A recurring theme in songs performed by the Grateful Dead was that of trains. It not only occurs in original Dead tunes but also in songs that they covered by other musicians. In all the Dead performed over three dozen songs about trains or with "train", "trains" or "railroad" in the lyrics.
Dead originals that feature trains are "Casey Jones", "Jack Straw", "Lazy River Road", "Might As Well", "New Speedway Boogie", "Tennessee Jed", "Terrapin Station", and "They Love Each Other" with lyrics by Robert Hunter "Unbroken Chain" by Bobby Peterson, and "Tons of Steel" by Brent Mydland.
Bob Dylan referred to trains in "It Takes a Lot to Laugh, It Takes a Train to Cry", "Stuck Inside of Mobile with the Memphis Blues Again", "Visions of Johanna", and "When I Paint My Masterpiece" which were all performed by the Dead. "Slow Train" was performed during the Dylan and the Dead tour.
Chuck Berry's "Promised Land", "Johnny B. Goode", and "Let It Rock" have trains in the lyrics as well as "Beat it on Down the Line" and "Monkey and the Engineer" by Jesse Fuller. Other popular songs performed by the Dead with trains are "Ballad of Casey Jones","Big Railroad Blues", "Dark Hollow", "Early Morning Rain", "Green Green Grass of Home","I Know You Rider", "Little Sadie", "Me and Bobby McGee", "Wabash Cannonball", and several other songs.
Why trains? I can't answer for any specific song writer but this is a recurring theme in old blues, country, and folk songs, especially in the early part of the 20th century. They were a common mode of transportaion for drifters and hobos. Trains were often how loved ones either left town or returned, which are subjects that are popular in songs.
Every town had a railroad station or at least a siding where the trains stopped. The railroad was the most advanced way to travel for the average person and the common man could easily identify with the people who operated the trains and travelled on them.
Big trains, those tons of steel belching smoke across the land, were a favorite subject of the old songwriters and the tradition was carried on by the Grateful Dead.
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