Prison Blues is the fourth episode of the fourth season and 71st overall.
Whosie boisie hohhWill 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.
After their visit at the prison, Grace comforts Karen 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 and she overstays 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".
- Eric McCormack (Will Truman)
- Debra Messing (Grace Adler)
- Sean Hayes (Jack McFarland)
- Megan Mullally (Karen Walker)
- Shelley Morrison (Rosario Salazar)
- Eileen Brennan (Zandra)
- James Black (Anthony Dukane)
- Margaret Scarborough (Summers)
- Brent Sexton (Guard)
- Zandra's first appearance.
- While visiting Stan in prison, Will does an impression of Hannibal Lecter from the film The Silence of the Lambs (1991), which terrifies Grace.
- 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.
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. — Karen, asking Grace to leave
|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|
|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|
|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.|