Comedy Central's Jon Stewart announced Thursday that he'll spearhead a rally in Washington, D.C. on Oct. 30 (Stewart, perhaps jokingly, said it might be called "The Rally To Restore Sanity" or the "Million Moderate March").

It'll be a fun day, for sure, even if you don't like Stewart's politics: Washington rallies tend to be more serious than silly. But Stewart has a serious message here: Just days before the midterms, Stewart aims to prove that America's collective moderates can drown out the extremes who can dominate political discourse (and his own show's skewering...) from time to time.

Stewart is a media darling and his event is sure to be heavily scrutinized, so we might as well get the ball rolling with five questions we'll be looking to answer come Oct. 30.

1.) How much of this is clever book promotion?

No one doubts that Jon Stewart passionately - and genuinely - believes in the views he espouses on his program. But skeptics might note the timing: Stewart's October rally comes just a month after the release of his new book, "The Daily Show with Jon Stewart Presents Earth (The Book):

A Visitor's Guide to the Human Race". Stewart's last tome, “The Daily Show with Jon Stewart Presents America: A Citizen's Guide to Democracy Inaction," was a massive best-seller and there's certainly hope that this one will be, too. Stewart has already announced high-profile media hits timed to his book's publication: Stewart heads to NBC's "Today" show next week and Fox News' Bill O'Reilly will visit each other's shows in late September.

2.) What if no one shows up?

We're kidding obviously - Stewart and Colbert both have enormously loyal followings. But you can already predict one media narrative:

Will the Stewart/Colbert rallies eclipse the crowd summoned by Glenn Beck at his August "Restoring Honor" rally? If so? Mission accomplished ... and it would be a massive coup for Stewart, Colbert and their fans that their message of level-headedness bested passionate partisans. But, we've seen young generations (a key Stewart/Colbert demographic...) fail to meet exceptions in the past when it comes to political involvement and a sparse attendance will quickly lead to, "If Jon Stewart can't do it, who can?" headlines about Democratic fortunes, just days before the midterm elections.

3.) How to handle the "Colbert Factor"?

Stewart skillfully walks the fine line between comedy and contemplation and the audience allows him to straddle both. Colbert, however, plays a conservative on his program, even though his audience knows he's joking. Still, soundbytes are soundbytes. Where a solo Stewart rally would pit him and his message against the nation's extremities - the goal of this effort, it appears - a Stewart/Colbert dichotomy would, in part, move the focus away from the issues and on to their addictive and humorous dueling rapport. It could become less of a Jon Stewart rally, than simply another Stewart/Colbert comedy show.

4.) Will there be another competing rally?

When Glenn Beck announced his rally on the anniversary of Martin Luther King's "I Have A Dream" speech, Rev. Al Sharpton quickly put together a counter-rally. And, if a true conservative (not the Colbert variety...) wanted to challenge the Stewart/Colbert monopoly on the National Mall that day, it'd be hard for the mainstream media - who are already accused of being both left of center of Stewart/Colbert admirers - not to give them plenty of airtime (even if disproportionally so...).

5.) Will Democrats really benefit from this?

Sure, the rally's ire is aimed at extremes on both the right and left, but it's no secret that both Stewart and Colbert are left of center.

So, regardless of how many Republican notables are persuaded to appear at the rally (might Stewart get his wish and convince Sen. John McCain to appear?!? http://www.tvsquad.com/2010/09/10/jon-stewart-misses-john-mccain-gives-daughter-meghan-a-letter-f/), it'll still be perceived as a midterm rally for Democratic causes.

But, as the Huffington Post's Jason Linkins noted on his Twitter page just moments after Stewart made the announcement Thursday night, "Uhm, seriously, people, if your entire GOTV effort was entirely dependent on late night teevee comedy fans, UR DOIN IT WRONG. #perspectiv." It's a fair point and, since Democrats are already perceived as the party of Hollywood celebrities and Manhattan elites, this rally could very well also motivate conservatives to the polls who just hate that aspect of the Democratic Party.