In 1995 Robb directed a film called Don's Plum that starred, then up and coming actors Leonardo DiCaprio and Tobey Maguire. Supposedly DiCaprio and Maguire agreed to star in the film if the film was never released in the USA; Robb disputed this claim. When Robb met with distributors DiCaprio and Maguire sued. The two sides settled out of court, agreeing never to show the film in the USA or Canada.
Robb has over 20 acting credits, the last of which were voice acting work for the Jade Empire video game. Other credits include roles in Matilda and The Brady Bunch Movie. In 2017, he played a headshot Photographer in an episode of The Goldbergs, an episode which referred to his success as a child actor in A Christmas Story and his mother's job as an acting manager as central to the plot.
