- "Marie's Vision": "A loveless marriage!?!?" and the conversation that followed.
- In greater detail: Marie needs to get glasses due to some vision problems, and starts pointing out flaws in everyone's appearances. Ray, Debra, and Robert all take steps to address the criticisms (Ray dyes his hair, Debra puts on extra mascara, and Robert gets Botox), but Frank, as usual, ignores what Marie has to say. When Marie tells everyone that they don't have to change for her, she also takes the opportunity to tell Frank that at least they listened to her, unlike him. That's when she comments that their marriage is loveless...and that's when Frank absolutely explodes. It's one of the only times in the series that we see him completely and utterly furious—no jokes, no sarcasm. He grabs the glasses from Marie and snaps them in half with his bare hands, then storms out. Later, the conversation between the two reaffirms their love in a quiet way.
- Ray finds a dog, puts up posters. Robert says they couldn't get a dog when they were little because of Ray's "allergies". Ray says he's clear of the allergies, and gives the dog to Robert. Then the dog's owner shows up. Ray offers to lie to the owner, but Robert decides to do the honorable thing and gives the dog back. Too bad he's already had it neutered. Too bad it's a stud dog. Too bad the owner wants two thousand dollars for it. Too bad Ray writes the check after about half a second of consideration-wait, that's not too bad at all!
- That five minute interval in the final episode where Ray isn't waking up after surgery, especially Robert.
"Listen to me! I am his brother, I can wake him up! Raymond! My brother's in there! RAYMOND!"
- After Robert finds out an odd secret about his latest girlfriend that he was sure was "the one", he goes on a very quiet, very passive line of dialogue to his family: "I wish I had a good reason why I'm always striking out. But I don't. It's me. It's me. Most people find their other half. And I just have to wake up and accept already that maybe there is no other half... for this." The look on his face and the other Barone's pained expressions make it even sadder. Even worse, they then try to comfort him, even Frank, but Robert completely ignores them and just walks out without saying another word.
Frank: "Hey! Son!"
- Frank standing up from his chair and calling out to Robert just before he closes the door really shows the heaviness of the situation.
- "The Angry Family." When one of the kids writes a little picturebook about how angry his whole family is, the local pastor calls the family in to discuss it. When the school counselor merely asks where everyone thinks the anger in the household might come from, it quickly devolves into everyone screaming and blaming one another. Debra claims it's not her fault she's angry when she has to put up with Raymond's family, Frank blames the problem on Debra and Marie butting heads, Raymond is too spineless to speak up at all, Robert blames the whole dysfunction on Raymond's inordinate amount of attention, and Marie claims there's no problem at all and that over-coddling teachers and schools just make our children feel entitled and blame the mother if anything goes wrong (Immediately after attempting to pin the blame for all the anger on Debra). Just when everyone's had a rant about how they're the ones who get the short end of the stick in the family (and not caring about anyone else), the pastor speaks up.
"Well... Thank you, everybody, for a lovely morning. Believe it or not, I do understand the pressures and tensions of raising a family in today's world. But I think maybe this particular family compounds the problem by being too close to each other constantly, like ping-pong balls pounding and bouncing off one another in the lottery machine. Except nobody wins in this game. Least of all, the children. Which is what I got from this book. (Turns to each Barone in turn) So it's not about you. Or you. Or you. Or you. Or even Raymond, today. It's about this little guy. (Holds up the book) And his sweet, simple way of...maybe giving you a message."
- "Boys' Therapy": When it is revealed that Frank's own father was physically abusive to him growing up. Frank, for all his faults never was this to either Raymond OR Robert. He says the reason he never was with his boys is because he was always weaker than his father. One of the rare instances where you want to hug Frank.
- "The Breakup Tape" features a bit of a sad revelation into Ray's character. In the episode, Debra finds an old audio recording of a message that one of Ray's old girlfriends left for him 20 years ago, where she breaks up with him without offering a proper reason. Although there is a lot comedy played with at Ray's expense for keeping such an old recording, his eventual reasoning for it is a little sad. He reveals to Debra that he kept it because it left him confused. In his point of view, things seemed to be going well for him up until that time, so the breakup came as a shock in just how unwarranted it felt. The scene frames Ray as very insecure in this moment, and one can't help but feel empathetic for the guy that he's had to carry that baggage for so long.
