Ryan Reynolds appeared in Hillside (1990), a Nickelodeon series taped in Florida with many other Canadian actors. After the series ended, he returned to Vancouver where he played in a series of forgettable television movies. He did small roles in Glenn Close's Serving in Silence: The Margarethe Cammermeyer Story (1995) and CBS's update of In Cold Blood (1996). However, his run of luck had led him to decide to quit acting.

One night, he ran into fellow Vancouver actor and native Chris William Martin. Martin found Ryan rather despondent and told him to pack everything: they were going to head to Los Angeles, California. The two stayed in a cheap Los Angeles motel. On the first night of their stay, Reynolds' jeep was rolled downhill and stripped. For the next four months, Ryan drove it without doors. In 1997, he landed the role of Berg in Two Guys, a Girl and a Pizza Place (1998). Initially, the show was reviled by critics and seemed desperate for any type of ratings success. However, it was renewed for a second season but with a provision for a makeover by former Roseanne (1988) writer Kevin Abbott. The show became a minor success and has led to additional film roles for Ryan, most notably in the last-ever MGM film, a remake of The Amityville Horror (2005).