Orange is the New Black, Netflix’s first foray into original programming, was a surprise smash. Showrunner Jenji Kohan (Weeds) based the series on Piper Kerman’s memoirs, Orange is the New Black: My Year in a Women’s Prison. Audiences instantly connected with the way in which the show humanizes prisoners, presenting the whole and empathetic people behind the crimes that put them away. In the first season, Kohan established the formula of character introduction, followed by a series of flashbacks showing defining moments or the circumstances that led to their incarceration. These vignettes are almost always poignant and demoralizing. Of course, there are plenty of awful things that happen to the inmates of Litchfield in the present as well. Kohan is a master at introducing likable people and then tearing their lives apart, and because we’ve grown to love these characters, the audience feels their pain in full force.

With season five now streaming, hardcore fans who’ve already done their binge-watching know that the emotional moments didn’t end with that season 4 cliffhanger. But here are 20 times Orange is the New Black proved to be particularly skilled at breaking our hearts.

(Since this is a list of plot points, it probably goes without saying that there are many massive spoilers for the previous seasons ahead, though none for the latest season.)

20. Bittersweet Swim In Freedom Lake

OITNB swimming in the lake in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

At the end of the show’s third season, some of the inmates are actually riding relatively high. In “Trust No Bitch”, Morello gets married, Piper gets revenge on Stella for stealing her underpants profits, and Poussey and Brook spark a relationship after the latter’s attempted suicide. But Litchfield is also in very tenuous transitional period, because Caputo has just accepted a corporate promotion instead of honoring his promise to head up a union for the guards. The prison staff walks off the job in protest, allowing the prisoners to discover a completely unguarded hole in the fence that leads to a lake.

Most of the main characters are outside when it’s discovered and slip through en masse, jumping into the lake for a therapeutic swim. Black Cindy is especially thrilled because, for proper conversion to Judaism, she needs to be baptized in a natural body of water. Floating, splashing, and laughing, the ladies are having so much fun, that they don’t notice their single beds being converted to bunks, nor the packed busses full of new inmates that pull into the already overcrowded prison. With the staff on strike and Caputo nestling into the pocket of MCC, Litchfield has never been more corporate. And corporations aren’t generally known for their humanitarianism.

19. Suzanne Attacks Poussey

suzanne 20 Times Orange Is The New Black Ruined Our Lives

Tired of the nickname “Crazy Eyes” and being misunderstood by her fellow inmates, the mentally and emotionally unstable Suzanne is ripe for the picking when season two’s Big Bad, Vee, arrives on the scene. Vee builds up Suzanne, and uses the rapport that creates to turn Suzanne against the other inmates. That includes sweet Poussey, who has never treated Suzanne, or anyone, poorly. Suzanne becomes fiercely loyal to the only woman she believes truly understands and supports her.

In “Little Mustachioed S***”, Poussey warns Taystee and Suzanne about Vee’s nefarious motives and brainwashing. Vee catches wind of it and gives Poussey an unspoken choice to turn over her hooch trade to Vee or become an enemy. When Poussey declines, Vee gets her fired from the library, one of the only fulfilling things in her life. Poussey later gets drunk and confronts Vee, and it sets off Suzanne, who gets the nod and promptly pummels Poussey into the bathroom floor. Poussey’s punishment for trying to help her friends see the truth about Vee is painful to watch. Especially because we know just how right she is about Vee.

18. Maritza’s Mouse Snack

OITNB Maritza eat a mouse or flies in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

Litchfield has never been a nice place, but things get practically apocalyptic when The Management & Correction Corportion (MCC) takes over and hires a group of unstable and sadistic guards. In “Turn Table Turn”, a particularly cruel CO named Humphrey brings Maritza, who has taken over Pennsatucky’s van driving job, to an abandoned house in the woods behind Litchfield to play a real-stakes version of “Would You Rather”.

Worse yet, it’s something he clearly plans way in advance. Earlier in the episode, he gives Maritza what she thinks is a hypothetical choice between eating dead flies or a live baby mouse. She chooses the mouse, because she imagines it would be like “eating a jelly bean”.

Off screen, he procures a collection of both creatures and gets everything all set up so it will be ready when they arrive. He holds a gun to her head and tells her that she must make the choice for real or die. Maritza, of course has done absolutely nothing to provoke Humphrey. He’s only tormenting her because he truly enjoys abusing his power and making people suffer. The look on Maritza’s face when she understands that there’s no getting out of this is absolutely tragic.

