Anyone who knows me well will tell you I spend time reading, thinking and talking about design and movies in almost equal measure. So I hope that explains why I might share this seemingly incongruous link to an essay about the controversial '70s film, Caligula.

Caligula is not the sort of movie people discuss at work, and by extension they probably shouldn’t blog about it either. But this essay’s larger theme is the real reason I read it and am sharing it now: It’s about the importance of taking risks and failing. And one line in particular really sums it up: “Caligula failed. But that epic failure was braver, and more significant, than a thousand mediocre successes.”

That got me thinking about big failures in branding that have happened in the last few years. Tropicana’s attempt at rebranding and packaging comes readily to mind. As does Gap's disastrous new logo, which they quickly rescinded. And looking further back, New Coke remains a classic case. Most designers would quickly lump in the rebranding of AT&T, Xerox and UPS (among others), but none of these reached the same level of public outcry and arguably can’t be counted as flops in the same way.

Regardless, none of those failures can be compared to Caligula’s, because that film had something they did not: ambition. Granted, its ambition strikes most folks as unwholesome, but its intent was to challenge convention and that is commendable. Caligula was crippled by the hubris of its creators, but they courageously chose to zig where others zagged. By contrast, the new Gap logo was a product of meekness and mediocrity, crippled not by zigging, but by zagging harder.

And so I’m left to wonder when the world of branding will see its own Caligula. A failure that is brave, unapologetic and truly challenges expectations not only about the expression of a brand but about what constitutes effective—and yes, beautiful—communication. I have at least one candidate in mind.

Next year London hosts the 2012 Olympics, for which Wolff Olins designed the graphics. It has been a widely derided campaign, a failure by most industry (and civilian) accounts, but they have marched ahead with it nonetheless. And so it may be that the only way we can deem the London 2012 graphics a worthwhile failure is if, at the end of it all, they win everyone over, thereby making them a success. The promise of such a paradox may prove to be the most entertaining sport of the summer, as far as I’m concerned.