The chapter will consider The Trip (2010) and Cruise of the Gods (2002) as movies in which travel is inextricably combined with being engaged in play or games. Both films feature professional actors as the main characters, for whom the consequences of mimicry and unfulfilled ambitions are especially important, as well as their fans, who tend to relive and revisit the stars’ famous roles. In both cases, the characters’ actions and thoughts are dictated by the desire to reach the seemingly inaccessible heights, which the actors they venerate represent. In case of The Trip, the classic and loved star actors in their iconic roles represent a goal which the protagonists strive for in their playful mimicry. At the same time, they remain pragmatic in their desire to achieve greatness on par with the great movie stars of old. The actors play fictionalized versions themselves, with certain traits exaggerated for comical effect, which makes it difficult to distinguish between reality and fiction. The second film shares a similar concern with fantasy invading reality. In Cruise of the Gods, the idols are the filmmakers because of their connection with the divine authority and greatness of the fictional characters and worlds in the fans’ most cherished series. In their oneiric attitude towards the game(s) they are collectively engaged in during the cruise, they want to forget that their favorite characters were played by actors and prefer to equate the performers with their roles. This causes resentment of the protagonist of the film, Andy Van Allen, who seeks to cut his ties from his old performance and does not understand the dynamics of relations between the star and the fandom.