Matthew Perry's best experience of his life took place in Chicago. In 1986, he was a relatively unknown TV supporting actor when he got his first film role in "A Night in the Life of Jimmy Reardon," directed by William Richert. The film, set in 1960s Chicago, starred River Phoenix as the lead character and Perry as his best friend. Perry expressed his immense excitement in his memoir, stating that he had never been so thrilled in his life. It was during this movie in Chicago that he fell deeply in love with acting. The cherry on top was that he and River Phoenix became close friends during their time together. They would often hang out, drink beer, and play pool on North Rush Street. Unfortunately, the film was released in 1988 and did not perform well. Tragically, River Phoenix passed away due to an overdose five years later, leaving Perry devastated. However, the memories of filming in Chicago remained happy for Perry. As the last day of shooting approached, Perry couldn't contain his emotions. He sat on his bed in his room at the Tremont Hotel and cried. He knew that he would never have an experience like that again—his first movie, being far from home, and being able to flirt, drink, and spend time with a brilliant young man like River Phoenix.