17. Taystee Shuns Poussey

OITNB Poussey vs Taystee in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

Vee does a lot of evil things, but one of her most egregious offenses is breaking up the greatest duo at Litchfield. Taystee and Poussey’s friendship is golden from day one. They have a jovial rapport and a seemingly unbreakable bond. But Taystee also feels an obligation to Vee, who was a mother figure to her on the outside (albeit a manipulative one). Poussey knows that Vee is bad news and tries to get her BFF to see it too.

Unfortunately, Taystee thinks Poussey is just jealous, and these formerly fun-loving pals have several tough-to-watch arguments. Then, Vee convinces Taystee to end their friendship as revenge for Poussey turning down Vee’s business proposal. This sends poor Poussey off the deep end, and she starts hitting the prison hooch harder than ever. They both struggle with their estrangement, and audiences experience withdrawal over the loss of the Statler and Waldorf of Litchfield.

16. Vee Tricks Suzanne

OITNB Suzanne in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

Vee, who could easily be the subject of her own list of nefarious deeds, spends a lot of time brainwashing Suzanne. Her hard work pays off for her unexpectedly when she realizes she can use Suzanne as her patsy. Red and Vee have an old beef from the latter’s precious incarceration. When Vee returns, she rekindles their rivalry by starting a competing smuggling businesses.

Their dispute comes to a head in “It Was the Change”, where Red unsuccessfully attempts to strangle Vee during an argument. Then Vee pretends to call a truce; they even shake hands over it. But handshakes are meaningless to Vee, who is devoid of a moral code. Later in the episode, she sneaks up behind Red and bludgeons her with a slock (a lock inside a sock). Red survives the attack, but is very badly injured. Vee convinces Suzanne that she is the one behind the attack and gets two of her followers to corroborate the story. When Vee is finally taken out, run over by a freewheeling Rosa, it’s bittersweet. Suzanne still believes that her emotional volatility is irreparable, and that she just lost the only person who could help her get better.

15. Sophia Sent to SHU for “Protection”

OITNB Sophia in SHU in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

Normally, none of the other inmates care about Sophia being transgender. In fact, she garners a great deal of respect on account of the miracles she works in her salon. Mendoza and Sophia even share a bond over their sons, who have begun hanging out together on the outside after carpooling together to Litchfield. But when the boys get into some trouble, Mendoza’s son bails on Sophia’s, leaving him to take the fall for a battery charge.

Sophia forbids them from seeing each other, and puts the kibosh on the carpool, leaving Mendoza’s son without a way to visit his mother. Mendoza is furious, and she spreads transphobic rumors around the prison, which leads to two prisoners attacking Sophia in a hate crime. When Sophia begs for protection, the bottom-line obsessed MCC makes a devastating call. Instead of reprimanding her attackers, and hiring more competent guards, they send Sophia to SHU, where she is left to rot in solitary confinement. Sounds real safe.

14. Piper Lies/Alex Doesn’t

OITNB Piper and Alex in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

The reason Piper is sent to prison in the first place is because Alex, her erstwhile girlfriend/drug mule business partner, rats her out. Later, Alex gets busted, and the pair makes up and rekindles their romance at Litchfield. In season two‘s first episode, “Thirsty Bird”, Piper finds herself mysteriously transported to Chicago. It’s there that she receives a message from Alex revealing that they’ve both been called to testify against Kubra, their recently extradited former boss. Alex is terrified of Kubra’s wrath, and implores Piper to commit perjury, and testify in court that she’s never met Kubra.

Piper spends the episode agonizing over the decision, and eventually decides to protect Alex, whom she deems “the love of [her] life”. Unbeknownst to Piper, Alex has decided to accept a plea that awards her parole for telling the truth. Since they’re separated, Alex never gets the chance to tell Piper about changing her mind. Knowing her, it’s highly likely that she would have thrown Piper under the bus either way.

13. Suzanne Fights Maureen

OITNB Suzanne and Maureen in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

In the first episode of season four, Suzanne and Maureen, who have been a very sweet couple up to that point, take the opportunity to run into the woods after their big swim. At first, they just want a little romantic alone time, but Maureen then gets the idea to run, and tries to convince a reluctant Suzanne to join her. With the guards on their way, Suzanne panics and leaves Maureen to get busted. Maureen incurs a harsh punishment, and she never forgives Suzanne for abandoning her.

Maureen’s resentment comes to a head in “People Persons”, when the sadistic guards exploit their tension during a lockdown. Humphrey, the Voldemort of prison guards, forces Suzanne to fight Maureen. The mentally unstable Suzanne gets carried away and nearly kills her former paramour. Wracked with guilt, Suzanne tries to atone by rigging a bookshelf to fall onto her. Maureen is the first girlfriend Suzanne has ever had, so to have it end so badly will surely have a lasting effect.

