After graduating from University of Windsor with a BFA, Cimolino began his career as an actor at Stratford in 1988.
During the Monette years, Cimolino established funds to provide financial stability for the Festival, and helped secure funding to open the Festival's Studio Theatre in 2002.
An accomplished director, Cimolino has staged successful Shakespearean productions in Stratford and Detroit.
[3] He is married to actress Brigit Wilson and has two children, Gabriel and Sophia.
In December 2015, Cimolino was appointed as a Member of the Order of Canada for contributions to Canadian theatre and arts leadership.