In 1824, Andrew Jackson would win a plurality (yet not a majority) of both the popular & electoral vote, however thanks to a "corrupt bargain" by Henry Clay & John Quincy Adams, Jackson would still lose the election to become the 6th President. Jackson would defeat Adams in the next election however, denying HIM a second term & becoming the 7th, & first Democratic President.

In 1876, Rutherford Hayes would defeat Samuel Tilden by 1 Electoral vote in the election, despite Tilden winning a good chunk of the popular vote. Initially, the electoral college count was 184 for Tilden to 165 for Hayes (185 were needed to win), but a ton of shenanigans occured that gave those 20 needed votes to Hayes (in compensation for basically starting segregation in the South 😭).

In 1888, Grover Cleveland would lose his chance to win a second consecutive term to Benjamin Harrison, despite winning the popular vote, thus assuring the 22nd President wouldn't be getting two consecutive terms, & giving America it's 23rd President. This marks the only time someone lost the election while winning the popular vote in a bid for reelection, however, Cleveland would gain revenge on Harrison in 1892 when he won a second presidency to become the 24th President.

In 2000, famously, George W. Bush, son of George Bush, would defeat Vice President Al Gore by just 5 electoral votes despite losing the popular vote by 500,000 votes, all because of a legal recount in Florida, all for a bid to become the 43rd President.

In 2016, the first time a woman would win the popular vote, ex-First Lady Hillary Clinton would still lose the electoral vote to New York Businessman Donald Trump in a bid to become the 45th President (he would win again in 8 years to become the 47th President as well).

Jackson, Tilden, Cleveland, Gore, & Clinton are all Democrats.