12. Ruiz Has The Worst Mother’s Day

OITNB Ruiz and baby in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

Mother’s Day is hard in prison, even if you don’t have a new baby on the outside. For a long time, Ruiz’s boyfriend, Yadriel, visits with their baby, Pepa. He sits stoically while Ruiz offers parenting advice and interacts with Pepa. Ruiz may be a criminal, but she’s also a loving and enthusiastic mother who only wants what’s best for her daughter. When she is nearly transferred to another prison, she begs the typically mum Yadriel to start speaking more around Pepa so that she doesn’t develop language issues. He complies and then Ruiz’s transfer is cancelled, so for one hot minute, it looks like everything will be okay.

That’s why it’s such a kick in the pants when he drops a bomb on his way out the door after their visit in “Mother’s Day”. As their daughter grows more cognizant of the outside world, Yadreil has become concerned about the emotional toll on Pepa visiting her mother in prison. Without any warning or discussion, he informs Ruiz that they won’t be visiting anymore. It’s already a done deal when he takes Pepa from Ruiz’s arms and walks past the guards. Ruiz is left sobbing in the hallway, watching her (presumably now ex) boyfriend carry their baby girl out of her life for the foreseeable future. Happy Mother’s Day.

11. Cavanaugh’s “Compassionate Release”

Orange Is The New Black Jimmy 20 Times Orange Is The New Black Ruined Our Lives

Due to their age, The Golden Girls of Litchfield are afforded certain freedoms simply because they are deemed harmless by the prison staff. But being ignored comes with a downside too. Jimmy Cavanaugh, who suffers from increasingly severe dementia, is often putting her own life at risk when she goes for her delusional strolls. She flies so far under the radar that, at one point, she is able to walk right out of Litchfield, winding up at a bar where Caputo’s band is playing.

In response to this incident, Caputo calls for shot quotas to encourage guards to become more aware of the prisoners, and to watch over Jimmy in particular. Unfortunately, it doesn’t stick.

In “Comic Sans”, Jimmy hallucinates that the chapel is a swimming pool, and she breaks her arm diving off the altar. In typical Litchfield fashion, they come up with a quick fix to their liability issue, without regard to consequences, and “award” Jimmy a “Compassionate Release”. Though she is basically delusional 100% of the time, they leave her at bus station with no money and nowhere to go. We don’t hear what happens to her after that, but there is no way it ends well.

10. Soso’s Suicide Attempt

OITNB Brook depressed in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

Brook Soso is almost bubbly when she first arrives at Litchfield, which immediately marks her for ridicule. She finds her place when she begins utilizing her activism skills from the outside to protest unfair treatment by the guards. At a certain point, Soso forms a rivalry with Leanne. After a major confrontation, Leanne cuts off Soso’s hair in her sleep, triggering Brook’s spiral into depression.

In “Don’t Make Me Come Back There”, she goes to Healy for help, but in a classic Healy move, he dismisses her, saying she just needs to go on medication. She is resistant to meds, because what she would really like is some emotional support. When Brook fails to find any, she acquiesces to the medication. But, at her wits end, she only agrees to it so that she can use the pills to overdose. Fortunately, Poussey finds her in time and saves her life. After that, Poussey and Brook find mutually beneficial support in each other. But then, of course, nothing good ever lasts at Litchfield.

9. Taystee’s Failed Parole

Taystee flashback in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

Fan favorite Taystee seems like one of the least likely candidates for incarceration. She’s smart, sweet, and sassy, but she also has a lot of baggage that holds her back mentally. Nevertheless, Taystee is so motivated to turn her life around that she earns herself an early release. Her fellow inmates are supportive and excited for her, and they throw her a big party the day before her release, as nobody expects to ever see her again.

In “F****giving”, her dreams are quickly dashed when she realizes everyone she knew on the outside is dead or in jail. She winds up crashing on the floor of a tangential relation. Instead of following her dream to become a paralegal, she finds a job at Pizza Hut and her minimum wage salary goes straight back to Litchfield, where she still has an outstanding balance. For Taystee, life is better in prison, where she has meals provided and friends who love and support her. So she intentionally violates her parole in order to go back “home”. This is really more of a systemic failure than any fault of Taystee’s, but it’s still heartbreaking to see her decide that she will never have the life she once envisioned for herself. In her mind, Litchfield is the best she can ever do.

