Reflecting on the question of media, this paper attempts to bridge the gap between attention and distraction in Bernard Stiegler and Walter Benjamin's respective philosophies. Based on Stiegler's philosophical theory, this paper will demonstrate, on the one hand, how harmful the destruction of attention, i.e. deficit hyperactivity disorder (Mattew, 2012), can be to intergenerational relationships which is constructed of retentions including tertiary retention, and the other hand, how Stiegler's theory is too exclusively focused upon 'Generation M,' that is children with hyper attention. We shall also analyze Benjamin's arguments regarding distraction, a state he never condemns because he finds new political possibilities there. Based on them, this paper focuses on German educator's arguments on film in 1910s-1920s and Azuma's arguments regarding Otaku. German educators find distraction and deep attention in film for education. This coexistence of distraction and deep attention in film has the political potential to overcome aestheticization of politics by totalitarian Fascist regimes. As Lee argued, attention gives children unexpected creativity for teachers (Lee, 2018). On the other hand, Azuma analyzes Otaku's work as a new type of subjectivity through the consideration of new media, Nico Nico douga. For Azuma, Otaku is inescapably linked to media such as anime, video games, and social media. From this perspective, he describes how blind identification with deep attention is destroyed by a mixture of commentators on the screen and comments that criticize the commentators. In Nico Nico douga, distraction is not disorder but self-reflection.