- One episode had Richard being commissioned to paint a nude portrait of a gorgeous woman. During their first session:Woman: I'm sorry, was I holding my arms like this or like this?Richard: Doesn't matter. I'm painting the bowl of fruit.Woman: Then why am I sitting here with no clothes?Richard: [beat] The shadow.
- "Caroline and the Cat Dancer" has Annie getting audited by the IRS. Once one gets past the initial "When did Niles Crane leave psychiatry to work for the IRS??" reaction, the scene is pure hilarity:[Annie is sitting nervously in IRS auditor Jimmy's office; he bangs the door open, thumps his sport coat on top of his computer monitor, then slams his briefcase onto his desk before turning to look at an even more terrified Annie]
Jimmy: It's not you.
Annie: ... good...
Jimmy: Need aspirin. [opens his desk drawer, takes out a bottle, and empties out two pills from it, which he then puts in his mouth] Oh. Okay. That's funny. Tic-tacs in the aspirin bottle again! [opens another drawer and spits out the mints, then yells toward his door] I HATE you people!
Annie: [getting up] You know, maybe I should come back tomorrow, you look like you're having a bad-
Jimmy: Life? Tell me about it! I just got passed over for the office with a window because I'm "too lenient".
Annie: Lenient is good! Jesus was lenient!
Jimmy: If Jesus worked here, He wouldn't have a window either, siddown. [she does; he opens her folder] You must be Ms. Spadaro, Case 2473.
Annie: Well, my friends call me "2-4". [chuckles]
Jimmy: [utterly unamused] I must meet your friends, they sound like a hoot. [Annie's smile disappears] Let's begin. [goes down the first page, making occasional marks] Good!... good!... good!
Annie: [brightening] Well, I did it right!
Jimmy: No, you did it horribly, I'll show them "lenient"! [hammers the page with a rubber stamp, then moves on to the next page; Annie looks more worried than ever as Jimmy begins marking the next page] Ha! Caught ya... caught ya again... [holds up the page] Is that a 9 or a 4?
Annie: [guessing] A 9?
Jimmy: [grinning] Caught ya again. [Annie buries her face in her hands]
Annie: Look, I've never been audited before, is there any chance I could go to jail for this?
Jimmy: [making more notes on Annie's tax return] If I want a window, there is. Okay! Need to see your receipts.
Annie: [handing over a shoebox labelled "1993"] Okay! Uh, receipts, I have them.
Jimmy: [opens the box and removes the receipts inside, which number...] Two.
Annie: [pointing] Actually, that one's for the shoes.
Jimmy: [drops the shoe receipt back in the box and replaces the lid] Are you really this incompetent or are you just doing this to cheer me up?
Funny / Caroline in the City