A TV series does not last 14 seasons without having a spark that keeps the viewers coming back year after year. This episode was everything that makes Supernatural, Supernatural. It had loss, hope, a little sprinkle of magic, and of course… self-sacrifice.
The episode opens up as a bedridden Jack continues to worsen. He asks Sam, Dean, and Castiel not to be sad about his impending death. He suggests that this might be the way things are supposed to be, but Dean does not believe that. After Jack goes into a coughing fit, Dean leaves the room as he is unable to just sit by and watch. Jack asks Sam to tell Dean that it’s okay, but Sam shrugs him off saying that Jack can tell Dean himself when he comes back. Jack wants to know what happens when a Nephilim dies, but Sam doesn’t have any answers for him. Always hopeful, Jack accepts this, saying that it will be an adventure. Castiel follows Dean into the hallway outside and tells Dean that even though it isn’t fair, Jack needs Dean to be there for him in his last moments. Accepting this, they both go back into the room, but it is too late…Jack is gone. Roll Titles (and a very sad moment for everyone).

Outside of Jack’s room, Castiel suggests they start thinking about next steps and Dean tells them Jack would have wanted a hunter’s funeral (Having A wake and burning the body). Sam abruptly leaves and when Castiel goes to follow, Dean stops him saying that Sam needs space. Dean leaves Mary a voicemail telling her what happened (which is honestly a dick move because Jack and Mary had gotten close in Apocalypse World and the least he could do was wait to tell her in person). As Dean is talking, we see Sam packing a bag and Castiel watches as he walks out the bunker door. Dean then walks up to Castiel and asks where Sam is.

Cut to the interior of a car (not Baby, since Sam took her). Dean reprimands Castiel for letting Sam go off by himself when he is clearly upset. Castiel reminds him that Sam needed space, but Dean replies that Sam needs space in the bunker with his family. They find Baby idling in the middle of the road with Sam sitting on the ground. Dean fears that Sam made a deal (remember Crossroads Demons?), but Sam replies that he was going to make a pyre. We then see, in a flashback, Sam cutting down a tree when his axe breaks. He feels like a failure because he can’t even properly gather the wood for Jack’s funeral pyre. Sam wants to know what good any of their vast resources and lore are if they couldn’t save Jack, and Dean tells Sam he was there for Jack and that is what’s important. Castiel adds that this doesn’t feel right; other deaths seem natural, and even if they are hard, he can understand it. However, Castiel cannot accept that Jack’s time would end so soon, especially since it ended before his own.

Dean decides that they will say goodbye tomorrow, and tonight they will get drunk and reminisce. We then get a beautiful montage of the boys doing exactly that. They empty bottle after bottle while talking and laughing and remembering the good times with Jack until, one by one, they leave; with Dean being the last one remaining.

After he gives a toast to Jack, we then cut to Jack who is standing around Baby with Dean, Sam, and Castiel. The gang is eating burgers outside a small café and working on a case. As Dean begins to show Jack how to read a paper map, he starts to “glitch” and Jack realizes that something is wrong. He then exits through a door and finds himself in the white hallways of heaven. However, he is barely able to look around before he sees a black goo cascading down the hallway and is forced to run for his afterlife.

Dean awakens at the table in the bunker, massively hungover from last night. He goes looking for everyone else and finds Castiel and Sam talking to an old woman whom Castiel introduces as Lily Sunder [If you recall from Season 12, Lily was a human who had a Nephilim daughter and Castiel was among a group of angels that were sent to “eliminate the threat”. After her daughter’s death, Lilly worked for a century honing black magic to stay young and exact revenge on those Angels she held responsible]. Lily is an old woman now, after having stopped using magic a while back, and Sam called her because he believes she might be able to help.

Currently, no one has been able to translate the Angel Tablet (remember that plot device?) since there is no longer a prophet to reach out to at the moment. As Lily had spent years studying Angel magic, Sam hopes that she can understand the tablet and find a way to bring Jack back. Unfortunately, she is not able to; however, she suggests using her own magic to bring Jack back. Jack’s human body died, but his soul is still in heaven and Castiel can go to heaven to bring Jack’s soul back to his body for a few seconds. In that moment, the magic can keep Jack here, but a small piece of his soul will be used up in the process. No one likes the idea, but Lily assures them that using such a small piece won’t have any effect and no one can think of any other way to bring Jack back. Dean (always the skeptic) asks what this will cost; Lily admits that because she’s killed Angels, she knows she is not going to heaven, so she wants Sam and Dean to change that in exchange for Jack’s life.

