Small began acting in the 1980s, having a recurring role in the sitcom Greentown as Kyle Saccania, a senior at Greentown High School who always disobeyed Coach Robert Gulch's (Anthony Broward) orders. Small became a household name during the Greentown era, and he developed friendships with his co-stars. In a 1986 interview, when asked if he was anything like his character on the show, he replied, "Kyle is the opposite of me. He is a troublemaker who sets out to rebel against authority. I'm a law-abiding citizen, and I was a good kid in school. I'm just glad I didn't have to use profanity."
Small made his film debut in the 1990s, in the film Coach Monday, in which he played defensive coordinator George Hapers and starred alongside Benjo Weaver. He was known as a "transition actor" by many after this role, because he went from playing a trouble-making student who rebelled against authority to playing an authority figure. Small, who was never a major fan of football, hesitated when asked if he wanted the role, and he finally agreed to take the role. His performance as Coach Hapers was "what every performance in a film should be", according to director Travis MacHammond.