Prison Blues is the 4th episode of the fourth season and 75th overall.

Will faces his fear of talking in front of a camera with the help of Jack's acting coach. Grace stays at Karen's mansion to comfort her while Stan is in jail.


Whosie boisie hohh

Ep 04 04-0

This is a very big opportunity.

Will freezes up in front of a camera while being interviewed about Stanley's case. All he could do is fumble on words and sigh "whosie boisie hohh".

Back at the apartment, the interviewer calls him again for another meeting and Jack answers saying that he will against Will's protests. Jack invites him to try an on-camera acting class taught by Zandra.

During the class, Will is dragged into the stage by Zandra to apologize "to someone you've wronged". Will, in an emotional breakthrough, apologizes to himself saying how much pressured he had put on himself and set himself up for failure. Will does the interview again in his new found confidence.

Grace's sleepover

Ep 04 04-1

"I'm his bitch, okay?!"

After their visit at the prison, Grace notices Karen is still distraught. She tries to comfort her by staying the night at her mansion. She wakes up feeling relaxed and after a little persuasion from soft-core porn, she stays another day. Things get out of hand when Grace overstays the visit and as Karen puts it, "is turning into one of those mean, abusive rich people".

Karen and Rosario send her back home by pushing her down the stairs out of the mansion. When she settles back in her apartment with Will, she sighs "This place is a dump".




  • Eileen Brennan (Zandra)
  • James Black (Anthony Dukane)
  • Margaret Scarborough (Summers)
  • Brent Sexton (Guard)


  • Zandra's first appearance.

Cultural references

  • Jack says he has watched the documentary Scared Straight! 17 times but it "never took". The film is about juvenile delinquents being bullied by actual inmates to "scare them straight" and avoid prison life.
  • While visiting Stan in prison, Will does an impression of Hannibal Lecter from the film The Silence of the Lambs (1991), which terrifies Grace.



Everybody ready to go on a little day trip? I brought my fanny pack, which I will hold as a clutch, so as not to obscure... my dynamite fanny. Jack

Grace:What I'm wearing isn't too revealing, is it? The men are locked up. I don't want to drive them into a state of sexual frenzy.
Guard:I wouldn't worry about it.
Grace:Oh, like you're so hot?
Entering the prison
Will:I haven't done a lot of acting before. Actually, that's not true. For 19 years, I played the role of a heterosexual.
Zandra:My guess is, not very convincingly.

Honey, if you want to leave, I know you've got things to do. I mean, there's fashion mistakes to be made, and it's probably happy hour at some gay bar. Karenasking Grace to leave

Rosario:She should be punched in the neck.
Karen:Hey, hey, hey, hey, hey. That's not very lady-like.
Rosario:With an open fist.
Karen:There's my girl.
dealing with Grace

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