Matt Jackson
Matt Jackson appeared on Jeopardy! when he was only 23 years old and working as a paralegal in Washington D.C. The endearingly awkward Jackson won a total of $511,612 and became a fan favorite who was known for his catchphrases while finding the Daily Double clues. One of these catchphrases that he coined was “Boom!” after answering the Daily Double clues correctly.
Roger Craig
Roger Craig, a computer scientist and biochemist, competed on Jeopardy! in 2010 and amassed $503,200 in total winnings. He held the record for highest single-day winnings from 2010 until James Holzhauer broke his record in 2019. He also participated in the Tournament of Champions in 2011, taking first place and returned in 2014 for the Battle of the Decades.