This chapter provides insight into the new generation in Brazil who released their first feature films in the early years of the twenty-first century. It provides some context on Brazil's new movement of Garage Cinema which struck out in a new direction away from the Cinema da Retomada which characterized the second half of the 1990s, and sought to create a new digitally-inspired dramaturgy based on reduced production costs, alternative distribution outlets and a collectivist agenda. The chapter then moves on to a discussion of the failure experienced by some of the members of the Garage Cinema Generation on their journey towards success before turning to an analysis of the role played by the leitmotif of failure in the film Estrada para Ythaca/Road to Ythaca, directed by Luiz and Ricardo Pretti, Pedro Diógenes and Guto Parente, which won the Prize for Best Film at the Tiradentes Festival in 2010. In its Beckettian journey towards nowhere, and its allusion to ideas and events which are never made explicit (such as the mourning for an unnamed dead friend), Estrada para Ythaca is able to express the mood of the generation—enacting a drama which is elusive, unnameable and only present outside the space of the film, as encapsulated by Samuel Beckett's words in Westward ho: “Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”