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99 Problems is the 17th episode of Season 5. It aired on April 8, 2010.


Dean Purgatory Blade.png.png There was something about being there... It felt pure.

This episode summary is an official CW press release. It may contain errors.

Sam and Dean are outnumbered by demons, but are saved at the last minute by Rob (guest star Michael Shanks) and his townspeople, who are aware of the Apocalypse, and have been training to fight and kill demons. The small town is very religious and Sam and Dean meet Pastor Gideon (guest star Larry Poindexter), who introduces them to his daughter Leah (guest star Kayla Mae Maloney), whom he claims is a prophet. Leah tells the townspeople they must obey her orders if they want a spot in Heaven but when she starts turning the townspeople against each other in the name of the Lord, the brothers realize they must kill her.



The Winchesters are speeding down the road, battered and being pursued by demons. Sam is wounded and urging Dean to drive faster but he has to slam on the breaks after taking a turn that ends at a fiery barricade. When the demons pounce and attempt to drag them out of the car, three people in a water truck appear and turn the hose on them.

The SLM give the demons a holy water hosedown.

As the demons sizzle, one of the group recites an exorcism rite through a megaphone and the demons immediately smoke out. The man makes sure the stunned Winchesters are okay, warns them to be careful and says there's no need to thank them when the boys call after him to find out who they are. They are the Sacrament Lutheran Militia, he says, then calmly informs them that those were demons and that the Apocalypse has begun.

The boys convince their rescuers that they know all about demons.

After they reveal the hunting arsenal in their trunk and convince the militia members that they're on the same team, the Winchesters are invited to follow them back to their town. They arrive at their church in Blue Earth, MN, where many are gathered for a wedding ceremony, officiated by Pastor Gideon.

The pastor later meets the boys and shows them to the command center in the church basement. He tells them the whole town is armed against the swarms of demons; the pastor himself is strapped with a side arm and young children are packing salt rounds. He says they were forced to take such measures because the demons were killing them.

The Winchesters meet Leah Gideon.

When asked why they didn't call in the National Guard, he says they were told not to, but refuses to say by whom. They press him, noting that the exorcism that they invoked at the roadblock was Enochian and therefore had to have been provided by an otherworldly source. He maintains that he can't discuss it, but his daughter, Leah, interjects: "It's okay, Dad. It's Sam and Dean Winchester. They're safe." She says she knows all about them, thanks to the angels. The boys are not happy to hear they've been the subject of angel communiques, but Leah assures them that the Enochian warding etched into their ribs is keeping them cloaked. She says the angels have been showing her where the demons are and how they can protect themselves against them through visions. They verify that she receives these visions through severe, flashing headaches, as reported by the last prophet they encountered (in The Monster at the End of This Book).

Sam waits for Dean's answer to a core question.

Later, Sam tries to reach Castiel via phone but ends up leaving a message asking for his help. He and Dean are at Paul's bar where business is brisk; Paul comments to Sam that it's been like one long 'last call' ever since the end of the world began. As Sam and Dean discuss why the demons seem to be targeting Blue Earth, Sam expresses scorn toward the angels for having these people do their demon dirty work, with little regard for their lives. Dean, however, has become resigned about the world's end and reckons that since at best it'll be only a couple of months before everyone dies, it's not such a bad thing that these folks are "running to the exits in an orderly fashion," instead of freaking out. Annoyed by Dean's defeatism, Sam sharply asks "Who says they're all gonna die? What ever happened to us saving them?" Dean seems rattled by the question and before he finds a response, a bell rings in the distance and the bar patrons start filing out of the bar.

Leah filters a vision through Pastor Gideon.

On his way out, Paul explains the church bell is the signal that Leah has had another vision.

They go to the church where Leah, by whispering to her father, announces the whereabouts of a group of demons sheltered on the outskirts of town and Pastor Gideon calls for volunteers to join him in dealing with them. Rob is the first to raise his hand and Paul is next, joking that someone needs to cover Rob's ass, and Dean volunteers himself and Sam. As the pastor leads a prayer for protection, Sam notices that instead of bowing his head to pray along with everyone else, Paul pulls out a flask and raises it to a disapproving Rob before taking a swig.


