Behind a high stonewall surrounding a rural farmhouse in Auvergne, Guy Debord, the ex‐Situationist theorist and activist, retreated. The grungy, cheap‐thrill Parisian urbanism of his youth was no more. Paris had died in his arms of a fatal illness that has seen off other great cities. Economic forces and planning initiatives had assassinated his rebel underworld, and culprits are still at large, still awaiting trial in the people’s court. This essay embraces Debord the other side of the wall, dialoging with Pierre Mac Orlan, one of his favorite novelists. In so doing, we enter the phantasmal zone of the sentimental city, the city both real and make‐believe, defunct and yet‐to‐be. Mac Orlan’s ideas about passive and active adventuring are explored here, to unlock the Pandora’s box of Debord’s urbanism. The essay approaches the capitalist city with a poetic gloss and reveals a realm richer and deeper than most social scientific urban research can grasp. Alongside Mac Orlan, Debord retraces his steps through urban ruins, and recaptures an everyday melancholy of backstreets and damaged people, of twilight nooks and crannies and shadowy bars. In Debord’s sentimental city, it isn’t so much the past that one regrets as the future.