Guest Stars Reed Birney as Sylvester "Pop Pop" Lisko Mila Morgan as Ginny Lisko Michael Greyeyes as Sam Gillis Scott Lawrence as Junior Johnson David Cubitt as Grant Williams Derek Richardson as Adult Richie Co Starring Dean Petriw as Young Matt Nicholas Holmes as Young Frank Kiefer O'Reilly as Young Richie Fife Adrian Hough as Mayor Jack Fife Mark Gibbon as The Fixer / Karl Kurz Aubrey Arnason as Dr. Lucy Fife Malcolm Sparrow-Crawford as Young Sam Gillis Laiken Laverock as Young Kim Collins Kyra Zagorsky as Gina DeLuca Jason Cermak as Arthur Conway James Pizzinato as Ezekiel Miller William Belleau as Hank Gillis Megan Leitch as Molly Shaughnessy Redden as Lawyer #1 Brady Droulis as Tommy Fife Darren Dolynski as Interviewer