Well, first off, Dole had a dry sense of humor and fathomless sense of irony that Romney would not and could not even comprehend. But Steve Kornacki draws the parallel:
Like Obama, Bill Clinton began the 1996 cycle on the heels of an epic midterm election defeat and with the opposition party convinced it had found the formula to defeat him. But the Republican Party’s image plunged in 1995 and early ’96, the product of overreach by its new congressional majority and the toxic antics of a House speaker named Newt Gingrich, while the economy — and Clinton’s approval scores — improved. By the time Bob Dole, who suffered an embarrassing series of early primary season defeats (including to Pat Buchanan in New Hampshire), finally secured the GOP nomination he was running far behind Clinton. And despite predictions throughout the spring of ’96 that the race would ultimately tighten, it never really did. After his defeat, Dole was known to lament that the election had come two years too late. Obama’s recent gains are tenuous, but it seems a lot more likely now than it did a few months ago that the 2012 Republican nominee will end up saying the same thing.