Team free-will have a sidebar to discuss their options and they all have different opinions. Dean does not want to risk Jack’s soul, Sam is okay with it since it’s just a small part, and Castiel thinks that Jack should decide what happens. Dean then asks how they would even go about getting Lilly into heaven as they are not on good terms with Billie/Death or the reapers. Castiel informs them that Death just collects the souls and they have no power to decide where they go. The being they need to talk to is Anubis, the Egyptian Guardian of the Dead. When God left, Heaven needed a new judge and Anubis was the obvious choice, so the gang decides to summon him (because, hey… they’ve summoned Gods before).

Meanwhile, in Heaven, a little girl is playing fetch with her dog in a beautiful garden. Her dog takes a while to return, but when it does, Jack is with him. The little girl asks who he is, and Jack replies that he is her son. We then see the girl shift into a grown-up Kelly, and Mother and Son finally embrace for the first time. Jack explains to Kelly that she is in Heaven, in her memories, and Kelly then remembers her death. However, she soon realizes what Jack being here means and Kelly tells Jack that Castiel and the others were supposed to look after him. Jack tells her Castiel and everyone tried their best to save him, but it didn’t work.

Back on earth, the boys are getting ready for the spell, and Dean is still worried because he does not trust Lily. Sam tells him that they don’t really have any other options and to not try would be like letting Jack die all over again. Castiel then enters and tells them that “Angel radio is playing a distress signal”; it seems that ALL of Heaven’s gates are open, and that cannot be good. Dean and Sam agree to work with Lily on this end while Castiel checks out Heaven and gets Jack. They paint a sigil on the floor to trap Anubis, and Lily gives Sam a book with instructions for when Jack wakes up so he can complete the spell. Sam goes to grab one last thing, leaving Lily and Dean alone. Dean tells Lily that something has been bothering him; She stopped using her magic to stay young, knowing it would accelerate her inevitable end in hell, so why did she stop? She tells him that she only has one small sliver of her soul left; and because of that, she wants to be able see her daughter in heaven. Continuing to use her magic would burn up that last bit of soul, which means she would never be able to be with her daughter again.

Castiel soon arrives in heaven, appearing in a white hallway with black smudges of goo all over the floor. He finds two Angels laid out on the floor with the black substance leaking from their nose and eyes. Dumah (an angel we first met in season 13) is still conscious, but very afraid. Castiel asks what happened and she tells him that the black stuff touched her, everything went black. Castiel tells her he is looking for Jack and she begs him not to leave her; he helps her up, and they both go off together (Yes Castiel, trust the one survivor of a massive attack without question; I’m sure there is nothing suspicious about her at all!).

They then go to Jack’s heaven, but he is not there; instead Naomi is, and she tells them that Jack left. Castiel asks her what happened, and she replies that they were overwhelmed by the shadow that rules the Empty (a.k.a. Castiel’s Doppelganger from last season). Naomi believes it wants Jack because he is half Angel and Naomi suggests they give it what it wants. Castiel refuses and Naomi reminds him that if they don’t, heaven will fall and all the of human souls there will be lost. However, before any more arguments can be made, the Shadow begins to consume Naomi and she tells Castiel to run.

Back at the bunker, Sam and Dean summon Anubis. The Egyptian God is cool and collected and he immediately recognizes the brothers as their names have come across his desk many times. Anubis asks what they want, and Lily asks him where she is going after she dies. Despite the fact that it is against protocol, Anubis agrees to check. He pulls out an abacus and has Lily put her hand over it. Immediately the beads start to move and settle more on the black side, signaling Lily’s destination as Hell. Anubis apologizes, but even when the Winchesters threaten to leave him imprisoned, he tells them he can’t change a person’s fate. The only person who can make a difference is Lily, as her choices throughout her life are what matters and nothing anyone else does can change that. Realizing there is nothing else he can do, Sam scuffs the sigil and releases Anubis.

