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 Mark Gibbon as The Fixer / Karl Kurz Adrian Hough as Mayor Jack Fife Aubrey Arnason as Dr. Lucy Fife Malcolm Sparrow-Crawford as Young Sam Gillis Laiken Laverock as Young Kim Collins Kyra Zagorsky as Gina DeLuca William Belleau as Hank Gillis James Pizzinato as Ezekiel Miller Jason Cermak as Arthur Conway Megan Leitch as Molly Shaughnessy Redden as Lawyer #1 Brady Droulis as Tommy Fife Darren Dolynski as Interviewer