The group consisting of Pastor Gideon, Rob, Rob's wife Jane and son Dylan, Paul and the Winchesters, descends on the demon house. With varying combinations of rock salt rounds, exorcisms, holy water backpack-sprayer blasts, hand-to-hand combat and the demon-killing knife, they eliminate the demons therein.

The SLM + Winchesters emerge from their battle with the demons.

As they emerge, Sam and Dean acknowledge how nice it is to have proper backup for once. Dylan gets his parents' okay to ride back to town with the guys and as the others drive away, Dean tosses him a beer in appreciation of his having saved him in two close scrapes in the house.

The boys discover too late that one demon escaped.

As Dylan leans against the Impala and takes a sip, he is pulled to the ground by his ankles and dragged underneath the car. Dean races around to help him while Sam drags the demon out from the other side and kills it, but not quickly enough to save him.

Jane aims her grief at Dean.

At Dylan's funeral, Dean offers condolences to Jane and Rob as they arrive, but grief-stricken Jane hisses "This is your fault." As Pastor Gideon tries to offer some words for Rob and Jane, Leah collapses from the front pew and appears to have a seizure. When it passes, she declares that Dylan is coming back.

Leah receives the first installment of the angels guide to receiving paradise.

She regains her composure and calmly tells Rob and Jane they will see Dylan again because he will be resurrected on Judgement Day. She goes on to tell the congregation that together, they all will see their loved ones again because the angels have chosen them to receive paradise on Earth. All they have to do is follow the angels' commandments, which include no drinking, no gambling, and no premarital sex.

Sam is surprised Dean's okay with going vice-free.

As they exit the church, Sam tries to gauge Dean's reaction to hearing that a few of his favorite things have just been outlawed. When Dean's response is basically non-responsive: "Yeah, well, whatever... when in Rome," Sam is quizzical. Dean offers only that he's neither cool with it, nor not cool with it, because it isn't his call. He turns to go back inside the church, telling a slightly confused Sam that he'll catch up with him later.

Leah unnerves Dean with her diagnosis of his heavenly status.

Dean returns to talk to Leah wanting to know if she is legitimate and to find out exactly what the angels have been telling her about paradise. She tells him about the destined "prize-fight," which will be really bad, but that "we" will ultimately win. When that happens, the planet will be handed over to the chosen and finally become a peaceful place where you're surrounded by the people you love, a world devoid of monsters, disease and death. When Dean sadly comments that it must be nice being chosen, Leah replies that he is chosen. He scoffs, "Yeah, more like cursed." As he rises to leave, she comments that it must be hard for him to being the Vessel of Heaven, but having no hope. He is visibly affected by her remark.

Paul and Sam drink to being the only two drinkers in town.

Sam revisits Paul's bar and finds him there all alone. He tells Sam the Apocalypse is no longer good for business since "Leah's angel pals" put the kibosh on the town's popular pastimes. Paul loves and will protect his hometown, but has no time for holiness. Sam comments he did happen to notice his rebuff of the prayer earlier; Paul confides that half of the guys in the militia are the same way, and until recently could still be found boozing and/or banging the nanny, but now they've become "warriors of God." He's not sure if there is a God or not, but he has never prayed and believes it would be hypocritical to start now. He asks Sam if he is a true believer; Sam says he does believe in God, but is pretty sure that he has stopped caring. Dean is sitting soberly in the motel room when Sam stumbles in. He admits he's been drinking, and says he would still be at it if not for the newly established curfew. He alerts Dean to the fact that all the cell towers in town have been shut down, and all internet and cable access has been blocked toward the goal of eliminating the "corruption of the outside world."

Sam tries to talk Dean back from abandoning their mission.

Sam expects him to be as incensed as he is that the angels have people wound so tightly that they're turning their town into a fundamentalist compound, but to his surprise, Dean is projecting only weary indifference. "Angel world, angel rules" is his assessment, likening the world to the Titanic with the angels holding all the lifeboats. Dean doesn't see how or by whom everyone is to be saved, because it was supposed to be them, but they can't do it. Sam cannot abide Dean's surrender and pleads "You can't do this." Dean solemnly replies, "Actually, I can." Sam keeps at him, reiterating that there's no one else he can count on, and he cannot do it alone. Dean decides he needs to clear his head and walks out, ignoring Sam's warning that it's past curfew.

