In the 1990s, Unexpected Company was based in Sewanee, Tennessee, under Hillman's direction at St. Andrew's-Sewanee School and the University of the South.
In that era, over thirty different performers worked with the group, with alumni Joe Petrilla, John Stewart, and Michael Barker going on to successful careers with the Titanic Players at Northwestern University and ImprovOlympic in Chicago and Los Angeles.