I'm going to go out on a limb here and suggest that not everyone would find a "that's what she said" joke all that clever, or even all that appropriate for a business to subtly present on its site.
And I think this speaks to one of the points I tried to make here (http://langer.tumblr.com/post/538680961), which is that ideas like this can come off as witty or clever in such a male-dominated industry because most of us are tone-deaf to the many ways in which another person might find something like this offensive.
My hypothesis is that in order to build a cult following, you sort of have to alienate others. Maybe it's crude, but it's part of the equation. The alternative is to take the "corporate" route and build a boring, conservative 404 that could not possibly offend anyone, but would not possibly entertain anyone either.
If a comedian worried about offending people, s/he wouldn't be funny. If Apple worried about alienating large swaths of the marketplace, it wouldn't have a rabid following.
If there weren't a "positive" effect of alienation, people wouldn't consciously cause it. Maybe it's a side-effect of good marketing. Or maybe it props up the sort of us vs. them mentality associated with cult followings. Or maybe I'm getting too philosophical, and everything I'm saying is bullshit.
Hah - I didn't intend to end 3/4 of my post with question marks. Or did I? ..ahem.
My comment was really a rhetorical question about the moral (not necessarily commercial - I'm not arguing that) appropriateness of taking (as you described) an alienating path.
I've read quite a few descriptions of marketing as being successful by causing unknown wants and needs. None of those descriptions really talk about 'us and them' as a concept.
Full-disclosure: I am both a woman and a Grooveshark employee. Not just employee - Developer.
I read your blog post, and you make some very good points. I feel much the same about the industry as a whole, and became especially sensitive to it after attending FOWA Miami last year, and seeing the vast, vast difference in the number of women in attendance versus the number of men. At the after parties, I walked up to every woman I saw and asked them if they were programmers. I didn't find a a single one. They were all in marketing or design.
But here at Grooveshark? Yeah, so the "that's what she said" joke on our 404 page is inappropriate. But it's still pretty damn funny. Maybe I'm biased. I've heard "that's what he said" jokes thrown about the office as well. As a woman, I'm certainly in the minority of employees here at Grooveshark. But I am absolutely not dumped into any sort of Illustrator ghetto. In fact, I'm the lead ActionScript developer here. The actual Grooveshark application you use every day? Until the redesign, that was all me. It's gotten too large to be maintained by a single dev anymore, but I'm still the one who designs and writes all the application's architecture. I am not sexualized (at least no more than any of the men are) or vilified here. I am a valuable part of our team.
So yes, our industry has a serious problem. But don't think Grooveshark (or our 404 page) seriously contributes to it.
I don't even think it's going out on a limb. Except, of course, it seems to be.
I wonder how many people even realize that the running "that's what she said" gag from The Office is almost exclusively a meta-joke about Michael's constant inappropriateness...
They just don't care and love to have fun, and I love them for it.
My roommate, out of undying love for them, sent their team a case of Brooklyn lager just because. They responded with a full video of someone dressed as a shark as a thank you, and he just got an awesome Grooveshark t-shirt in the mail yesterday. This is how you build cult followers.
It's exactly why I tell everyone around me about GrooveShark if they mention Pandora or another music service. As soon as they get a BB Storm app I may not need my iPod again.
It might be because I have a pretty good screen but I had no need to highlight the header. Still it's clever in its informality, not its technical prowess.
And I think this speaks to one of the points I tried to make here (http://langer.tumblr.com/post/538680961), which is that ideas like this can come off as witty or clever in such a male-dominated industry because most of us are tone-deaf to the many ways in which another person might find something like this offensive.