Pathetic...
1892 Democrat ticket: Grover Cleveland/Adlai Stevenson WON
1896 Democrat ticket: William Bryan/Arthur Sewall(Thomas Watson) LOST
1900 Democrat ticket: William Bryan/Adlai Stevenson LOST
1908 Democrat ticket: William Bryan/John Kern LOST
1924 Democrat ticket: John Davis/Charles Bryan LOST
1952 Democrat ticket: Adlai Stevenson II/John Sparkman LOST
1956 Democrat ticket: Adlai Stevenson II/Estes Kefauver LOST
1992 Democrat ticket: William Clinton/Albert Gore Jr. WON
1996 Democrat ticket: William Clinton/Albert Gore Jr. WON
2000 Democrat ticket: Albert Gore Jr./Joseph Lieberman LOST
A bunch of perpetual candidates in this list. Charles Bryan was the brother of perpetual presidential loser William Jennings Bryan (who also lost his fight against Darwinism in the 1920s). Two of the perpetual candidates held the office of VP; Adlai never got the presidency although his namesake grandson did get the nomination. Adlai II's VP runing mate Estes Kefauver left fellow Tennessee senator Albert Gore Sr. in the dust (both tried to get the party nomination for president) thus passing the loser baton to another generation...
I've been familiar with these names for some time, but 2 websites helped in the fact checking/research for this post:
Atlas of United States Presidential Elections
Grolier's Encyclopedia of Presidents (They Would Be President)