Lyric discussion by ToadSprocket 

Casey Jones was the one of the worlds most famous train engineers. He ran the CannonBall Route between Chicagp and Memphis. Way back in 1900, a fellow engineer called out sick. Casey took the route but now was nearly 1hr 45 minutes behind. As we all know, being late is not good in railroad life. So Casey, being the best there is, ran the route going at times over 100MPH and averaging close to 65MPH over a very dangerous curvey run. He was close to schedule at his 2nd to last stop and departed for the final leg. Unbeknown to him and his crew, another train heading towards him was having problems. Trains travel both ways on the tracks and the train headin South has precedence over the train heading North. The NorthBound train must go into an adjacent track while the other train passes. Unfortunately the other train (train hundred and two) didnt get off the main track so Casey's train whammed into it. Casey Jones died at the crash. He was never on cocaine during his last run - those lines were just added by the Dead.

Driving that train - refers to casey jones the famous conductor in 1900 high on cocaine - not true but it can refer to going fast like a cannonball casey jones you better watch your speed - he dude love to push the trains to their limit & he was the best there was lady in red - the caboose of the other train he smashed to pieces

@ToadSprocket This song is not about Casey Jones the train conductor. It's a metaphor for someone speeding out of control. That someone was one of the Merry Pranksters and their dear friend, Neil Cassady. He was typically driving their school bus named "Further" He was traveling in Mexico in the winter of 1968. He passed out by railroad tracks and died of exposure. Casey Jones is a song about Neil Cassady.

But don't believe me, read all about the Merry Pranksters and the Grateful Dead in the book, "The Electric Kool Aid Acid Test"

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