President William Jefferson Clinton gives his Second Inaugural Address, the first Democratic president to do so since FDR sixty years prior at the first January 20th inauguration of a president in 1937.
President William Jefferson Clinton's reelection in 1996, the first time I was eligible to vote, was the first time a Democratic president to be reelected since Franklin Roosevelt in 1936, and again in 1940, and again in 1944. Before Roosevelt 32, the last Democratic president to win reelection was Woodrow Wilson, but Wilson never achieved over 50% of the popular vote unlike FDR. Clinton's 1992 and 1996 elections are similar to Wilson's 1912 and 1916 elections in that they both were Democrats to win election and reelection with just a plurality of the popular vote. At that point in 1916, Wilson was the first Democrat reelected, consecutively, since Andrew Jackson's reelection in 1832. Grover Cleveland won the popular vote three elections in a row in 1884, 1888, and 1892, but only the Electoral College in '84 and '92, so in 1912 Wilson was the first Democrat reelected since Cleveland. When FDR passed away just months into his fourth term in 1945, his third vice president, Harry S. Truman became the president. In 1948 Truman won reelection to the presidency in a contest everyone thought his opponent had won. While President Truman is a Democratic president that won reelection, it was also his first and only election at the top of the ticket. President Truman could've ran again at the top of the ticket in 1952 since he was unaffected by the 22nd Amendment, which limited presidents to two terms, but chose against running.
The next Democrat would be John F. Kennedy and he never had the chance to face the voters a second time. His Vice President Lyndon Johnson would succeed Kennedy and follow in Truman's (and Coolidge and Roosevelt 26) footsteps. LBJ would win his own election in 1964, a landslide, but all that would be lost four years later. Johnson 36 would realize he'd face challenges from within his own party when he lost the New Hampshire Primary to Eugene McCarthy in 1968.
Hubert Humphrey in 1968 came pretty close to being the next POTUS and in 1972 George McGovern had the opposite experience on his failed attempt at being the next Democratic president. In 1976, in another close election but with 50% of the popular vote, Jimmy Carter won the presidency. In 1980 he had the chance to be the first Democrat to be reelected since FDR. But it wasn't to be Carter. He'd be defeated by former California Governor Ronald Reagan. Carter would be the first incumbent Democratic president to lose reelection since Cleveland's first reelection bid in 1888, however as mentioned above, Cleveland won the popular vote just lost the necessary Electoral College majority AND Cleveland came back four years later and won reelection, non-consecutively. Before Cleveland 22's loss (and win) in 1888, the last incumbent Democratic president to lose reelection was Martin Van Buren. Franklin Pierce, James Buchanan, and Andrew Johnson were never given a chance by the party to face the voters at the top of the ticket. James K. Polk limited himself to one term. In 1848, MVB would try another run at the top of a ticket but lose his non-consecutive run as the Free Soil Party's candidate.
Clinton would hold the title as the first Democrat since FDR to win reelection and the first since Wilson since a Democrat won the presidency twice but with a plurality both times. Interestingly, so did Cleveland. President Clinton's eventual Democratic successor 8 years later will hold a new first for a Democrat since...well that's for another time.