Guest Stars Josh Stewart as The Watcher / Will / Joshua Jason Antoon as Mr. Litchfield Luke Kleintank as Chris Minor Katelyn Tarver as Natalie Poston Anthony Michael Hall as Roy Minor Co Starring Andres Perez-Molina as Cop / Officer Shelley Robertson as Ruby Woods Roy Abramsohn as Doctor John Autry II as Jasper Woods Uncredited Mario Perez as John Cantone