Prison bars slam, and Regina Spektor starts to sing. The opening credits for Netflix’s Orange Is the New Black feature her aptly named song “You’ve Got Time,” which was written specifically for the show and underscores stills and clips of actual former female inmates’ faces, setting the scene for a comedy about criminals. Though OITNB, which returns for a fourth season on June 17, is generally billed as a dark comedy, the right music choices set up certain key moments to be wholly devastating.

Of course, OITNB is rife with well-curated musical moments, from Rosa hitting Vee with the prison van as Blue Öyster Cult plays — “always so rude, that one” — to tUnE-yArDs soundtracking Piper’s first entrance into the “ghetto” dorm. These are nine of the most shattering.

"This Is Not A Love Song," Katie Cruel

Season 1, Episode 1

Piper was slated for a breakdown from the show's beginning. Forced starvation and the dawning reality of her incarceration is bad enough; to see Alex looking down at her as she struggles to breathe is downright awful. The eerie backing track here only heightens the anxiety and shock of the first episode’s close.

"O Come All Ye Faithful"

Season 1, Episode 13

As tensions collide to close out Season 1, Pennsatucky, dressed as an angel and wielding a stake-cross, is attacked by Piper as “O Come All Ye Faithful” starts to play. After this beating, we know Litchfield’s changed her. Pre-prison Piper is gone, and she’s not coming back.

"Beautiful," Christina Aguilera

Season 2, Episode 2

This song is a little different: Taystee sings it. To prospective foster parents. At a fair. This moment isn’t heartbreaking in itself — when another girl steps in, Taystee warns her to “back the fuck off” — but it is when you let it sit. Why sing Christina Aguilera? To impress. Taystee craves approval, and the lack thereof leads to her relationship with Vee.

"Almost Paradise," Mike Reno & Ann Wilson

Season 2, Episode 4

Although Morello is a stalker, and Christopher is her victim, and we see that she genuinely loves him, it’s painful to watch. “Almost Paradise” captures this exact fanciful sentiment, the hallmark of her worldview. We can see how the reinforcement of her idealized notions of love (hearing the song) can trigger a disastrous event.

"Into the Unknown," Blackchords

Season 2, Episode 7

Although Jimmy's compassionate release is said to be overexaggerated, the event in the show is fairly horrifying. As Jimmy is shuttled away, two things become clear to Piper: that there might be something worse than prison, and that her fate may very well be out of her hands.

"Come On Up to the House," Tom Waits

Season 2, Episode 9

Here, the song enters the scene as Piper confirms her newly ousted "criminal" identity. This melancholy moment pits the enjoyment of her temporary freedom against the knowledge that her furlough has almost ended. Tom Waits’s voice serves first as a mourning; then, through Piper’s thought process, turns contemplative.

"Coming Down," Dum Dum Girls

Season 3, Episode 3

Taken to Max, Nicky is stopped by Red, who demands to know why Nicky didn't come to her amid her addiction. Nicky responds, “Because that’s what I do, OK? I love you.” Nicky’s inability to fully escape from her addiction follows her into Litchfield as it’s followed her through flashbacks, again wearing down the relationship between her and those around her. The result? We end the episode feeling utterly hopeless.

"Good Old Mountain Dew," The Womenfolk

Season 3, Episode 10

As the scene fades out, the tune seems upbeat, but then you realize: Good old Mountain Dew means something sinister. This assault sweeps us right back to Pennsatucky’s childhood (her mom forcing her to drink an entire bottle of Mountain Dew) and her late adolescence, trading sex for six-packs. Like many others, we see Pennsatucky as caught in a cycle of manipulation.

"Too Dry To Cry," Willis Earl Beal

Season 3, Episode 12

Transgender prisoner Sophia’s had to fight hard to become a woman. She's attacked by women who ask if she “still has a dick” and later sent to solitary “for her own protection," showing how the prison system fails to address these problems. The worst part? None of it was her fault.