Last week I posted a toon about Twitter selling ad space on the Fail Whale. At the time it was just for fun, but a few days later I started to wonder if Twitter should consider it a legitimate revenue opportunity.

Though the frequency is a lot less than in the early days of Twitter, I still get a visit from the Fail Whale several times a week. And if I see it, so do millions of others who are on Twitter at that time. That smells like an opportunity to me.

Now the question is who would buy an ad on the Fail Whale and what would they be willing to pay for it? I asked a few ad people and also posed the question on Twitter.

Jason Falls, a former ad guy at Doe Anderson, pretty much captured the prevailing opinion:

“I think selling ad space there would be dumb. It’s monetizing your screw ups for nothing more than monetization. You don’t want the Fail Whale to show up. If you did, you’d make the system crash more often, which would drive users crazy. Wait, Twitter does that anyway.”

However, there were a few brave thinkers who thought it might work given the right brand and/or product and, of course, the right sense of humor. This is where I think the opportunity lies. Why not market the Fail Whale ad space to companies whose products or services address failures?

For example: say you work at an auto repair shop like Meineke that either fixes failures (e.g., brakes) or tries to prevent them (e.g., regular maintenance). An ad on the Fail Whale could serve as a clever way to get that message across to millions of people. Imagine a text bubble coming out of the Fail Whale’s mouth or blowhole with the message: “Check your brakes or die! [insert company logo and link].” Sure, it wouldn’t be easy to pull off. But I think many ad agencies would love the challenge (e.g,. Wieden Kennedy).

Would people be annoyed? I don’t think so. At this point, most people have come to terms with the Fail Whale. There’s even a Fail Whale Fan Club with thousands of members (you can even buy Fail Whale products). But, even if you were annoyed, would it be enough to make you delete your Twitter account? Of course not.

So what could Twitter charge for an ad on the Fail Whale? I’m still waiting to hear back from the ad experts on that one.

I, for one, hope Twitter gives some serious thought to this idea. After all, hasn’t the poor Fail Whale suffered enough. Give the Fail Whale a chance to become the “Cash Whale.” It’s the right thing to do.