This Monkees track, written by “Lewis & Clarke” (the writing credit taken by songwriting team Michael Martin Murphey and Owen Castleman), was selected and sung by Michael Nesmith, furthering the explorations of country and country-rock by which he’d be better known in his solo career. The song’s narrative point of view is not entirely clear and can be confusing. It’s about a young San Antonio man who takes a train down to Mexico—“Just a loudmouth Yankee I went down to Mexico,” it starts. In places the song has not aged well. The singer admits, for example, “I lightly took advantage of a girl who loved me so”—that “lightly” seems to be doing its share of heavy lifting here. Should I stay or should I go? is the question that plagues the siinger, and ultimately (apparently) becomes the source of his greatest regret. Or, or as he somehow movingly bewails it in the chorus, “What am I doing hangin’ ‘round? ... I should be ridin’ on that train to San Antone.” It’s my favorite part of the song and the place where I can most easily ignore the singer’s somewhat loutish behavior, because at that point he is full of regrets that can never be answered for. The question is a bit muddled—at first it seems to be about staying in Mexico too long, but later it seems to be about how long it took him to get back. By which point, sadly, it’s too late, baby, baby it’s too late. “Then she told me that she loved me not with words but with a kiss” is a moment that can never be recovered, seared into this song. That’s all. It feels like that and train whistles in the distance are going to haunt him for the rest of his life.
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