Leah conveys the angels' angry message.

At the church, Pastor Gideon is working alongside other militia members when Leah enters, panicked. She tearfully tells him that the angels are angry and say they can't go to paradise. They don't understand why, since they've been doing as they're told. Leah says the angels are furious because some individuals aren't following their commandments. Rob asks her to name names. Dean is still out walking when he hears shouting and shattering glass inside Paul's bar. He finds Paul and Rob tussling amid a group of townspeople, with Pastor Gideon trying to pry a baseball bat away from Rob.

After fighting demons together, "the chosen" turn on their own.

Dean asks the pastor if he needs a hand and he responds by calling for everyone to just cool down. Paul asks how can he cool down when his friends are trying to run him out of town? Rob shouts that he needs to leave, for the greater good; he's sorry, but says it's not their choice. "That's bull," says Paul, reminding Rob they grew up together and that he stood up at his and Jane's wedding.

Jane eliminates Paul as a roadblock to paradise.

Jane chimes in, coldly declaring that was then, but now he's "standing against the flock" of true believers. Paul rejects that, pointing out that he fights with them. When Rob tells him not to make this any harder for them, he rejects that as well and reminds them that Blue Earth is his home, too, and makes it clear that the only way they will remove him will be to drag him out. When Rob moves to make that so, Dean clocks him to prevent it. As the two of them struggle, Jane shoots Paul dead, declaring that no one will stop her from seeing her son again.

Castiel arrives, in no mood to answer stupid questions.

Meanwhile, at the motel, Castiel finally arrives in response to Sam's voicemail, drunk and a bit surly. He admits to Sam that he found a liquor store, and drank it. As Sam starts to describe the demon attacks, Castiel asks if there's any sign of angels. Sort of, says Sam, through visions channeled through prophet Leah Gideon. Castiel immediately corrects him—the names of all the prophets are seared into his brain, and Leah Gideon is not one of them. Dean returns to the motel room with the news of Paul's killing."It's starting," says Castiel. He and Sam inform him that the being impersonating Leah is actually what the Book of Revelation identifies as the Whore of Babylon, who rises when Lucifer walks the earth "bearing false prophecy," and possesses the power to take human form and read minds.

Castiel educates the boys on the Whore of Babylon, as written in Revelation.

He says the demons attacking the town are actually under her control; the so-called exorcism she provided is fake and actually translates as Enochian blue humor. Their "smoking out" and the promises of paradise are part of the manipulation to achieve exactly what Dean witnessed: innocent blood spilled in God's name. Her goal is to condemn as many souls to Hell as possible. "Alright," says Dean with a bit of new found energy, "how do we go pimp of Babylon all over this bitch?"

Jane seeks reassurance that she's still chosen.

In the church office, Jane and Rob are seeking counsel from "Leah." Jane is sobbing, extremely fearful that by gunning a man down on his own property for selfish reasons, she may have angered the angels further and made things worse. "Leah" assures Jane that the angels understand what she did was for the greater good, because Paul was a sinner who would have dragged the rest of them down with him.

"Leah" sows more seeds of doubt among the flock.

Pastor Gideon overhears this exchange and voices his disbelief that Jane's heinous sin could be okay with the angels. "Leah" counters that it's not a sin to strike down evil. As he starts to protest further, she interrupts him by reminding him that he's always taught her to have faith. The pastor is stunned.

Castiel obtains the required weapon, a stake made from a Babylonian cypress tree. He informs Sam and Dean it's not a simple matter of just anyone ventilating her, however, because the stake must be wielded by a true Servant of Heaven in order for it to kill her. Because Castiel's defiance has separated him from Heaven, Dean refuses to submit to the will of the angels and Sam is considered an abomination, the three of them do not qualify.

Leah warns Pastor Gideon to back off, or she'll sic "the chosen" on him.

