And you won't believe how much the check was written out for!

A six-time Emmy Award winner, Jeopardy! host Alex Trebek has been a longtime and beloved fixture in American pop culture since the game show’s pilot episode aired in 1984. But success wasn’t always a sure thing for Trebek—or these 10 people who made the most money on Jeopardy!.

Trebek bounced around the broadcasting circuit for years trying to find steady work before he landed Jeopardy!, and it wasn’t quite the straightforward, linear arrival you’d imagine. Starting out on the Canadian airwaves, Trebek transitioned from the radio career of his early days to Canadian sports broadcasting to the American game show circuit. There, he took several gigs throughout the ’70s like High Rollers, Double Dare, and The $128,000 Question, but none of them really took, including Pitfall, a game show produced in Canada that showcased contestants attempting to cross an eight section bridge in 100 seconds by answering questions, avoiding “pitfalls” along the way. The show’s title should have been a harbinger for Trebek, as Pitfall’s packager, Catalena Productions, went bankrupt in 1982 just a year after he was hired. A $49,200 check that Catalena Productions wrote Trebek bounced. To this day, he hasn’t seen a dime.

“It came at a bad time because my father had died and I was in bad, bad straits and could have used the money,” said Trebek in David Baber’s Television Game Show Hosts: Biographies of 32 Stars. “Interestingly, in a career that spans 45 years, the only time I’ve been done that way was by fellow Canadians. Fellow Canadians shafted me.”

Just two years later, Trebek began hosting another fledgling trivia game show: Jeopardy!. In its second season, the show was paired with Wheel of Fortune (which Trebek also spent a brief period hosting in 1980 when Chuck Woolery fell ill for a week) and aired during a more desirable time slot. With the proper grooming, Jeopardy! bloomed into the colossal hit we all know today, and only a year after airing became the second most-watched syndicated series in the country. Here are 13 of Alex Trebek’s most memorable moments from Jeopardy!.

The $49,200 check from Pitfall still hangs in Trebek’s home, framed. If you’ve ever thought about trying out, see if you can answer these Final Jeopardy! questions everyone gets wrong.