Guest Stars Liam James as Young Shawn Kurt Fuller as Dr. Woodrow Juniper "Woody" Strode Becky O'Donohue as Molly Gogolack Charles Martin Smith as Roy Kessler Freddie Prinze, Jr. as Dennis Gogolack Adam Greydon Reid as Toby Shore Co Starring Carlos McCullers, II as Young Gus James Tyce as Thug #1 Kelly Metzger as Nerdy Woman Kate Gajdosik as Reporter Peter Yunker as Tim Bunting David Gore as Young Dennis