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| Episode 1 - [Italy Part 1] |
| Details : When Marie surprises the family with the news that she's treating them all to a two-week vacation in Rome everybody loves the idea – except Raymond. It's virtually impossible not to enjoy oneself in a country as beautiful as Italy; but if anyone can manage it Raymond can. Not willing to let his sour mood spoil it for the rest of the family Debra Frank Marie Robert and the kids go on their merry way and soak up the atmosphere sights smells and tastes of the city of love and try their best to ignore Ray. Meanwhile Robert meets the girl of his dreams – she's stunningly beautiful unbelievably sexy and works in a gelato shop. |
| Guest Cast and Crew : David Proval | Alex Meneses | Silvana De Santis as Aunt Colletta | Pierrino Mascarino as Giorgio | Sergio Sivori as Italian Man #1 | Vanni Bramati as Italian Man #2 | Writer : Philip Rosenthal | Director : Gary Halvorson | |
| Air Date : Oct. 02, 2000 |
| Episode 2 - [Italy Part 2] |
| Details : When Marie surprises the family with the news that she's treating them all to a two-week vacation in Rome everybody loves the idea – except Raymond. It's virtually impossible not to enjoy oneself in a country as beautiful as Italy; but if anyone can manage it Raymond can. Not willing to let his sour mood spoil it for the rest of the family Debra Frank Marie Robert and the kids go on their merry way and soak up the atmosphere sights smells and tastes of the city of love and try their best to ignore Ray. Meanwhile Robert meets the girl of his dreams – she's stunningly beautiful unbelievably sexy and works in a gelato shop. |
| Guest Cast and Crew : David Proval | Alex Meneses | Rosario Coppolino as Pizza Guy | Vincenzo Vitagliano as Bocce Player | Silvana De Santis as Aunt Colletta | Pierrino Mascarino as Giorgio | Writer : Philip Rosenthal | Director : Gary Halvorson | |
| Air Date : Oct. 02, 2000 |
| Episode 3 - [The Wallpaper] |
| Details : Ray finally tells Frank and Marie how he feels about their constant intrusiveness after Marie accidentally drives the car through the front of his house. |
| Guest Cast and Crew : Annie Abbott | Patricia Belcher | Writer : Lew Schneider | Director : Gary Halvorson | |
| Air Date : Oct. 09, 2000 |
| Episode 4 - [Meant To Be] |
| Details : Robert finds himself in the most unlikely position of having to choose one of three women – girlfriend Amy ex-wife Joanne or Italian bombshell Stefania – to share the future with him. Robert decides that honesty is the best policy when it comes to his relationship with Amy so he foolishly tells her about his recent reunion with ex-wife Joanne. To make matters worse when Amy runs to Debra for consolation Debra mistakenly spills the beans about Robert's recent tryst with Stefania. Suddenly Robert is not in a position to decide which woman he wants. It's a matter of which one if any is going to want him. |
| Guest Cast and Crew : Monica Horan as Amy | David Proval | Suzie Plakson | Alex Meneses | Writer : Kathy Ann Stumpe | Director : Michael Zinberg | Writer : Jennifer Crittenden | |
| Air Date : Oct. 16, 2000 |
| Episode 5 - [Pet Cemetery] |
| Details : Ray inadvertently commits petslaughter on Ally's hamster while Debra and the kids are away for the weekend. When Ray breaks the difficult news to Ally about Pumpernickel's untimely demise Debra insists that they give the beloved pet a proper burial -- complete with eulogies -- to help the youngster get through the grieving process. What Ray at first thought was an utterly ridiculous way to mourn the passing of a family pet ends up being one of the most emotional experiences of his life. |
| Guest Cast and Crew : Director : Ken Levine | Writer : Steve Skrovan | |
| Air Date : Oct. 23, 2000 |
| Episode 6 - [The Author] |
| Details : The competition for attention between Ray and Robert reaches an all-time high with the brothers ending up in a fight. Ray's dreams of authoring a sports book get squashed when the publishing company takes a pass on it just as Robert receives the good news that he is being promoted to lieutenant. The Barone family doesn't quite know how to react to this most bizarre of situations in which Ray has failed at something while Robert has succeeded. But worst of all Ray doesn't know how (or if) he's ever going to get past this. |
| Guest Cast and Crew : Director : Andy Ackerman | Writer : Mike Royce | |
| Air Date : Oct. 30, 2000 |
| Episode 7 - [The Walk To The Door] |
