Tillman went to John Marshall High School in Milwaukee and he took Mass Communications Magnet Classes. As a teenager, Tillman made amateur videos and created "Splice of Life", which was a program for a local Public-access television. After high school, Tillman attended Columbia College in Chicago and majored in Film and Video. Tillman decided to move to Chicago because he thought a lot was happening there creatively. "There is a lot of theater there, and there are a lot of things happening in Chicago that I wanted to be a part of, so that's where I went to film school," according to Tillman. While in film school, he created a 30-minute short, "Paula", which was a story of a 17-year-old, single African American mother who works in a diner and motivates the people around her. "Paula"'s success attributed to numerous awards including the Black Filmmaker's Hall of Fame Award "George Tillman Jr.". and winning the Midwest Regional, Dramatic Category, of the Academy of Motion Pictures Arts and Sciences' 19th Annual Student Academy Award competition (1992). In 1991, Tillman graduated from Columbia College and became a part of a directing and producing partnership with his fellow college, Robert Teitel, and together made their company, Menagerie Films. During that time, Tillman supported himself by being a production assistant. He helped work on various commercials, but he always knew he wanted to direct. "Usually, I was the first guy on the set and the last guy to leave—eighteen hours of hard work. And I just felt like if I want to direct, why am I doing this?" Tillman's only experience of being close to a director was made was when he worked on the film, "Mo' Money". The writer of "Mo' Money", Damon Wayans told the union that he wanted more African Americans to be a part of the crew, which is the major reason why Tillman got hired. Tillman was a set dresser and was able to see how they made the film. At that point, Tillman realized that if he wanted to direct he had to write his own script to make everything happen. "It was going to be a long road from being a PA (production's assistant) to a director."