Crapshoot: Microshaft Winblows 98, the parody that forgot the jokes

From 2010 to 2014 Richard Cobbett wrote Crapshoot, a column about bringing random obscure games back into the light. After seeing the name of this week's bit of obscura, you should know all you need. Stick around though. The Muppets turn up near the end. Honest.

Drinking leper vomit. Being served a beloved pet in a bun. Being dragged naked on train tracks sprinkled with salt and broken glass. Drowning in a vat of live maggots.

Oh, hello there, readers. You just joined us, the PC Gamer team, in our weekly game of "Things That Are More Fun Than Microshaft Winblows 98". We've been playing it for the last decade and a half, for an hour a day, and unlike this terrible excuse for a CD-ROM, we never seem to run out of material. So far, only three things have been disqualified for going too far: the movies of Seltzer and Friedberg, a dentist getting the hiccups during root canal surgery, and the other parodies from creator Parroty Interactive: Star Warped, The X-Fools, and one of the few games to specifically spoof another: Pyst. Shudder.

Microshaft Winblows 98 is content to be the funniest thing this side of spelling Microsoft with a $ in the middle. It's not really a game, although it has a few of them in it, but more of an interactive comedy CD-ROM. The premise is that two Microsoft employees, Meg and Graham, have secretly put together this game to break into software development—Meg to stick it to the Man, Graham to gently poke fun at his idol, Billy G—and somehow you've found it on the network. Your challenge is to climb your way up the corporate ladder from the Tech Support department all the way to a meeting with Bill Gates himself, enduring enjoying riffs like the Microsoft slogan being "Who Does He Want To Own Today?"

CLARIFICATION: Yes, that was supposed to be funny.

Almost from the start, you can smell the desperation. Winblows feels like a game that was agreed on, everyone involved high-fived each other, sat down to work, and froze as they realised how little material they actually had to work with. In fact, I imagine it going a little something like this.

"Okay, so what's on our hit-list? Thing #1: Bill Gates is a nerd. Everyone OK with that?"

"Definitely comedy value there, yep. And Microsoft... well, everyone knows they like money."

"Not sure we can fill a whole disc with just corporate jokes. I know, let's do some hilarious TV parodies!"

"Awesome! Um... how about Star Trek? Only instead of Trek, we'll say... Tech. Star Tech!"

"Brilliant. Go write it. Don't make it too funny though!"

"Well, you definitely didn't make it too funny. Well done."

"Thanks. OK, we've used up our most obvious joke, and now we need nine more."

"Oh, Christ, I don't know. What's that popular show with the friends?"

"Friends?"

"Yeah. Do that, only... they work at Microsoft now. Or something. We'll be fine, just as long as we come up with a really clever, imaginative name to set up the hilarity."

"I just felt my soul leak out of my anus."

"You're a comedy writer. You won't need it."

Most of the parodies on offer suffer not just from being about as funny as waking up in the morning to find you've suddenly got your mother's herpes, which is admittedly a fairly serious flaw, but being incredibly tenuous. "Xena: Code Warrior" is a lazy idea, but you can at least vaguely see how it came together. "Mister Gates' Neighbourhood" is a reasonable concept. But "Bill Watch" instead of Baywatch? "Touched By Bill" instead of Touched By An Angel? Stop! Parodies do not work like that!

(At the very least, they could have been "Touched By A Nerd" and "Elliot Baywatch".)

It doesn't help that Winblows is stuck mining geek humour almost exclusively, rendering many of the jokes that do work (I counted about three) more a case of 'Oh, OK, yes, that was fairly clever' rather than actually laugh-out-loud funny. Most of the time, it smacks of non-technical people desperately trying to write jokes in what may as well be a foreign language, and sounding about as convincing as your average Oxbridge politician trying to 'get down' with his 'homies' in 'da hood'. In the intro alone, Graham tells a suddenly worried Meg, "They could never fire you, my little megabyte," to which she wittily replies, "Call me that again and I'll rip out your modem." Good grief. Cue the tumbleweed of failure...

