Pinchot was raised in southern California but after graduating from South Pasadena High School found his way back East to attend Yale University by way of a scholarship. He began college studying painting but became interested in acting.
Although he starred in several movies (including Risky Business, Beverly Hills Cop (1 & 3), It's My Party, and True Romance), he is perhaps best known for his role in the ABC family sitcom Perfect Strangers (1986 - 1993) as Balki Bartokomous from the (fictional) island of Mypos. Pinchot was nominated for an Emmy Award for Outstanding Lead Actor in a Comedy Series in 1987 for this role.
Pinchot guest-starred in a first-season (1996) episode of the NBC sitcom 3rd Rock from the Sun, playing the younger brother of Dr. Mary Albright (Jane Curtin).
From March 12 to August 15, 2004, Pinchot performed in the revival of Sly Fox on Broadway, opposite Richard Dreyfuss, Eric Stoltz, René Auberjonois, Peter Scolari, et al.
In March, it was announced that he would join Jose Canseco, Omarosa Manigault-Stallworth, Janice Dickinson, Carey Hart, Caprice Bourret, and Pepa on the fifth season of the VH1 series The Surreal Life, which premiered July 2005.