Joe Connolly staged more than 70 wrecks and destroyed at least 146 locomotives between 1896 and 1932. He even earned the nickname “Head-On Joe.”

From 1896 until the 1930s, staged train wrecks were a popular—albeit destructive—event at fairs and festivals across the U.S., long before anyone ever thought of wrecking old automobiles at a demolition derby or monster truck rally.

For one event, Connolly went to the state fair board in Des Moines and offered to put on a crash for $5,000. 

That initial price was a bit too steep for the board but he came back with a more acceptable offer: $3,000 plus a cut of the ticket sales.

 The board agreed and on September 9, 1896 Connolly held his first staged wreck. 

About 5,000 people paid 50 cents each to sit in the grandstand to watch the show and thousands more stood along the fence outside. The wreck was a success and both Connolly and the fair made a profit.

https://www.atlasobscura.com/articles/staged-train-wrecks