At the church, Leah holds the full attention of the congregation as Pastor Gideon pastor nervously stands off-side. She calmly informs them that the final judgment is to commence at midnight, but the angels have warned her they are not quite ready; there are still a few sinners among them "that need to be taken care of." The pastor realizes she's frightening everyone and tries to inject calm, but Leah continues telling them she's been given instructions and a list of names, and time is running out.

"The Whore" takes a moment to admire herself.

When he grabs her and tells her to stop it before someone gets killed, she warns him to unhand her, or else he'll be the next sinner she names. As he leaves the church discouraged, Castiel appears to him and identifies himself as an angel of the Lord before teleporting him to the motel room where Dean and Sam await. They explain why, as a true Servant of Heaven, he must be the one to complete the task. He says there's no way he could kill his daughter; they point out that it's not his daughter, who's probably been dead for months, it is the thing that killed her.

The pastor is a reluctant participant.

They perceive he already knows deep down it's not Leah, and stress that if doesn't kill it, innocent people are going to be killed and the others damned to Hell.

As Castiel sits outside the hotel later, Dean offers him some hangover meds. Still despondent since learning his search for God was futile (in Dark Side of the Moon), he asks Dean, self-described expert on "dead-beat dads," how he manages. "On a good day," Dean says somberly, "you get to kill a whore."

Jane and Rob are just following orders.

At the church, Jane and Rob are among those who have apprehended people named on the list of "sinners," as instructed. Once they are all locked the store room, they are instructed to get the kerosene. Jane hesitates, protesting that there are children in the group.


"Leah" says firmly that the angels have provided their names for a reason, and convinces Jane by adding that her son needs her to do it. When the Whore is next alone in the church office, Castiel appears and restrains her for Pastor Gideon to stake. She whimpers to the pastor as his daughter, causing him to hesitate long enough for her to utter an Enochian spell that floors Castiel and leaves him writhing in pain. She kinetically flings the pastor and the Winchesters across the room and runs out into the common area. The pastor recovers and pursues her, but she screams to the others that he is a demon. When they seize him, the cypress branch goes flying. She quickly orders Rob and Jane to burn the people in the store room, but Sam manages to pummel Rob and restrain Jane before they can ignite the kerosene.


The Whore knocks Dean on his back and applies a choke hold; when she sees he's grabbing for the stake just out of his reach, she sneers and berates him as a pathetic, self-hating, and faithless so-called servant of Heaven who is just going to sit back and watch the end of the world. Dean finally stretches far enough and grabs the stake, plunges it into her torso with a twist and snarls "Don't be so sure, Whore."


Everyone witnesses the Whore's true visage as she convulses and glows; the stake flames up and finally explodes as she expires. Jane wonders out loud how they will get to paradise now, Dean tells her he's pretty sure she's headed in a different direction.

Sam wants reassurance of Dean's stance on the Michael question.

As the boys support the wounded Castiel and pastor to get them out of the church, Sam wants to know how Dean was able to vanquish the Whore, noting she could only have been ganked by a Servant of Heaven. Dean tries to attribute it to luck, but Sam wants him to say he's not planning to do something stupid, as in "Michael stupid." Dean acts as though he's offended by the suggestion, but Sam looks worried. His fear is realized later, when on the pretense of going to get bandages from the trunk, Dean jumps in the Impala and speeds off, leaving frustrated Sam in the parking lot yelling after him.


As he drives, Dean decides to visit Lisa Braeden. She is surprised to see him and asks if he's okay; he somewhat awkwardly tells her that even though he accepts his life and has no illusions about how it will likely turn out, he just wanted her to know that whenever he imagines himself happy, it's with her and Ben. Lisa says she wants that, too, and tries to get him to go inside and talk, protesting that he can't just stop by and drop a bombshell like that, and leave.


He tells her he's sorry, but he can't stay. He decides to warn her that in the next few days, things are going to get worse than bad, but not to worry because the people he is going to see next will not get what they need from him unless they agree to a few conditions, and he's making arrangements for her and Ben. Confused, she begs him not to do whatever it is he's thinking of doing, but he says he has to. He kisses tearful Lisa goodbye and leaves.


