Ken Jennings had the longest winning streak on Jeopardy. He won 74 games
In total, he earned $3,022,700 from the show ($2,520,700 from 74 wins, $2,000 second-place prize in his 75th game, and a $500,000 second-place prize in the Jeopardy! Ultimate Tournament of Champions)
In comparison, Aimee and Al didn't do so well...
(Sources: 1, 2)