I'm reasonably sure the most obnoxious douchebag of 2007 was Chad, the Alltel mascot.
The Alltel commercials began innocuously enough. They had Chad, and then all the other cell phone mascots, talking and Chad explaining why Alltel was better. This was acceptable he was not annoying and the commercials were kind of clever if only because of how well they approximated the other mascots.
The first sign of trouble, however, was the fact that the dude was named Chad. I refer you to Figure 1.1, a Venn diagram showing why this is the case.
As you can see, there's no room for the possibility for him to not be a douchebag. This becomes apparent when they abandon the other companies' mascots in favor of the personification of them as nerds.
Clearly, I am going to have a problem with this.
See, I don't necessarily like nerds. Often, they are egotistical assholes. But I am one and I like douchebags even less. The personification of the other companies has caused me not to dislike them but to sympathize with them.
Does anyone really like guys like Chad? I posit no. Not when they don't have to. And so begins a series of commercials where the nerds try too hard to keep customers via ill-conceived and destined-to-fail dastardly plots while the suave Chad stands by and wins customers on sheer charm. It's obnoxious as hell.
It's a high school fantasy come to life of being the super-cool dude with the perfect blonde hair and blue eyes (HURR NAZI HURR) who gets the cheerleaders (there is a commercial where this actually happens.) Alltel wants to be that dude so bad. That dude is a world-class dick.
So, I will say this. If anyone wants to make me a billionaire, I will track down every single Alltel customer. I will find every person who uses it. And I will pay them cashy money to switch. Switch to anyone else. I don't care who. I will throw in a free iPhone. Alltel deserves to crash and burn.
Because Dungeon Masters don't have levels.