The hit sitcom Everybody Loves Raymond has no shortage of zany characters, and none are zanier than the quirky brother of Amy, Peter. Ever since his first appearance as a comic book store owner, Peter quickly became a memorable character despite showing up late in the series. Both his original actor, Paul Reubens, and his replacement, Chris Elliott, brought a uniquely silly sensibility to the character and the show as a whole.

Peter can be hilarious and oddly likable, with his distinct brand of whimsical comedy. Yet, he can also be irritating thanks to his crazy antics, his dislike of Robert, and his tendency to stir the pot when it comes to the Barone-MacDougall relationship. Still, there are at least a few moments that make it easy to sympathize with—and even pity—this sort of “black sheep” of the family.

10 Felt Bad For Him: Ray Getting In The Way Of His Mingling With Peggy

While it’s pretty much implied beforehand, the episode “A Date for Peter” establishes that this awkward comic book shop owner doesn’t tend to have much luck with the opposite sex. This makes it all the more frustrating that Ray essentially tries to derail Peter’s attempt to get to know a party guest at Ray and Debra’s place.

Even if the woman in question is Ray’s “arch-nemesis” Peggy, it’s a disrespectful move, to say the least. This is especially detestable given Peter’s history of being alone even as he’s pushing 40, not to mention his favoritism of Ray.

9 Hated Him: Refusing To Leave Robert And Amy’s Place

Shortly after Robert finally gets married to Amy, it becomes apparent that he’ll have to deal with her annoying brother far more frequently. In fairness, this episode, called “Peter on the Couch,” actually has some sympathetic moments for this black sheep character, as well.

Still, it begins in irritating fashion as it shows Peter hanging around these newlyweds seemingly for days and generally being a pest. Not only this, but Robert is basically pressured into driving him all the way home across state lines.

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8 Felt Bad For Him: His “Indoor Cat” Being Put Outside

During the aforementioned episode, Peter gets a rather disheartening revelation when he sees his parents storing all of his belongings in preparation for an apparent purge of all things Peter. But, one particularly harsh moment is when it’s revealed that Peter’s cat, wholesomely named “Miss Puss,” has been booted out of the house.

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This would be bad enough, but Peter then notes that his pet isn’t even an outdoor cat. Even if Amy’s brother can be annoying, conniving, and nasty at times, this is a pretty brutal, saddening scene.

7 Hated Him: Exploiting Ray At The Comic Book Shop

One humorous fan-favorite Raymond episode involves Ray making a trek across town to secure a beloved trading card for his daughter, which is essentially a cheeky knock-off of Pokémon.

While there are many chuckle-worthy moments, Ray has a particularly rough go of it here. He’s pressured into driving a great distance in the pouring rain, eating nothing but dry Cheerios in his car. As if this weren’t enough, Peter, then conceptualized as Russell, takes advantage of him by selling the coveted card at a steep price and pressuring him to buy some comics on top of it. He spends much of the episode toying with him before eventually getting him to shell out hundreds of dollars.

6 Felt Bad For Him: Being Talked About And Ostrisiced

Peter’s isolated, outcast status gets reinforced for much of the episode “Peter on the Couch.” Adding insult to injury, after he’s been essentially rejected by his own parents, he ends up standing around alone in the Barone household. There, the family talks about him behind his back, discussing what they should do with him.

This does lead to a sentimental moment, as it causes him to make a connection with Robert, who’s sort of a “down on his luck” outcast himself. In fact, Robert even suggests he check out his old apartment for a place to live. Still, the scenes leading up to this feel-good conclusion are pretty sad for Peter.

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5 Hated Him: Poking Fun At Ray With Peggy In This Own House

As it was mentioned, Ray has a pretty ugly moment himself when trying to get in the way of Peter and Peggy’s conversation at the cocktail party. Still, it doesn’t exactly warrant Peter’s response, which is to essentially make fun of him along with Peggy in tag-team fashion.

Not only is this being done under Ray’s roof, but Ray and Debra had gone out of their way to arrange this party basically so Peter could find a date. He closes this out by shouting that the Barone’s are “freaks” and that he’s not like them as Peggy’s leaving.

4 Felt Bad For Him: Getting Snubbed At A Bar

Despite this one taking the form of a story told by Peter, it still manages to be one of the harsher, more somber moments for this character and his fans. As he describes it, he had attempted to approach a woman at a bar and strike up a conversation.

After asking how she was doing, she had apparently answered with “fine” before muttering to her friend “but I’m not desperate.” Ouch…

3 Hated Him: Trying To Turn His Parents Against Robert

Peter exhibits some behavior that can be considered aggravating and repellent. Yet, this behavior verges on “irredeemable” in an episode that features Robert going to Pennsylvania to ask Amy’s parents for her hand in marriage.

Following this long trip and respectful gesture, Robert is then met with rudeness by the MacDougalls, especially from Peter. Not only does he accuse and belittle him, but he even reveals private details about their relationship to his parents. Despite his humorous nature, many viewers found it tough to like this saboteur after this cringy moment.

2 Felt Bad For Him: Getting Thrown Out Of His House

As it was partly established earlier, one of the most sympathetic moments for Peter’s stint on Raymond comes from his own parents. Robert and Peter make the long trip to his home, only to find that they’re eagerly packing all of his things, have put his cat outside, and have basically forced him to move out.

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Given that he’s been a fairly ostracized character as it is, this is a sad moment, even for those that aren’t too crazy about him. Not only this, but his beloved comic book store is also in a bad way at this point, making this a pretty rough low point for the character.

1 Hated Him: Trying To Sabotage Robert’s Wedding

In fairness, it’s actually Robert’s own mother who ironically ends up being the biggest nuisance at his wedding. Still, it becomes clear that Peter isn’t fully on board during Robert and Amy’s big day. Ray even has to watch over him for much of the event. This proves at least somewhat warranted when Peter ends up “forgetting” to pick up the priest who was to conduct the ceremony, forcing him to hitchhike.

When confronted, his reaction makes it pretty clear that this was intentional. So, basically, he was willing to sabotage his own sister’s wedding… Stay classy, Peter!

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