Guest Stars Kristen Johnston as May-May Montgomery Steve Zahn as Peter Montgomery Emma Shannon as Young Judy J. Gaven Wilde as Young Jesse Tristan Borders as Young Kelvin Sean Whalen as Walker Keely Marshall as Young Amber Co Starring Jeff Campanella as Jon Carly William Ryan Watson as Protester #2 Lucy Catherine Haskill as Protester #1 Braxton Alexander as Trent Kathy McGraw as Waitress Ian Winningkoff as Young Chuck Montgomery Andrew Tickle as Distinct Man Michael H. Bishop as Young Karl Montgomery