Since this episode was produced before the previous two that aired, Tobias (David Cross) is shown back in the prison doing his character study, despite being shown out of prison and sneaking around in the previous two episodes.
"Dorothy" and "Friend of Dorothy" are euphemisms for a homosexual.
David Cross had publicly mocked James Lipton (Warden Gentles) as part of his stand-up act, referring to Lipton as "pretentious" and "the most pompous, arrogant failure in history." Lipton was not amused by Cross' impersonations of himself, but during filming, they ended up becoming friends (although Cross maintained his criticism of Lipton's show, Inside the Actors Studio (1994)).
This was originally intended to be episode 16, instead of episode 1.16, Altar Egos (2004), which aired the week before it. This is because in this episode Tobias (David Cross) is still practising for his role as "Frightened Inmate #2," and there are no references to Gob (Will Arnett)'s wife (Amy Poehler), or Maggie Lizer (Julia Louis-Dreyfus).