8. Sofia’s Medication Woes

laverne cox orange is the new black 20 Times Orange Is The New Black Ruined Our Lives

For her transition, Sophia relies on a prescribed dosage of estrogen to keep her hormones in balance. But Litchfield, a privately owned and operated prison, is broke. In the show’s third episode, “Lesbian Request Denied”, prison management decides to cut corners by dramatically reducing Sophia’s prescribed dosage without warning, and her body and emotional state react poorly.

Desperate to get back to normal, she tries to scam estrogen off of a menopausal Sister Ingalls. But Ingalls realizes Sophia is only being nice to her because she needs something, and refuses to help. When Sophia does finally get her full meds restored later down the line, it’s a huge relief. She and Ingalls also develop a very sweet friendship. But in the meantime, without her meds, Sophia suffers greatly. This first glimpse into Sophia’s struggles, which also includes a flashback of her running credit card scams on the outside to fund her transition, really sets the tone for the show. Litchfield is an unjust and uncaring place.

7. Taystee’s Job Fair Letdown

OITNB Taystee job interview in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

In “Looks Blue, Tastes Red”, Figueroa sets up a mock job fair under the guise of helping inmates prepare for release. After her parole failure, Taystee sees the job fair as a shot at redemption. If this type of program were run in earnest, maybe people like Taystee would have a fighting chance on the outside. But the reality is that Fig could care less about the wellbeing of the inmates.

One of the reasons the prison is broke is because Fig has been embezzling funds to help with her husband’s campaign for state senate. She sets up the program for publicity, in an attempt to draw attention away from her shady bookkeeping. Taystee nails the interview with Phillip Morris, and is told that she got the job — only there is no job. Taystee gets nothing for her trouble but more disappointment and an increased feeling of hopelessness. In the same episode, we also meet Vee in a flashback, foreshadowing the fact that things are only going to get tougher for our dear sweet Taystee.

6. The Truth About Christopher

OITNB Morello in a veil in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

When we first meet Lorna Morello in season one, she seems eccentric and casually bigoted, but mostly harmless. She and Nicky have a fling, but Morello breaks it off out of guilt over her fiancé, Christopher. She spends the rest of the season dropping casual mentions about Christopher and their impending nuptials.

But in the second season episode, “A Whole Other Hole”, Lorna receives a phone call from her sister informing her that Christopher is engaged to another woman. She spirals emotionally as we learn, through flashback, that Morello and Christopher were never really a couple. They go on one date, after which he breaks it off. Morello, on the other hand, is smitten and remains in denial about their relationship. She stalks him and, after he files a restraining order, she plants a bomb in his new girlfriend’s car. No one is hurt, but this crime leads to Morello’s incarceration.

None of the other inmates are aware of the real story, or that, during one of Rosa’s cancer treatments, Morello drives the prison van to Christopher’s house, takes a bath while wearing his fiancé’s veil, and steals a teddy bear. The delusion continues, and every mention of Christopher from here on out is that much more tragic.

5. Nicky Is Sent to Max

OITNB Nicky Max Morello and Red in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

Nicky is always there to help fellow inmates through their struggles, so it’s extra hard to watch her battle with her heroin addiction. At the start of season one, she’s been clean for three years thanks to Red, who acts as a mother figure when her biological mother has given up on her. But the ultra evil drug dealer Vee sees Nicky’s addiction as a business opportunity, so she tasks Taystee with giving Nicky a “sample” bag of heroin to secure a customer base.

Nicky works so hard to resist, but after Vee attacks Red, Nicky is angry and steals Vee’s supply for revenge. In the third season, Nicky still has Vee’s heroin and wants to unload it to make her temptation moot. She teams up with Luschek, a CO she trusts, and he agrees to help her sell it. But in “Empathy is a Boner Killer”, Caputo finds the heroin in Luschek’s desk and Luschek throws Nicky under the bus to save himself.

They send Nicky to Max, which the inmates always refer to as the kiss of death. Red and Morello, Nicky’s two closest confidantes, catch up with her as she’s escorted out. They’re tearful, panicked, and hurt that Nicky didn’t come to them for help. They exchange final declarations of love, but the look on Nicky’s face as she walks toward the van says that she doesn’t believe she’s worthy of their love and never will be.

4. Pennsatucky’s Rape

OITNB Pennsatucky and Coates in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

When we first meet Tiffany “Pennsatucky” Doggett, she’s an unstable religious zealot who sees Piper as her rival. But she starts to grow emotionally after a stint in psych and a violent beating from Piper. It’s not until the third season that we really get to know Pennsatucky and learn about her miserable upbringing.