| Details : Ray is mortified when he meets a girl whom he dated 25 years earlier and believes he treated with disrespect. Meeting Elizabeth again Ray wracked with guilt because he feels he didn't behave properly on their high school date is determined to apologize. However when he finds out the real reason Elizabeth went out with him that night long ago he regrets ever bringing up the past. Meanwhile Debra demands that Ray give her an example of something he regrets but incredibly he can't come up with anything. |
| Guest Cast and Crew : Fred Ornstein | Director : Asaad Kelada | Writer : Tucker Cawley | |
| Air Date : Nov. 06, 2000 |
| Episode 8 - [Young Girl] |
| Details : While celebrating Thanksgiving Debra discovers that her seemingly contented parents are really not very happy with each other. When Ray accidentally overhears his in-laws going at it with each other he relays the news to Debra... who has always believed her parents' relationship to be a lot healthier than Frank and Marie's. But when things come to a head at the Thanksgiving table it's apparent that there really isn't that much of a difference between the two older couples – much to Debra's dismay. |
| Guest Cast and Crew : Writer : Kathy Ann Stumpe | Director : Michael Zinberg | |
| Air Date : Nov. 13, 2000 |
| Episode 9 - [Fighting In-Laws] |
| Details : Robert starts to date a 22-year old woman and Marie and Debra don't think it's right. They break up when he finds out that she's really only 19 and she finds out that he's really 43. |
| Guest Cast and Crew : Katherine Helmond as Lois Whelan | Robert Culp as Warren Whelan | Director : Michael Zinberg | Writer : Tom Caltabiano | Writer : Aaron Shure | |
| Air Date : Nov. 20, 2000 |
| Episode 10 - [The Sneeze] |
| Details : Ray gets sneezed on at the airport and he fears he might have caught something so Debra tries to take care of him but Marie takes over. |
| Guest Cast and Crew : Bob Joles | Director : Ken Levine | Writer : Steve Skrovan | Writer : Aaron Shure | |
| Air Date : Nov. 27, 2000 |
| Episode 11 - [Christmas Present] |
| Details : Ray buys Debra an elaborate Christmas gift in the hopes that she will be so impressed she will let him go on a weekend golf trip with his buddies. Ray believes he has the whole scenario worked out – give Debra a better gift than she is getting him – and soon he'll be teeing off on a new course that he's been dying to play. However he doesn't figure on the even more extravagant gift that Debra has purchased for him. |
| Guest Cast and Crew : Jon Manfrellotti | Writer : Kathy Ann Stumpe | |
| Air Date : Dec. 11, 2000 |
| Episode 12 - [What Good Are You] |
| Details : When Ray doesn't react to Debra's choking everyone makes fun of him so he tries to be more attentive in relative situations. |
| Guest Cast and Crew : Susan Varon | Director : Ken Levine | Writer : Jennifer Crittenden | |
| Air Date : Jan. 08, 2001 |
| Episode 13 - [Super Bowl] |
| Details : Ray is mortified when he realizes that Marie used to read the personal journal he kept as a teenager. When Marie blurts out an embarrassing incident from Ray's past he can't figure out how she could have possibly known that information. That is until he discovers that she must have broken the secret code he used when writing in his journal. And in the process his mother has learned about his most personal and perverted thoughts. |
| Guest Cast and Crew : Jon Manfrellotti | Writer : Jennifer Crittenden | |
| Air Date : Jan. 29, 2001 |
| Episode 14 - [Ray's Journal] |
| Details : Ray gets to go to the Super Bowl and cover it for his newspaper. He brings Gianni but feels bad about not having brought Debra when he sees that all the other reporters brought their wives so he has her flown in and to prove that he wants to spend time with her he rips up the tickets to the Super Bowl. |
| Guest Cast and Crew : Director : Gary Halvorson | Writer : Mike Royce | Director : Kenneth Shapiro | Writer : Ray Romano | |
| Air Date : Feb. 05, 2001 |
| Episode 15 - [Silent Partners] |
| Details : Ray and Debra discover that they have nothing to talk about except the kids. |
| Guest Cast and Crew : Director : Gary Halvorson | |
| Air Date : Feb. 12, 2001 |
| Episode 16 - [Fairies] |
| Details : Ray is upset when he finds out that Debra signed up Michael and Geoffery to play fairies in a school play. |
| Guest Cast and Crew : Diana Maria Riva | Matt Romano | Writer : Tucker Cawley | Director : Gary Halvorson | |
| Air Date : Feb. 19, 2001 |
| Episode 17 - [Stefania Arrives] |