Main Cast[]

Recurring Cast[]

Featured Supernatural Beings[]


  • Lisa Braeden was last seen in the Season 3 episode Dream a Little Dream of Me.
  • The news that God no longer cares about the Apocalypse is having detrimental effects on both Dean and Castiel. Dean is thinking about saying Yes to Michael, and Castiel has taken up heavy drinking. Due to his willingness to serve as Michael's vessel, Dean is now a True Servant of Heaven.
  • Castiel says to Pastor Gideon: "I'm an Angel of the Lord". He said exactly the same thing to Dean when they first met in Lazarus Rising. In this episode, however, he is drunk, demoralized, and bitter, and sounds almost disgusted with himself, making for an extremely humorous comparison.
  • Dean said "Since the angels got the only lifeboats on the Titanic." Ironically, the Winchesters encounter a situation where the angels actually scuttled the Titanic in My Heart Will Go On.


  • This episode's name comes from the fact that this is the 99th episode of the series and is the 99th problem the Winchester brothers have faced on-screen. The name of the episode also makes a reference to the song "99 Problems" by Jay-Z.
    • Jay-Z must be feeling sorry for them, as a bitch was one of their problems.
  • Michael Shanks who guest-stars in this episode as Rob is best known for playing the character of Dr. Daniel Jackson from Stargate SG-1. Other actors from the Stargate series are known to play characters throughout the show, notably Julie McNiven (Anna Milton), Mitch Pileggi (Samuel Campbell) and Amanda Tapping (Naomi).
  • The town the episode takes place in, Blue Earth, Minnesota, previously appeared in Salvation. It was the location of Pastor Jim Murphy and where he was killed by Meg.
  • When Sam and Dean are drinking in the bar, the town bell rings and everyone leaves Dean says "was it something I said?". This may be a reference to a similar incident occurring to Leon in Resident Evil 4.

Featured Music[]

  • "Too Hot To Stop" by Marc Ferrari and Steve Plunkett


  • Dean: What is she exactly?
  • Castiel: The Whore.
  • Dean: Wow, Cass, tell us what you really think.

[Sam tries calling Castiel on his cell phone]

  • Automated message: You have reached the voice mail of-
  • Castiel's voice: I don't understand. Why-why do you want me to say my name?

  • Sam: No drinking, no gambling, no premarital sex? Dean, they basically just outlawed 90% of your personality.

  • Sam: What's wrong with you? Are you... drunk?
  • Castiel: No...[Sways a little]...Yes.
  • Sam: What the hell happened to you?
  • Castiel: I found a liquor store...
  • Sam: And?
  • Castiel: And I drank it.

  • Dean: And the Enochian exorcism?
  • Castiel: Fake. It actually means "You breed with the mouth of a goat."

[Sam and Dean stare at him]

  • Castiel: ...It's funnier in Enochian.

  • Castiel: The Whore can only be killed by a true servant of Heaven.
  • Dean: Servant, like?
  • Castiel: Not you, or me. Sam of course is an abomination. We'll have to find someone else.

  • Castiel: Pastor David Gideon?
  • Pastor Gideon: Yeah, who are you?
  • Castiel: (drunk and dejected) I'm an Angel of the Lord.
  • Pastor Gideon: ...Yeah, sure.

Pastor Gideon: Why does it have to be me?
Castiel: You're a servant of Heaven.
Pastor Gideon: And you're an angel.
Castiel: (bitterly) Poor example of one.

[The Whore/Leah has Dean pinned to the ground. He reaches for the Cypress stake.]

Leah/Whore: Please. Like you're a servant of Heaven. This is why my team's gonna win. You're the great vessel? You're pathetic, self-hating, and faithless. It's the end of the world. And you're just gonna sit back and watch it happen.

[Dean stakes her with the Cypress branch]

Dean: Don't be so sure, whore.

[After the Whore is killed]

Jane: But I don't understand. How are we supposed to get to Paradise now?
Dean: (grimly) I'm sorry. Pretty sure you're headed in a different direction.

Sam: Are you going to do something stupid?
Dean: Like what?
Sam: Like Michael stupid.


International Titles[]

  • German: 99 Probleme (99 Problems)
  • Hungarian: 99 probléma (99 Problems)

External Links[]