Would it be possible to add humor based flagged questions that are not serious in nature, not quite open threads, but would be variations on a theme, just to get the crowd sourcing response. Something like "Did Hillary just get schlonged by Weiner?"
No, because this would contradict the very nature of StackExchange.
We are here to learn. To learn from facts, not from someone's sharp tongue and a quick wit.
There are plenty of political-related chat boards and forums around, and humorous posts here would only dilute the valuable information.
Exceptioุุุุ้้้ns from this rule are very rare. :-)
The closest thing I know of on a Stack Exchange site is Mi Yodeya (Judaism) and their Purim Torah policy. As part of a cultural tradition, they have a few weeks out of the year where they can ask humorous questions, but only with strict guidelines about the nature of the humor (e.g. a misinterpretation of the Torah).
If we allow political humor, I think we would also have to set guidelines as to what kinds of humor is allowed (we don't want rude or offensive humor. I also think it would be a difficult to moderate.
Additionally, we don't want to change the goal of the site. Mi Yodeya is primarily a site about serious questions, so Purim Torah questions must be closed at the end of the allowed period. I think that this site is about serious questions, so we don't want to encourage it to become a humor site.