Orange Is the New Black: Most Heartbreaking Moments, Ranked

    Orange Is the New Black is a comedic drama based on the memoir Orange Is the New Black: My Year in a Women’s Prison written by Piper Kerman, whose name is uncoincidentally the same as the protagonist. Orange Is the New Black has not only been one of Netflix’s most popular shows of its time, but it is also its longest-running series and has racked up countless nominations. The hit show was the first series to earn nominations in both the comedy and drama categories.

    Orange Is the New Black tells the story of an upper-middle-class white woman sentenced to 15 months in prison after her ex-lover named her an accomplice to a crime they committed together 10 years prior. This sentencing forces Piper to meet her ex face to face in prison which is ultimately conflicting because even though Alex is the reason she’s been ripped from her cushy life, she still has feelings for her.

    As the show unfolds, inmates’ stories, struggles, relationships, and crimes unfold as well showing the humanity, corruption, and pain within the prison’s walls. As expected, this show has moments that warm viewers’ hearts, but more often moments that break them.

    10 Lolly’s Crime


    Officer Healy was a contradictory character in the show, but overall had good intentions. He has some soft spots and the biggest one was an inmate who reminded him of his late mother as they had the same mental illness, Lolly Whitehill (Lori Petty). He took Lilly under his wing and when she murdered an officer, he convinced her and himself that she didn’t actually kill him, that she’d made it up in her head.

    In a jail full of cameras, a secret like that can’t stay hidden very long. She was eventually sent away to the psychiatric unit at a maximum-security prison. Their separation was the moment she was dragged away, and it was heartbreaking to see another mentally ill inmate slip through the cracks and to hear the betrayal in her voice as she called out for him.

    9 Lorna’s Loss

    orange is the new black

    While Lorna was a spunky character full of moxie in the beginning of the series, the hardships of incarceration slowly wear her down. One event in particular was the final straw for her already fragile sanity. Lorna and Vinnie get pregnant, and she couldn’t be more excited to be a mom, even if from behind bars. This fantasy came crashing down when Vinnie informed Lorna that their baby boy, Sterling, came down with pneumonia and his tiny body couldn’t fight it off.

    Related: Orange Is the New Black: Best Episodes, Ranked

    This reveal was heartbreaking, but the behavior that followed absolutely shattered the audience’s hearts. Instead of grieving the loss of her baby, Lorna acted as if nothing was wrong. She couldn’t cope with losing him and not being with him when he passed, so her mind protected her by believing that her baby boy was safe and sound. This is one of many examples of the idea that some inmates need mental health care instead of prison.

    This moment was also heartbreaking because Lorna wasn’t permitted to go to her son’s funeral, but Piper was permitted a weekend leave for her grandmother’s.

    8 Nicky Getting Sent Away

    Natasha Lyonne as Nicky- Orange is the New Black

    Throughout the series, Nicky, portrayed by Natasha Lyonne, is a teddy bear that has razor-sharp edges. She was a big caretaker for her prison family, but helping them fight their demons didn’t diminish her own. Throughout the series, she struggled with drug addiction, and that came to a head in Season 3 when a new inmate gave her access to heroin that she used and then tried to sell.

    She eventually got caught and was sent to a maximum-security prison for essentially an entire season. The heartbreaking part of the moment was that inmates and viewers alike had no idea if their beloved Nicky would return.

    7 Sophia’s SHU

    Laverne Cox in Orange is the New Black

    Sophia Burset, played by Laverne Cox, was an inmate in the show who like in real life is transgender. She was a maternal and warm figure in the prison, but not one to be messed with. Her rival Gloria (Selenis Leyva) made unsavory allegations against her that resulted in Sophia being sent to a special housing unit (SHU) which is another way of saying solitary confinement.

    Even though Gloria had no real evidence that Sophia was a danger to the women in prison, the guards decided to lock her away out of laziness. There, Sophia was left to live in deplorable conditions, in isolation for an inhumane amount of time. After her release from isolation, her spark was diminished.

