Holmes Joining Sandlers Jack and Jill August 25, 2010 Katie Holmes Joining Sandler’s Jack and Jill? Katie Holmes is in talks to join Adam Sandler and Al Pacino in Jack and Jill. Scripted by Dennis Dugan, the movie follows a family man by the name of Jack deals with his twin sister, Jill, when she visits for Thanksgiving then won’t leave. Sandler will play both characters. Holmes is up for the role of Sandler’s wife while Pacino is set to play himself. Filming is expected to begin this October.