Her mother teaches her that sex with men is merely a joyless transaction, and a compulsory one at that. Teenage Tiffany acts accordingly, until she meets the kind and dashing Nathan. They fall in love and he shows her adoration and sexual pleasure that she never thought possible. When Nathan must move away with his family, she falls into a slump and is subsequently raped by a former sexual partner. This incident is echoed when Coates, a CO that has been plying her with stale donuts and generally taking advantage of her, confuses his feelings for her and rapes her out of anger and frustration.

Up to that point, she had been making progress in Litchfield. She was starting to find peace and even made a friend in Big Boo. But after Coates has his way, you can see the light going out of her eyes, and the painful resignation across her face.

3. Poussey’s German Girlfriend

OITNB Poussey confronts German officer in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

Poussey Washington has a big heart. She also has a strong bond with Taystee, but because of their incompatible sexual orientations, they can never be more than friends. This leaves Poussey generally lacking in romantic prospects. A flashback in “You Also Have a Pizza” depicts a 17-year-old Poussey as an army brat living in Germany and falling in love for the first time.

She has a sweet romance with Franzi, the daughter of a German commander, and it’s uplifting to see Poussey’s romantic feelings reciprocated. But when Franzi’s father walks in on them having sex, he is furious and blames Poussey for corrupting his daughter. In order to split Poussey and Franzi apart definitively, he re-assignes Poussey’s father, sending the Washington family back to the United States.

Before they leave, Franzi tearfully confesses her love to Poussey, who responds with disingenuous detachment – a defense mechanism she has clearly used before. But this time, it doesn’t stick. Poussey becomes so distraught that she obtains a gun and confronts Franzi’s father on Ice Cream Thursday. Poussey’s own father intervenes before she has a chance to pull out the weapon and, in the process, reveals to her that he accepts her as she is. The tears were already flowing by then, though.

2. Poussey’s Death

OITNB Poussey death in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

The show spends a lot of time endearing the audience to Poussey. By season four, she is easily the show’s moral center. She’s made some mistakes, but they’ve always come from the heart. She only ever wants happiness for her loved ones, and she finally finds her own happiness in a relationship with Soso. It’s going so well that they start making plans to be together when their sentences conclude. Successful TV chef/inmate, Judy King, even promises Poussey a job on the outside.

So yeah, it should have been obvious that something very bad was going to happen to her. In the season’s penultimate episode, “The Animals”, Poussey gets caught in the middle of a brawl while trying to help calm a panic-stricken Suzanne. Bayley, an inexperienced CO, restrains Poussey, but he’s so distracted and frightened by Suzanne’s continued hysteria that he doesn’t notice Poussey struggling for breath beneath him. Taystee sees Poussey in trouble, and Coates also tries to intervene, but they’re both too late. Poussey is already gone by the time anyone can get to her. Taystee’s grief is palpable as she curls up sobbing next to her dead best friend. They lay side by side, as they’ve done in their bunks so many times.

1. Every second of “Toast Can Never Be Bread Again”

OITNB Poussey flashback in Orange is the New Black 20 Times Orange Is The New Black Ruined Our Lives

Season four’s final episode is a real bastard. Harsh story beats abound as the inmates are still reeling from the unexpected loss of Poussey. Suzanne and Maureen have an awkward reunion in medical together after their violent confrontation. Alex is insane with guilt for having killed her would-be assassin. Poussey’s body is still lying in the cafeteria, and Caputo won’t call her father because they’re too busy trying to find dirt on her in order to shift blame. And, of course, there’s the riot that Taystee incites after Caputo refuses to fire Bayley, the CO responsible for Poussey’s death.

The trigger-happy Humphrey reaches for his gun, but Maritza, probably still thinking about that mouse he made her eat, kicks it away. In a split-second decision, Daya picks it up and aims it at his head. To the prisoners, Humphrey represents everything that’s wrong at Litchfield. They’ve experienced so much inhumane treatment, that they’ve finally all snapped. What punishment could be worse than the lives they already lead?

But it’s Poussey’s flashback that’s the real kicker. Depicting a young and carefree young woman adventuring around New York on her last night before moving to Amsterdam, it’s inarguably the most optimistic flashback the show has ever done. It might even have been a respite from all the present-day heartache if not for this smiling girl who is now a ghost. Her past was full of possibility, but in the present, all of her prospects have been suffocated.

Did we miss any of the most heartbreaking OITNB moments? Let us know in the comments.

Season five of Orange is the New Black premieres June 9th, 2017 on Netflix.

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