This paper critically reviews the professional impact and functionality of the pervasive digital “matter” we have come to believe we can no longer do without. On the basis of a playful exploration of the first “half-century” of our digital age, an attempt is made to draw new perspectives for the next “level” of our digital culture in a broader (multi)media perspective and more specifically: the domains of Architecture. To stimulate an open-minded “second-half” debate, the paper puts forward some potentially promising (and hopefully provocative) conceptions and strategies for imaginative interface applications and game-based architectural study initiatives. Furthermore, the paper proposes the establishment of a new cultural platform for the exchange of Critical Digital hypotheses and the evolvement of visionary design concepts through creative digital innovation, with the (inter)active involvement of older and younger team-players