Actually, the Leno thing isn't the worst strategy. It is appalling how many Americans obtain their political opinions by watching to see which politicians Jay Leno is skewering, by watching Saturday Night Live and seeing which politicians are being mocked, and/or by watching The Daily Show or South Park on Comedy Central. There is no depth to their opinions, only a general impression created by these kinds of shows. Why do you think that candidates try to get on shows like Leno, Oprah, SNL, and the Daily Show? Sad state of affairs, really...
It may not play well with hard core political types, but I think it will go over well with the average Joe Sixpack.
After a few months of campaigning and a coupe of debates, this will be mostly forgotten.