Guest Stars Ora Jones as Claire Garland Bryan Greenberg as Howard Denton Kelli Simpkins as Dana Worth Torrey Hanson as Jack Ziegler Keith Kupferer as Mallory "Uncle Mal" Corcoran Kevin Gudahl as Judge Wainright Jasmine Batchelor as Maxine David Darlow as Theo Mountain Keith Powers as Lionel "Nasty Nel" Eldridge Dan Waller as Agent McDermott Gregory Linington as Mark Hadley Kroydell Galima as Greg Haramoto Elizabeth Ledo as Lynda Amir Henderson as Young Talcott Avery Holliday as Abigail Garland Phillip Edward Van Lear as Oliver's Doctor William Dick as Chief Justice Stephen Roosevelt Co Starring Dyllan Yelverton as Bentley Raluca Lazarut as Szuza Cheryl Hamada as Judge Reardon Diana Coates as Stephanie Pitts Phillip Cusic as Young Addison Edward Neequaye as Mason Tara Mallen as Yvonne Millie Hurley as Property Manager Michele Alvarez as Becca Reyes