| Details : Robert gets a surprise visit from Stefania the woman with whom he fell head over heels in love when the Barones vacationed in Italy. Robert's excitement over having his beloved and stunningly gorgeous Stefania so close quickly gives way to annoyance when he is witness to a few of her idiosyncrasies. After spending some quality time with the Italian beauty sans gelato and gondolas Robert has to rethink his feelings for her. Meanwhile Stefania's father who has accompanied her to America has his own change of heart with respect to his feelings for Robert. |
| Guest Cast and Crew : David Proval | Alex Meneses | Susan Varon | Writer : Tucker Cawley | Writer : Lew Schneider | |
| Air Date : Feb. 26, 2001 |
| Episode 18 - [Humm Vac] |
| Details : Ray purchases a new state-of-the-art vacuum cleaner from an attractive door to door saleswoman and it ignites a housekeeping war between Marie and Debra. Debra is as taken with the new vacuum as Ray once she witnesses all of the wonderful things it can do. That is until she learns why the saleswoman showed up at their door in the first place. Determined to prove to Marie that she's is just as good at keeping house Debra attempts to use the new vacuum to find some dirt any dirt in Marie's home. Of course the results are disastrous |
| Guest Cast and Crew : David Proval | Writer : Lew Schneider | Director : Gary Halvorson | |
| Air Date : Mar. 19, 2001 |
| Episode 19 - [The Canister] |
| Details : Marie gathers Robert's ex-girlfriends Amy and Stefania and his female police partner Judy together so they can dissect his character in an effort to help her better understand why her eldest son can't commit to a relationship. Unfortunately Robert unexpectedly drops in and is forced by his mother to listen to his character being assassinated by the women as they discuss his relationship hang-ups in detail and compare notes on his quirky dating behavior inability to commit to one woman and his flawed personality. |
| Guest Cast and Crew : Monica Horan as Amy | Writer : Jennifer Crittenden | Director : Gary Halvorson | Writer : Mike Royce | |
| Air Date : Apr. 09, 2001 | Rating ➦ ★★★★★★★ |
| Episode 20 - [Net Worth] |
| Details : Debra becomes angry when Ray contributes $1000 without first consulting her to his friends' harebrained scheme to open a go-cart business. |
| Guest Cast and Crew : Brian Posehn | Bob Odenkirk | |
| Air Date : Apr. 23, 2001 |
| Episode 21 - [Let's Fix Robert] |
| Details : When Ray and Debra find Frank painting their house they find out that Marie put him up to the job due to his retirement. But when Frank paints it the color they don't like Ray fires him. That's when Marie reveals the truth behind Frank's retirement. |
| Guest Cast and Crew : Monica Horan as Amy | Sherri Shepherd | David Proval | Alex Meneses | Writer : Scott Buck | |
| Air Date : Apr. 30, 2001 |
| Episode 22 - [Say Uncle] |
| Details : When Ray realizes that his kids would rather spend time with their Uncle Robert than with him he decides to do something about the situation. When Robert makes the observation that as a parent Ray finds it boring to be around his kids Debra couldn't agree more. She then suggests that Ray follow Robert's example and to try to have more fun with his children. But when her own parenting skills are called into question by Marie Debra quickly changes her tune and rallies behind Ray insisting that they are both very involved parents. |
| Guest Cast and Crew : Renee Faia | Writer : Aaron Shure | Director : Kenneth Shapiro | |
| Air Date : May. 07, 2001 |
| Episode 23 - [Separation] |
| Details : Debra gets upset when she finds out that her parents have seperated. |
| Guest Cast and Crew : Katherine Helmond as Lois Whelan | Robert Culp as Warren Whelan | Tom McCleister | Director : Asaad Kelada | Writer : Philip Rosenthal | |
| Air Date : May. 14, 2001 |
| Episode 24 - [Frank Paints The House] |
| Details : Debra becomes angry when Ray contributes $1000 to his friends' hair brained scheme to open a go-cart business without first consulting her. |
| Guest Cast and Crew : Writer : Jason Gelles | Director : David Lee | |
| Air Date : May. 21, 2001 |
| Episode 25 - [Ally's Birth] |
| Details : As Ray escorts Ally to a father-daughter dance he realizes how grown up and independent his daughter has become. As a result he begins to recall the day nine years ago when the Barone clan welcomed her into the family but not without incident. In the flashback expectant parents Ray and Debra are caught by surprise when Debra goes into labor in the back seat of Robert's patrol car forcing him to be called into action. Meanwhile Ray and Debra plot to keep a pushy Marie away from the delivery room until after the baby is born not an easy feat. |
| Guest Cast and Crew : Writer : Tucker Cawley | Director : Jerry Zaks | |
| Air Date : May. 21, 2001 |