How do you define the underclass? The poor, those making under 50,000 or what I seen a whole lot on this site, the uneducated, those with a high school education or less? If you're talking about those making less than 50,000, the Democrats have won this group every year since 1992. That was the first year this stat was kept.
If you're talking about what has been called the uneducated, a High School or less education, Reagan won them twice and G.H.W. Bush once. Bill Clinton won them twice as did G.W. Bush. Obama won them twice and Trump won them once. Education is a mixed bag. I would say the candidate with the most charisma won this group.
FYI, on the other side of the coin, college grads went for Reagan twice, G.H.W. Bush, twice, Dole once, G.W. Bush twice, Obama, once, Romney and finally Hillary Clinton. The reason I decided to add college grads, the supposed educated class is I seen posters blaming Trump's victory on the uneducated or HS or less voting block. The educated vote Democratic. Not so. If only college grads decided whom would be president we would have had Reagan twice, G.H.W. Bush twice, he won college grads over Bill Clinton as did Dole who would have become president in 1996. G.W. Bush won them twice over Gore and Kerry, although Obama won them over McCain, but Romney would have become president in 2012 if college grads decided the presidential outcome. Of course Hillary in 2016. A mixed bag there.