Comparisons between books and movies tend to instigate intense conversations. Adapting a film is no simple task, but contrasting the two products can also be an erratic process, regardless of how much one tries to gather all of their ideas together. A mere observation can bring about diverse opinions or daring suggestions on how readers / viewers would have portrayed a certain scene or a small but crucial detail. In the end, it comes down to the charm of taking on the active role of a “critic” and analyzing the choices that were made alongside possible alternatives. The respective article will talk about how the novel “Wonder Boys”, written by Michael Chabon, came to be interpreted in a different medium, as a comedy-drama film from 2000, directed by Curtis Hanson. “Wonder Boys” may be perceived as a world of freedom from various outlooks. In 1995, Chabon – already ahead of his time – produced a small universe in his novel, where his characters could express themselves candidly. In 2000, Hanson went from being a reader to an avid interpreter and creator of his own “Wonder Boys”. Up until today, fortunate people, who come across the book and the film, can spot the director’s ingenious approach, accompanied by his constant loyalty to the writer’s concepts. We are dealing with a piece of work which should be discussed more frequently in classrooms or university lectures, due to its representative teacher-student bonding, the twisted realistic world – in which troubled individuals can still become inspirations for others – and its quality to be replicated in such inventive ways.