The basic game is that you watch everything on offer, then an email arrives with a cryptic password hint that lets you into the next level, which unlocks more stuff. The different sections are CampusCam, where you watch lousy security camera footage, the MSTV Network with the above parodies, Bill's Personal Outlook with some uninteresting diary entries, and the Reject Bin, which shows some appallingly rendered box-shots of failed Microsoft projects like the 'Live Mouse' and 'Naughty Net Nanny'. They don't even pretend to have taken the time to make them look like real products, never mind Microsoft ones.

For educational purposes, here's the exact same basic concept done much better in Space Quest IV - real parodies (although obviously dated now - the game came out in 1991), descriptions that actually build on the title gags, and art that bothers to help the humour out instead of leaving it to die alone.

By far the most painful parts of Winblows 98 though are the mini-games it throws in. Think of Windows. What are the traditional games provided with it? Minesweeper. Solitaire. Drawing willies in MS Paint. Obviously, Winblows serves up hilarious parodies of all of these to...

...wait, one second. I'm pretending to be told something I clearly already know...

...nope, none of those are in. Instead, your random parodies are a board game called The Roll Ahead, based on Gates' book "The Road Ahead", in which Bill Gates and Steve Jobs race by rolling a die and making you wish you could just do exactly that. There's Pinbill, which actually isn't much worse than the actual Microsoft pinball game, even if its only real joke is Bill having a large nose, which he doesn't, Winblows Exploder, which may be one of the worst shooters ever, and... Win Bill Gates' Money.

This one is just weird. It's based on a show called Win Ben Stein's Money (which came out in the UK as Win Beadle's Money), but doesn't use its format. Instead, it's a blatant, unfunny, and above all else, incredibly cheap rip-off of the excellent quiz series You Don't Know Jack. (I was willing to write this off as a coincidence until it actually namechecked it during one of the questions.) It's so cack-handed, it doesn't bother randomising the questions, just which chain of them you get. It's so lazy, there isn't even a custom line if you don't bother answering—when the time expires, it just acts like you chose the wrong answer. It's so awful, it... it really sucks ! What's more, Monty Python's The Meaning Of Life comedy interactive kinda-game had already done a rubbish You Don't Know Jack parody the year before.

Even if we ignore all of that though, just look at this! People were paid to make this!

There's a reason there weren't many games like Microshaft Winblows 98, beyond the fact that we live in a world where concepts like hope and sanity exist. Even if you had the requisite lobotomy to find them hilarious, there was never much content for your money. You can see everything that Winblows has to offer in five minutes, and the rest of its videos in a couple of hours. Not even the game part slows you down, since there's nothing more to it than working out a password, and if you don't guess that "PAMELA ANDERSON'S CLEAVAGE" should translate as "SILICON VALLEY", Meg and Graham only let you give two wrong answers before just telling you what to type and calling you an idiot. They also call you an idiot if you don't move the cursor for more that 0.2 picoseconds and for a few other things... up to, but not actually including, installing and playing this worthless game. The one time it would be deserved.

But maybe it's not Winblows 98's fault that it can't even get close to comedy without being slapped with a restraining order. Maybe Windows and geek jokes just aren't funny enough to carry a CD-ROM.

Or maybe... just maybe... it's all a question of how you tell 'em.

Muppets Inside was released in 1995, but still makes Winblows 98 look older. The premise is that the Muppets are trapped in your computer and need your help to escape—in practice, by joining them on a tour of your own motherboard. As a game, it's nothing to write home about, made up entirely of simple challenges that just repeat and repeat and repeat ad infinitum.

As a geeky comedy experience though, it wins out over Winblows for one big reason—it feels comfortable with its material. There's plenty of new footage, lots of clips, but more importantly, lots and lots of genuinely funny bits and pieces, from the hyper-geeky jokes (you get around the computer by driving a 'Data Bus') to the completely random asides like Rizzo singing a song about Jim Henson trademark enforcement to the tune of Carmen's Toreador song. Most importantly of all though, there's this:

The limited number of games on offer quickly get a bit dull, and none of them are much fun. The style and humour carries it much further than any similar game though, with by far the most memorable bit being its intro. I won't spoil the details, but this is how you do a geek joke, Winblows. Watch and weep:

HISTORICAL NOTES: Since Winblows' release, Bill Gates became the biggest philanthropist of all time, the Office Assistant became the most hated thing to appear on a screen since Scrappy Doo, and Microsoft even released its own joke version of Windows: Vista.

Nobody laughed much at that one either.