The song "Smokestack Lightnin'" was not written or originally performed by the Grateful Dead. It is a blues song written and recorded by Howlin' Wolf in 1956. The Grateful Dead, like many other rock bands, often performed cover versions of songs they admired, and "Smokestack Lightnin'" was one of them. The lyrics of the song describe a feeling of longing and sadness. The references to "smokestack lightnin'" and the train symbolize the hardships of life and the despair the singer is experiencing. The smokestack lightnin' represents industry and hard labor, while the train represents escape and freedom. The lines "Why can't you hear me cryin'?" and "Let a hobo ride" convey the singer's desperation for someone to notice their pain and allow them a chance at a better life. The repeated plea to let a poor boy ride implies a desire for a better, less impoverished existence. The lyrics also hint at a love lost, with the line "Fare you well, I never see you no more." The singer is lamenting the end of a relationship and struggling to move on. Overall, the song captures the deep emotions of heartbreak, poverty, and yearning for a better life. The Grateful Dead's rendition of "Smokestack Lightnin'" helped introduce the blues classic to a wider audience and showcased their appreciation for the genre.