The problem with crazy campaign ads like Elbert Guillory's Coconuts thing here is the cynicism has sucked the joy out of them. Sure, there's always been a degree of calculation in offbeat political advertising. But what we're seeing here is a different level of manufactured intentional post-modern schlock.
Guillory's ad isn't a happy accident of charming "Special Man" type eccentricity. Instead, it is the product of well paid mainstream communications professionals acting well within the scope of their current best practices. Remember earlier in the Presidential primary when Buzzfeed was producing these quirky viral videos of Republican candidates? Pretty likely the purpose of that exercise was getting some creative interns a chance to test the viral political ad as a form while also padding out their own resumes in the field. Being WeirdTM is really just plain old formulaic marketing now.
While colorful characters have long been a part of our politics, the Palin-Trump age has shown us that outrageous behavior for its own sake is actually a potent brand. Anyone managing Elbert Guillory's campaign will know this. So get ready for more affectedly bizarre ads. The PR puke funnel is bound to have plenty more where that came from.