Michael Dukakis was a Democrat candidate running for President in 1988. He had previously been criticized as being soft on national defense, so in September of that year he orchestrated a photo op in an M1 Abrams tank meant to toughen up his image.
The public found the image of Dukakis in the oversized safety helmet comical, and the photo op had the opposite of the intended effect of making him look tough. So much so that his opponent, George H.W. Bush used footage of Dukakis' tank ride in his own advertisements.
Ross Perot was never going to win. Especially after dropping out then rejoining. He said dirty tricks party threatened to out his daughter which came off weak instead of just saying "Republicans"
Al Gore - Bragger
It was Al Gore is a bragger for saying he invented the Internet. Which he didn't say, and Vint Cerf repeatedly defended Al Gore as the only politician who saw the potential of the Internet and worked to make it happen.
Mitt Romney - Binders full of women