- In "No Roll", when Debra and Ray are playing Sensuopoly, one of the squares instructs Ray to tell something about himself that Debra doesn't know. Ray's response? "I'm back from war!" (lunges at Debra)
- In "The Breakup Tape", Ray wonders just what presents Debra's past boyfriends had given her over the years.
Ray: "Is there anything in here [the bedroom] I should know about?!"
Debra: "...The picture frame."
Ray: "....THAT'S AROUND A PICTURE OF OUR CHILDREN! (Beat) Waaaaaaaaaait..."
Debra: "They're our kids, Ray!"
- Another such present was a poem entitled "Debra's Eyes". When, the next morning, Ray takes it upon himself to get some "new, better things" (i.e. replacements for all of the gifts), he also takes his own stab at romantic poetry:
One on each side, like a dainty cup
So gently they hold thine sunglasses up.
So round and nice, with a subtle ridge
There's no bone in there, it's cartilage."
- Many moments from "Older Women", the episode where Debra's divorced father arrives at Thanksgiving with his new girlfriend, who turns out to be a lot older than him. Most of them from Frank, including this line:
"Kill is going to Debra you!"
- "Jealous Robert", when Ray realizes that Debra set up Gianni with Amy to get Robert jealous:
Debra: Let me tell you something. The fact that Robert got jealous only means he still has feelings for her.
Ray: You DID do it. And the genius part of it all was leaking it to my mother. Because you knew, oh, you knew that telling her was just like whispering it into Robert's ear. Unbelievable. You believe that, Ma? She played you. She played you like a fiddle! What do you think of that, mom? (Marie has her back to Ray, cooking; Ray has a concerned tone to his voice because she's not responding) ...Mom?
(Marie casually turns around)
Marie: Your eggs are ready, Raymond.
Ray: Oh my God! You're in on it! This is sick! Who else is in on it? Amy and Gianni in on the whole thing, too?
Marie: All I needed was Debra.
- Then at the end of the scene, when Ray reluctantly agrees not to tell Robert:
Ray: (to Debra) So you've made me an accomplice. Your soul is as black as night.
- One of the show's classic moments, in "Marie's Sculpture", after Marie finally realizes a sculpture she made resembles a certain part of the female anatomy.
Marie: ...Oh my God, I'm a lesbian.
- And then there's Frank. Who takes even longer to figure it out despite staring at it all episode. It finally takes someone pointing it out for him.
Janitor: If you ask me, it looks like a *whispers*
Frank: ...Holy crap!
- When Ray is trying to tell Debra what the sculpture looks like:
Ray: Isn't it a bit too...ladylike?
- In "Snow Day", a slightly drunk Ray is trying to convince Debra that she should consider herself better than his family, pointing out all their annoying habits. When he gets to Robert, he lists off some of his quirks, eventually arriving at, "He separates his 'Good&Plenties' into 'Goods' and 'Plenties'!" He pushes a reluctant Robert to explain which is which...
Robert: ...The pinks are the "Goods"... and the whites are the "Plenties". Because there's always more of them. And they're not as good. [beat] And then there's a third category of "irregulars".
Ray: [grinning] And they're called?
- Drunk!Raymond loudly calling Frank a "baboon's ass."
- Ray and Robert's cringe worthy dance moves take the cake. Debra and Amy aren't any better, but Frank and Marie are quite talented.
- In "Season's Greetings", as the family is sitting around and making fun of other families' Christmas letters:
Frank: (reading) "Is it Christmas already? With our trip to colonial Williamsburg, remodeling the living room, and Denny's successful run for city council, the months have just flown by!" City council of what city? Jackassville?
- From "The Kicker:"
Frank: Come on, Robert, tell it like you're not a gelding.
Frank: Luck is the residue of design!
Frank: Shut up.
Debra: Frank, that's a record for the school. You know it's not right to keep that, don't you?
Robert: Don't bother, Deb. His soul was removed to make room for more stomach.
Robert: *runs in with the radio* They're talking about Dad!
Caller: You wanna know what that guy is? I'll tell ya - he's a jackass!
Debra: *gasps* They are talking about him!
- When Frank says he'll give the ball back for ten thousand dollars:
Host: So, Dave on line one, what do you think?
Caller: I think this Frank deserves to be kicked sixty-eight yards!
Marie: Finally, a voice of reason!
- When Frank says on air that he is Ray's father, Ray screams in frustration and smashes the radio into Marie's cake.
- When the rest of the family is trying to get the ball back to Hofstra, Robert throws it across the street to Ray and accidentally throws it straight through a window. Ray stands there staring at it for a good twenty seconds with an "Are you freaking kidding me?" look on his face.
- This, solely for the image it puts in your head:
Marie: You can't print that! You don't attack your family in public!
Ray: What are you talking about?! You took a swing at him at the mall last week!
Marie: *dismissively* That's different, he was doing skits in the lingerie store.
- In "Call Me Mom", Debra enters Frank and Marie's kitchen, and Marie is in another room. Debra asks if she can see her, and Frank says, "Let me get her for ya. MA-RIE!!!!!"
Robert: She will be with you presently.
- From "Mother's Day", while Ray and Frank are arguing over who is right, Debra or Marie:
Frank: Well who the hell is Marie to come barging in demanding joy, while Debra's wrestling with the damn kids?
Ray: She didn't have to be so rude!
Frank: (Points at Marie) Rude is the only thing that gets through to her! How do you think I got the way I am? I USED TO BE A GENTLEMAN!!