A poster for this video game is displayed in the window of Stars Hollow Video – the store obviously hires out games as well as movies.
Grand Theft Auto III is a 2001 action-adventure game developed by Rockstar. Set in fictional Liberty City (loosely based on New York City), it follows the adventures of Claude, who becomes embroiled in a world of crime, drugs, gangs, and corruption. The game received critical acclaim, was the best-selling game of 2001, was named Game of the Year, and is considered to be one of the greatest video games ever. It was also controversial for its depiction of sex and violence.
It’s possible that this is a foreshadowing of Rory’s own Grand Theft Yacht, but more likely a comment on freedom of speech.