#1. Ken Jennings

Jeopardy!: $4,522,700

Are You Smarter than a 5th Grader?: $500,000

Grand Slam: $100,000

Who Wants to Be a Millionaire: $100,000

1 vs. 100: $714.29

Total winnings: $5,223,414

Jennings won $2,522,700 on a 75-episode run on Jeopardy!, winning the rest on return appearances.