In day 3, Goober is outside the medical clinic. After talking to him, you discover he claims to have been an actor and names four movies he was in. After unsuccessfully trying to talk to the nurse inside, you get the option of asking Goober to reenact one of this scenes for her. Pick a movie, head inside and watch him complete his scene (don't do anything else) and leave. Repeat for all four movies and the achievement will unlock.