Stevie Ray Vaughn was arguably the best blue guitarist of his age with the possible exception of Eric Clapton. Vaughn and his group Double Trouble had started the climb to fame when the Rolling Stones heard them in a Dallas club. By the summer of 1990 Vaughn and Double Trouble were touring the nation as A-liners along with Clapton and also The Robert Cray Band. Late on the evening of August 25, the groups had finished a performance at the Alpine Valley Music Theater in East Troy, Wisconsin, and were due to travel back to Chicago. The bands were supposed to take a bus back, but Vaughn had wrangled seats on the helicopters used by Clapton’s location crew for himself, his brother, and sister-in-law. However, of the three expected seats, there was instead just one seat, which Vaughn took in order to return sooner to his girlfriend in Chicago, Janna Lapidus. The rest of Double Trouble returned to Chicago on the bus; it was not until after they arrived in the Second City the next morning that they would learn of the disaster in the night skies over southern Wisconsin.
The Bell BHT-206B that was transporting Vaughn is from the same line of helicopters (the JetRanger) in which Disney chief Frank Wells was flying during his fatal air crash in 1994.