The comic archetype of the Little Man--a nobody who stands up to unfairness--is central to the films of Woody Allen and Charlie Chaplin. Portraying the alienation of life in an indifferent world with a mix of pathos, irony and slapstick, both adopted absurdist personas--Chaplin's bumbling yet clever Tramp with his shabby clothes, and Allen's fool with his metaphysical witticisms and proclivity to fall in love too quickly. Both men were auteurs who managed to retain creative control of their work and achieve worldwide popularity. Both suffered from scandals regarding their attraction to younger women. Drawing on psychoanalysis and gender studies, this book explores their films as barometers of their respective historical moments, marking cultural shifts from modernism to postmodernism.