This essay examines the parable of the prodigal son in the New Testament and compares it to different visual and literary representations from the 1920s in Europe. The story of the prodigal son revolving around themes such as family, home, resistance, order and restoration will be juxtaposed with texts and art works from the so-called Lost Generation, a generation of artists and thinkers developing and rebuilding new art in a continent shattered by the atrocities of World War I. The essay examines the conflict between generations and worldviews that emerges in the 1920s and the prodigal artists’ reorientation in a fragmented world in which it is hard to feel at home.