Will it work? It’s hard to say. I’m thinking that it’s pretty much unprecedented in presidential elections, but it’s certainly grabbed a lot of attention during what is traditionally a very slow period in the presidential race, and people do appreciate a sense of humor (I think that John Kerry’s tendency to take himself far too seriously certainly worked against him last time, and we all remember the wooden Al Gore.) Of course, Bob Dole is a very funny guy (I doubt that he does the late night shows anymore, but when he did, they were a riot), but I don’t think that he ever attempted to capitalize on that during his campaign.
Plus, there’s this:
The laugh-laced attacks have offered Democrats an unappealing set of options:
Respond to the substance of the criticism and look humorless -- or play along,
and risk permanent laughingstock.
I think that Dems have risked appearing humorless a lot lately, pretty much since they got the reputation of having to make everything PC, so this might really play to that.