I think the most brilliant part was the sidebar ad that essentially 'lost' all the space for one arrow. This void completely draws your attention.

The text on the sidebar was also quite clever in referencing itself.

To me, it mostly shows that clever and clear copy wins over nice graphics.

It's not just the void: it's the fact the arrow points directly to the link in the top banner ad.

It's also almost perfect for the audience: it's aimed at cartoonists where intentionally crude stylings are usually intentional. (I doubt it would be similarly effective if promoting SaaS or luxury travel, where it would look jarringly out of place)

It also has a much higher proportion of screen real estate than the average banner campaign and apparently little of visual interest to compete with it, both of which are critical to its success.

yes, but the arrow is much more noticeable with this void. That's what I meant to say.

I did want to mention that the visual style matches perfectly with the target audience - cartoonists. That's a very good point.

I agree it's the perfect mix between content and style. For me it still boils down primarily to great, simple copy.

Ugly ads are sort of known to do well. This is why those "one weird trick" ads do so well. Also the weird sketches of people done in ms paint and junk. It's about getting attention and clicks. And it works.

Ugly ads, long copy, many things still work.

If anyone is interested in learning more about marketing methods, get:

"Tested Advertising Methods" by Caples (be sure to get 4th edition or earlier because later editions have LESS ads!)

Tested Advertising Methods is great.

It's also worth checking out the book Ca$hvertising. Its marketing is exactly as cringe-inducing as it sounds, but it has a lot of solid advice.

Yeah, this makes sense to me in retrospect. As a user of AdBlock[0], I forgot all about those ads. What inspired me was a cheap banner ad for Louis CK's comedy album[1].

[0] I realize the irony. [1] http://goo.gl/SNL3uo

I've installed adblock before because of ugly ads: specifically the "weird trick to get rid of belly fat" with a horrible drawing of... belly fat. (shudder)

A small bit of encouragement - a site I like switched to Disqus for commenting some time ago. Specifically, Disqus with included advertisements. They always seemed to be the same ones, including one with disgusting imagery (I don't recall exactly what, but probably similar to your belly fat ad). Eventually I noticed the link to file a complaint with Disqus... and I never saw that ad on the site again.

The Lessons Learned is the most valuable here. The ugliness doesn't matter, stand out and address your potential clients on their level.

Yup. Ugly works extremely well.

I've personally made significant money from a very similar ad. Never underestimate the power of MS Paint (or equivalent)!