    6 Vee’s Destruction

    Vee Parker

    The same inmate who provided Nicky with drugs, Vee, caused a lot of damage prison-wide. Although many of the prisoners had a lengthy list of flaws, most of them also had redeemable qualities. That was not the case with Vee. She was manipulative and took advantage of Suzanne (Uzo Aduba) a vulnerable inmate struggling with her mental health.

    Vee tricked Suzanne into believing she cared for her which resulted in Suzanne doing a lot of Vee’s violent dirty work, landing Suzanne in trouble and a lot of emotional duress after Vee got what was coming to her. There were a lot of heartbreaking moments caused by Vee, but possibly the worst one was the aftermath of her emotional abuse of Suzanne after her death.

    5 Red’s Deterioration

    Kate Mulgrew as Red on Orange is the New Black

    Galina “Red” Reznikov (Kate Mulgrew) was an inmate who was the true maternal figure of these misfit inmates. A Russian woman with a passion for cooking, she ran the kitchens and took care of her girls. She started the series as a force to be reckoned with as she ran the kitchen and had significant power in the prison. Her grudges are the root of her downfall.

    After a feud results in her losing her job in the kitchen and being sent to the SHU, she deteriorates quickly. She develops dementia that her time in solitary confinement exacerbates quickly. Watching a powerful, maternal woman fall into nothingness is hard to watch.

    4 Staged Suicide

    orange is the new black tricia

    Itemizing heartbreaking moments in Orange Is the New Black makes it very apparent that this show, based on a memoir of the author’s real experiences in prison, thematically tends to expose corruption in the prison system. In the first season, Tricia Miller (Madeline Brewer) is a young inmate who struggles with drug addiction. In a sane world, drug addiction shouldn’t be possible in prison because there shouldn’t be a way to get drugs in.

    Related: These Are Our Favorite LGBTQ+ TV Characters of All Time

    To make matters worse, the drugs were smuggled in by the guard of all people. Officer Mendez made money from smuggling drugs into the prison and forced Tricia to help him. When he blackmailed her into taking drugs and those same drugs killed her, she avoided all responsibility by making it look like a suicide and making her out to be another stereotypical statistic about troubled women.

    3 Suzanne’s Mistakes

    Orange Is the New Black People Persons

    Suzanne is the source of a lot of heartbreak on the show. After recovering from Vee’s manipulation, she meets and falls for another inmate, Maureen (Emily Althaus). She is very susceptible to manipulation and just like with Vee, this vulnerability gets her into trouble.

    The guards manipulate Suzanne and her confusion results in her unintentionally hitting Maureen. While it seems like there could be a happy ending when the two reunite and make up in the hospital, it’s all for nothing because Maureen dies from the injuries Suzanne gave her.

    2 Pennsatucky’s End of Life

    Taryn Mannin as Tiffany in Orange is the New Black

    Pennsatucky was a fiery character throughout the series, except in her final days. She was unfiltered, but grew immensely throughout the series, becoming a fan favorite, so her cruel end was all the more painful. She was sexually assaulted by a prison guard and it broke her spirit.

    Early in the series, she was vengeful and fought for what she wanted, but after this tragedy, she lost her fighting spirit and eventually took her own life.

    1 Poussey’s Death

    Samira Wiley as Poussey- Orange is the New Black

    The most heartbreaking moments of the entire series surround Poussey’s (Samira Wiley) death. Poussey died violently and senselessly at the hands of one of the “good guy” guards. She was trying to calm down Suzanne, who everyone knew could become violent when upset. The guard saw Poussey as a threat and in retraining her, he murdered her.

    She died trying to help another inmate and because of that, the systemic violence her death represented, and overall, how loved she was, a riot broke out in the wake of her murder. As if that moment alone wasn’t heartbreaking enough, Poussey’s best friend and eventual girlfriend Taystee delivered a gut-wrenching speech to the press about the mistreatment of inmates within the prison as well as heartbreak as she mourned the person most important to her.

    The heartbreak in this show is sad to watch because viewers grow to live the characters, but devastating because these issues, murders, and heartbreak are daily struggles at prisons in America.

    Orange Is the New Black is available to stream on Netflix.


    Latest articles

    Related articles

    Leave a reply

    Please enter your comment!
    Please enter your name here

    carre carre carre carre carre carre carre carre carre carre carre carre