- The episode itself won Ray Romano the Emmy for Outstanding Lead Actor in a Comedy Series, an immense rarity for stand up comics (given how Emmy voters tend to see them more as writers than actors). He was the first one since Roseanne to do so, and no one has done it since.
- The last couple minutes of "Grandpa Steals". Some background: Frank set a bad example for Ally by sampling at the grocery store when the sign said not to (then mocking the grocer who pointed it out). Ray, Debra, and Marie guilt-tripped Frank about his behavior, and after having a one-on-one talk with Ally to regain status in her eyes, he decided to go back to the store and apologize to the grocer. Unfortunately, the grocer didn't accept his apology and called him a jerk and a maniac. It's hard not to feel a little sorry for Frank at that point; while he was the bigger person, you hoped the two could have made peace, especially since apologizing is such a hard thing for Frank to do.
- Any of the countless moments that highlight Robert's status as the Unfavorite, such as this one:
Marie: And you, you're not up to their standards either.
Robert: I know. (Beat) What are we talking about?
- In "Lucky Suit", it seems like a typical meddlesome Marie scenario when she ruins Robert's lucky suit for his FBI interview then compounds it by sending over a long and embarrassing apology letter, then going to the offices in person to apologize further...until she confesses to the interviewer that she did all those things on purpose to sabotage him, because he was one year away from police force retirement and she was tired of worrying every night whether Robbie would come home safe. It's a very moving monologue that really nails the fear that every family member must have in some form for a loved one on the force.
Marie: He was supposed to retire!.... He's a year away from not being a police officer, which means I could stop worrying about him every second of the day. I want him to be safe. Now he wants to go from one dangerous job to another? How long do I have to walk around with a knot in my stomach? Forever? I can't do it anymore. It's too much.
- "Separation", where Debra's parents get divorced. Especially well-done is the scene when Warren consoles Debra.
Debra: I'm so sorry, Dad.
Warren: Yeah, me, too.
Debra: Sorry she's doing this to you.
Warren: What do you mean?
Debra: I know how she is.
Warren: Here, sit down. This is not your mother's fault.
Debra: Don't you defend her-
Warren: Listen to me. We have both been unhappy for some time now. You know that.
Debra: All right, but you're the one who at least tries to make an effort, like wanting to go to that marriage counseling.
Warren: Can I tell you something? I never really wanted to go to New Jersey. You want to know why I picked that place? Because I was looking forward to how much your Mother would hate it. Well, she loved it, and I was the one bored out of my freakin' skull. Those workshops, "Polishing your soul mate's soul." So you really mustn't blame your mother, honey. I'm the one who actually said it was over.
Debra: I don't believe it.
Warren: It's true.
Debra: And what did she say?
Warren: Well, she knew. We both knew. Don't cry, honey.
Debra: I can't help it. I mean, why the hell do you take vows if they don't mean anything?
Warren: We meant it then. We meant it when you were kids. But when your sister and then you went off to college, it kept getting harder.
Debra: Well, what about all the kissing, the traveling together and the POOKUMS 1 and 2 license plates? What was that?
Warren: I know. I know. I guess, by the end, most of that was just a show. And we had enough. We both had enough. [beat] It's not like Ray's parents.
Warren: They seem to have the secret.
Warren: They know how to do it. It's not a facade for them.
Debra: But they're maniacs!
Warren: Yes, but they're honest with each other. Everything's out in the open with them. [imitating Frank] "Eggs, Marie, and hold the chatter!" I love that! I'll tell you, they're the ones who oughta be giving the seminar.
- "The Ride-Along" has Marie freaking out over Robert putting Ray into a dangerous situation with an armed robber. Ray is impressed by Robert's bravery and professionalism in the situation, pointing out that Robert's job as a cop puts him in these dangerous situations all the time. Marie and Frank's reaction isn't funny at all.
Raymond: Stop! Robert's the one you should be worried about! Are you listening to me, Ma? He's the one who's out there everyday! He's the one who's risking his life-
Marie: I know what he does! I don't need to think about it!
Raymond: Okay, I just wanted you to know-
Frank: ENOUGH! Your mother doesn't like to think about it!
- "Sister-In Law", Ray is reduced to tears by Amy, after she rants to him about his lack of conversing with her. Granted he called her "annoying" first, but that was arguably the result of stress and pressure put on by his family.
