There have been studies made on a small scope comparing English Romanticism of the late 18th and early 19th century with the “romantic” qualities of the Japanese poetic revolution of the late 17th century. What Bashó and his followers did to haikai has some similarities with the transformation wrought upon Enlightenment literature by the Romantics. This work looks deeply at that comparison, hoping to use each movement to illuminate the other. One interesting phenomenon that the book explores is that somehow the Japanese were able to retain the humor of haikai, even while spiritualizing it with sabi, while English Romanticism lost the wit of the Enlightenment (before the “anti-Romanticism” of Byron), their earnestness becoming a wasteland in terms of humor. Why Japanese “romanticism” could use humor for transcendence and the English not? Answering that question illuminates not only the two literary movements, but the two societies.