There’s two later season episodes I enjoy:
1.) Fanilow- Will waits in line for Barry Manilow tickets with fellow Fanilow Sara Gilbert. I love this exchange between Karen and Sara’s character:
KAREN: So you and Barry are lovers?
CHERYL: God, no. I wish! I've never even met him. But he has brought me to climax more times than any other man.
2.) One Gay at a Time-Grace joins AA for free therapy and pastries, featuring Molly Shannon as Will and Grace’s lunatic neighbor Val. I love this scene at the AA meeting:
KAREN: Attention, weaklings! This woman is a fraud. She's not an alcoholic.
VAL: Of course she is. If that's not a booze face, I don't know what is.
GRACE: [QUIETLY] Karen, get out of here.
KAREN: Grace, I am trying to help you. The first step is admitting that you don't have a problem. Come on, Grace, let's go.
VAL: She's staying! She's a horrible, horrible drunk.
KAREN: The only thing that's horrible about Grace is her hair and her clothes.
VAL: I know, it's like there no safe place to rest your eyes. She's staying!
KAREN: [WHILE PULLING GRACE OUT OF HER CHAIR] She's going!
VAL: [WHILE PULLING GRACE BACK INTO HER CHAIR] She is staying!
KAREN: [PULLING GRACE] She is going!
VAL: [PULLING GRACE] She is staying!
KAREN: [PULLING GRACE] She is going!
VAL: Accept the things you cannot change, bitch!
[KAREN PULLS A CORKSCREW OUT OF HER PURSE AND HOLDS IT UP TO VAL.]
KAREN: Time to pay the corkage fee, crazy.