- "Ray's Journal" is a really funny episode, but when you stop and think about it, yeah, it's pretty sad that all those years ago, Marie came across a journal entry of Ray's where he wrote, without any explanation, that he hated her. She never questioned Ray about it until the events of that episode, so it must have been in the back of her mind all that time, wondering why he wrote that.
Marie: (to Debra, who wants Marie to apologize to Ray for guilting him into apologizing for what he wrote) Imagine little Michael, who loves you, who lights up whenever you get near him. Now imagine him at 14, and he doesn't talk to you anymore. And you don't want to push him, so you just give him more love. And then one night you make him his favorite dinner, and you try to give him a kiss good night, and he goes up the stairs with a grunt. And you come across his journal, and you open it, and it says, "I hate my Mom." I wouldn't wish that on you, Debra.
Debra: Apologize to your mother.
Ray: ...I already did.
Debra: Do it AGAIN.
- The sad losses of Peter Boyle (Frank) in 2006 and Sawyer Sweeten (Geoffrey) in 2015.
- We can add Doris Roberts (Marie) to the list as well, sadly.
- "Sleepover at Peggy's": After the first Peggy episode, which portrayed Peggy as a Dean Bitterman Sitcom Arch-Nemesis, this sequel episode gives us surprising character development for Peggy, showing her as emotionally cold due to her divorce. It's hard not to feel a little sorry for her in the scene where she opens up to Ray about why she left her uncaring husband, especially since the one person she subtly came onto, Ray (by tapping his butt after he fixed the indoor tent), isn't going to leave Debra anytime soon.
- "Left Back" is one of the more serious episodes the show ever did, next to "Separation" and "The Garage Sale". The premise involves Michael not advancing as much as Jeffrey in pre-school and being recommended by the teacher that he repeat the year. Ray and Debra struggle with a Morton's Fork: Whether to rebuke the school's advice and let Michael advance despite not being mentally ready, or if they hold Michael back as suggested, whether to keep the smarter Jeffrey back as well so the twins don't get split up. While the teacher stresses that it's not as much of a shame to have kids repeat grades at such a young age, Ray can't help but feel Michael is dumb. This is especially true when Ray finds out Marie did the same thing to him as a young boy, leading him to think it runs in the family. It's a pretty heartbreaking episode, whether you've personally experienced the possibility of being left back or not.
- "Frank's Tribute" is another episode that runs on Fridge Sadness. Frank wins Man of the Year from his lodge, and Ray and Robert have to make a video tribute to him to show at the ceremony. The problem is that no one in the lodge has anything nice to say about Frank—no one. It's mostly played for laughs (Ray hits on the idea of asking the men how they feel about chocolate, and he and Robert then clumsily edit the video to make it sound like they're talking about their father), but think about it. Frank's been a member of the lodge since Robert was born; he considers these men close friends. But they still have nothing but anger and nasty comments for him. Granted, Frank's a Jerkass, but he also has a sweet side. It's lampshaded later in the episode when Frank storms out of his own tribute and complains that Ray and Robert did a bad job with it; Marie points out that he's actually upset that his so-called friends had nothing kind to say, and Frank is uncharacteristically speechless.
- In the same episode, Frank asks Marie what she would say in a tribute to him. She doesn't want to respond, and he eventually concedes with an "OK..." so soft and resigned that it's heartbreaking. Thankfully, she decides to answer to cheer him up.
- "A Date for Peter": Peter's conversation with Ray about his non-existent dating life:
Peter: You know something, Ray? When I first moved here, I said, "Okay, I am tired of being Mr. Lonely Jeans." So I went down to that bar down the street, and there were women there, and I sat for, like, two hours, and I finally force myself to go up to somebody and say, "Hey, how are you doing?" And she said, "Um, fine." And then the woman turned to her friends and said, "But I'm not desperate." And I just, you know, stood there while they laughed. And then I just, I walked home.
- "Surprise Party": While the material around it is funny, Lois's sudden "The Reason You Suck" Speech to Ray when he rejects her English tea party idea in favor of Debra's Chinese banquet idea, isn't:
Lois: Let's be honest. You're so uncomfortable around me. You never say more than two words. And it seems like whenever we are together, you'll do just about anything to get away from me. I mean, ugh, what am I supposed to think? You-you don't like me, you don't like my ideas. I just wish it were different between us.