Back in heaven, Castiel continues his search for Jack in Kelly’s Heaven as he knows that is where Jack would go. Jack and Kelly are hiding out in her house; and once Jack sees that it is Castiel at the door, he lets him in. Everyone embraces and Castiel apologizes to Kelly for failing to protect Jack, but Kelly assures him that he didn’t. Jack asks Castiel what he is doing there and Castiel tells him about the plan to use his soul. Kelly is worried about the risk, but Castiel also explains that the Shadow of the Empty will destroy heaven looking for Jack; if Jack is gone, then the Shadow will leave. Dumah then enters and tells Castiel that that is smart before revealing that she is actually the empty possessing her body (Wow, what a shock! Totally did not see that one coming).

After the ordeal with Anubis, Lily is packing and getting ready to leave. Sam tries to convince her to stay, but she refuses to as that wasn’t part of the deal. Dean tells her that he thinks with her soul is so gone, she is not even human anymore. If Lily had any humanity left, she wouldn’t just sit around and watch someone else lose a child like what happened to her.

Back in heaven, the Shadow (still in Dumah’s body) demands that Jack goes with it. She obsesses over the fact that dead Angels belong to her and she delights in mentioning to Jack that where he is going is worse than Hell. The Shadow relishes in Jack and Kelly’s fear because it wants to hurt Castiel for waking it up and escaping from the Empty. Castiel then pulls out an angel blade to attack it, but it easily sends him flying across the room. Cut back to the bunker and Jack’s body is being prepared to receive his soul. Lily is looking at a locket with her daughter’s picture and after a few moments, she kisses it and tells the brothers that she is ready to begin. Cut back to heaven and Dumah/The Shadow is beating a prone Castiel on the floor. Kelly is horrified by the fight and tries to intercede, but she is thrown backward. Cut back to Earth, and Dean prays to Castiel to let him know they are ready as Lily starts reading the spell.

Back in Heaven, Castiel hears Dean’s prayers as Jack approaches the Shadow. She effortlessly grabs Jack by the throat and Castiel struggles to his feet. He tells the Shadow to take him instead of Jack, as Castiel was the one who woke up the Shadow (and is thus, whom the Shadow really wants). However, the Shadow is not convinced because Castiel will already go to the Empty when he dies. Castiel reminds that his death might not be for a very long time; but, if it lets Jack go, Castiel will go right now. More importantly, Castiel will go willingly. The Shadow agrees to this, but it won’t take him now. It wants him to suffer, and in order to do that, Castiel needs to go back to his life; for when he is finally happy and content, that is when the Shadow will take him to the Empty. Castiel accepts, and the Shadow departs Dumah’s vessel. Jack asks Castiel why he would do that, and Castiel responds he made a promise and that both he and the Winchesters love him. Castiel then asks Jack to keep this a secret so as not to worry the brothers, and he promises not to tell. Before Jack returns to earth, he embraces his mom again, wishing they had more time. Kelly tells him to have a great life and that they will see each other again. Castiel then approaches Jack and touches the sides of his face; He starts to glow and then…

…We cut to earth, as Jack awakens coughing and gasping. He reads the incantation Lily left and his eyes illuminate as a piece of his soul burns away, stabilizing him and saving his life. The Winchesters go to thank Lily, but they see her body dead; she used up the last of her reserves to save Jack. She appears in Anubis’ office and he invites her to re-test the abacus. This time, they settle more on the white side and Anubis asks if she knew what saving Jack would cost her. Without saying anything, she realizes that sacrificing herself was enough to get her into heaven and Anubis tells her to say hi to her daughter for him (aw, he is a good guy after all).

Back in Heaven, Castiel is getting ready to leave as he is approached by Naomi. She thanks Castiel for saving them and offers him a reward; Michael’s location.
The episode ends with the team reunited again. They happily eat in silence until Jack asks if anything is wrong. Dean assures him everything is fine, especially since they now know where Michael is. Castiel reminds him that they don’t know where Dark Kaia or the Spear are, but Sam assures them that they will. Dean gets in his last word about how Michael will finally pay and they all toast together again.

Where do I even start to analyze this beautiful episode? It was, hands down, my favorite of the season and definitely in my top 20 of all time. I can’t help but get a sense that the series is setting up their end game knowing they can’t go on forever. With Castiel’s impending exit and the brothers barreling headfirst into a confrontation with Michael, we are heading into a world of pain. However, I love the fact that we can enjoy the here and now; especially with the episode ending on such a high point.