"The Road Not Taken," perhaps the most famous example of Frost’s own claims to conscious irony and "the best example in all of American poetry of a wolf in sheep's clothing." Thompson documents the ironic impulse that produced the poem as Frost's "gently teasing" response to his good friend, Edward Thomas, who would in their walks together take Frost down one path and then regret not having taken a better direction. According to Thompson, Frost assumes the mask of his friend, taking his voice and his posture, including the un-Frostian sounding line, "I shall be telling this with a sigh," to poke fun at Thomas's vacillations; Frost ever after, according to Thompson, tried to bring audiences to the ironic point, warning one group, "You have to be careful of that one; it's a tricky poem - very tricky" (Letters xiv-xv). Thompson's critical evaluation is simply that Frost had, in that particular poem, "carried himself and his ironies too subtly," so that the poem is, in effect, a failure (Letters xv). Yet is it simply that - a too exact parody of a mediocre poetic voice, which becomes among the sentimental masses, ironically, one of the most popularly beloved of Frost's "wise" poems? This is the easiest way to come to terms critically with the popularity of "The Road Not Taken" but it is not, perhaps, the only or best way: in this critical case, the road less traveled may indeed be more productive.
For Frost by all accounts was genuinely fond of Thomas. He wrote his only elegy to Thomas and he gives him, in that poem, the highest praise of all from one who would, himself, hope to be a "good Greek": he elegizes Thomas as "First soldier, and then poet, and then both, / Who died a soldier-poet of your race." He recalls Thomas to Amy Lowell, saying "the closest I ever came in friendship to anyone in England or anywhere else in the world I think was with Edward Thomas" (Letters 220). Frost's protean ability to assume dramatic masks never elsewhere included such a friend as Thomas, whom he loved and admired, tellingly, more than "anyone in England or anywhere else in the world" (Letters 220). It might be argued that in becoming Thomas in "The Road Not Taken," Frost momentarily loses his defensive preoccupation with disguising lyric involvement to the extent that ironic weapons fail him. A rare instance in Frost's poetry in which there is a loved and reciprocal figure, the poem is divested of the need to keep the intended reader at bay. Here Frost is not writing about that contentiously erotic love which is predicated on the sexual battles between a man and a woman, but about a higher love, by the terms of the good Greek, between two men. As Plato says in the Symposium (181, b-c), "But the heavenly love springs from a goddess [Aphrodite] whose attributes have nothing of the female, but are altogether male, and who is also the elder of the two, and innocent of any hint of lewdness. And so those who are inspired by this other Love turn rather to the male, preferring the more vigorous and intellectual bent." If the poem is indeed informed by such love, it becomes the most consummate irony of all, as it shows, despite one level of Frost's intentions, how fraternal love can transmute swords to plowshares, how, indeed, two roads can look about the same, be traveled about the same, and be utterly transformed by the traveler. Frost sent this poem as a letter, as a communication in the most basic sense, to a man to whom he says, in "To E. T.," "I meant, you meant, that nothing should remain / Unsaid between us, brother . . . " When nothing is meant to remain unsaid, and when the poet's best hope is to see his friend "pleased once more with words of mine," all simple ironies are made complex. "The Road Not Taken," far from being merely a failure of ironic intent, may be seen as a touchstone for the complexities of analyzing Frost's ironic voices.