wanting to do a Paint the Line video game, which got me to thinking about how I would approach that game, and then to what other sort of weirdness could be drug from the depths of Penny Arcade weirdness into the world of video games. I am probably one of the few Penny Arcade readers that often prefers the tangents and diversions over the bulk of the daily strips, and I always find it funny that they apologize profusely for them.
Paint the Line, Penny Arcade's recent pastiche of 80s sports films about Ping Pong versus Communism, is the easiest to pitch as an insanely fun video game: focus on Wii development and put that ole wiggle and waggle to use in "Nearly Realistic Ping-Pong Action". It just about sells itself right there. License Final Countdown and maybe get Freezepop to do one or two other songs for the game and you've got retro-themed gold. I would even do it episodic with an epic story and call it Paint the Line: The Series, making it further a satire of television adaptations of a cult series of movies. You get a free explanation for why Gabe and Tycho only have cameos: the television production budgets couldn't afford them. Instead the player gets the opportunity to field a duo of two young upstarts upon whom the mantle shall be passed. I think it would be awesome to build it as something of a two-player co-op Ping Pong adventure. For each episode you would have two Tournament Paths, A and B, and a player could play each inter-twined or a duo of players could tackle A and B simultaneously with somewhat harder cooperative puzzles and possible an extra Tournament Path C with doubles rounds.
Cardboard Samurai I expect has a large enough following clamoring for a video game that I can skim over it. Some would want Wii MotionPlus sword fighting, but I think it would be more interesting to use JRPG gameplay like PA:OTRSPOD, but with the opportunity to more closely satirize JRPG conventions. In particular I can see wandering a mountain capped with both snow and zen-like calm and experiencing random encounters where the scenery changes entirely to a volcanic desert and you fight lava men or something. Random encounters are just weird, but this gives you the opportunity to explore the random encounters as potentially flashbacks of battles or, more intriguingly, battles with ones own mental demons.
But what keeps me reading Penny Arcade is Twisp and Catsby. I could see a deep series of Twisp and Catsby "minisodes". Build 30-45 minute episodes of wildly abstract puzzles, flirting with the very illogic that adventure games fight spiraling toward, wrapped around some creamy nugget of an infinitely replayable casual game, such as match-3 with fish and tea crackers or breakout with a parasol and raining frogs, loosely connected to the apparent plot of the episode and maybe necessary for some small puzzle goal, but playable without touching the story. Let the casual game be the focus: don't number the episodes, give them wild sub-titles and then let them be known as "The One With Breakout", and then you can have fun letting players wonder about the true chronology of the episodes. With the focus on the mini-game you also can play more with the structure of each game's plot, ending most without any real sense of resolution or starting with a climactic action sequence and then sulking into brooding tedium; foreshadow existing episodes and reference future episodes and just generally have fun with the form of the narrative. But, get people to come for the mini-games and stay for the wild narrative.
Then allow the various mini-games to voltron together into some bizarrely abstract Puzzle Pirates with the mini-games acting as some sort of weirdness economy and having direct and indirect effects across the series, possibly hinting toward some deeper meta-puzzles.
Finally, I'll only briefly mention The Merch (which has been my Gamerpic for a while and is fun to explain to the uninitiated; it's all cute and smily but deranged and evil and keen insights like "I fucked your dad!", which is so Xbox Live), but needless to say I'm sure there are people that would easily appreciate an M-rated Pokémon or collectible card game with endless DLC...