It Takes a Lot to Laugh It Takes a Train to Cry
Taj Mahal Lyrics

In Taj Mahal's cover of Bob Dylan's "It Takes a Lot to Laugh, It Takes a Train to Cry", the lyrics are a reflection of the singer's thoughts and observations while riding on a train. The first two lines, "Well, I ride on a mailtrain, baby, Can't buy a thrill", suggest the singer's dissatisfaction or boredom with his current situation. He then describes staying up all night and leaning on the windowsill, suggesting that he is lost in thought or perhaps contemplative. The following lines, "Well, if I die on top of the hill and if I don't make it, you know my baby will" suggest a sense of recklessness or perhaps a longing for adventure.

The second stanza focuses on the beauty of the natural world outside the train window. The moon shining through the trees, the brakeman flagging down the "Double E" (likely a reference to the famous train the Empire Express), and the sun setting over the sea. The final line, "Don't my gal look fine when she's comin' after me?" suggests that the singer is not alone on this journey and is perhaps traveling with a loved one.

The final stanza describes the onset of winter and the singer's desire for a meaningful connection with his lover. The line "I don't wanna be your boss" suggests that he desires a more equal partnership. The final line, "Don't say I never warned you when your train gets lost" could be interpreted as a warning to his lover that there may be challenges ahead and he will not take responsibility for her unhappiness.