Taxi Driver

Taxi Driver is the 19th episode of Season 8.

Summary
Sam and Dean respond to a call from Kevin, who is terrified after hearing Crowley's voice in his head. After hearing Kevin's news, Sam and Dean team up with reaper named Ajay (guest star Assaf Cohen), who helps them deal with the second trial from the Tablet. Meanwhile, Dean receives a visit from Naomi and realizes he must find Benny and ask for a huge favor.

Plot
Slowly unraveling, Kevin Tran begins to hear the voice of Crowley in his own head, taunting him and presenting him with demonic visions. Later, the Winchesters arrive in response to his SOS, but deny that Crowley could somehow be in his head. In any case, Kevin presents Sam and Dean with word that he’s translated the second trial, that they’ll have to venture into Hell to ferry a soul up to Heaven.

Torturing a Crossroads Demon, Sam and Dean learn that certain “rogue” reapers act as Coyotes to take people in and out of Heaven and Hell, one of which agrees to take them for a price. The reaper identifies himself as the one who took Bobby Singer’s soul down to Hell, and Sam immediately volunteers to take the trip, leaving Dean behind. Dean reluctantly agrees to let Sam go, while the reaper Ajay opens a magical doorway in nearby alley, watched by a mysterious stranger.

Sam and Ajay first arrive in Purgatory, the man’s secret route into Hell, but Ajay insists Sam must travel alone and find a specific rock formation that will take him to Hell, returning in exactly 24 hours. Sam immediately finds himself faced with several monsters, while back on Earth Dean returns to find Kevin Tran increasingly paranoid and sleep-deprived. Though Kevin wants only to quit the life, Dean assures him men like them shoulder more weight then most, but find a way to power through. Meanwhile, Crowley intimidates the reaper Ajay into admitting he took Sam to Purgatory for uncertain reasons, before Crowley kills him.

Sam finally unearths the portal to Hell and ventures inside, finding a glowing dungeon full of mutilated victims crying out for his help. Finally, Sam happens upon Bobby’s cell and opens the gate, but the deceased hunter immediately punches him to the ground, believing him another of Crowley’s hallucinations. Meanwhile in Crowley’s office, the demon wonders what Sam and Dean could be up to, before tasking a subordinate with finding Kevin Tran.

Cooking breakfast, Dean finds that Kevin acted rashly and decided to hide the demon tablet as a preemptive measure, keeping its location from even Dean. Naomi (Amanda Tapping) suddenly appears before Dean, appealing to him that they’re on the same side with regard to Castiel and closing the gates of Hell, before revealing that Ajay’s way into Hell involved taking Sam through Purgatory first. Meanwhile down in Hell, Sam and Bobby fight their way out off the dungeon, and venture outside into the adjacent Purgatory.

Dean returns to Ajay’s taxi to find the demon deceased, and makes a desperate move calling Benny for a favor to ask. Meanwhile down in Purgatory, Bobby and Sam catch up on the trials, Bobby assuring he’d love to return to Earth should Sam and Dean find a way, when Sam realizes that Ajay hasn’t shown up at the rendezvous point.

Meeting with Benny in the alley, Dean worries that he’s asked Benny too big a favor by asking him to rescue Sam from Purgatory, but Benny admits he hasn’t been able to fit in on Earth as well as he’d hoped. Dean graciously thanks his friend for the sacrifice, and urges Benny to ride Sam out of Purgatory as he had before, before beheading the vampire. Back down in Purgatory, Bobby balks at the idea that Sam let Dean remain in Purgatory for a year, before several monsters appear. Benny arrives in the nick of time to fight them off, as both Bobby and Sam express unease at taking help from the vampire.

Shortly thereafter, Benny leads Sam and Bobby to the portal out of Purgatory, and Sam performs the ritual to place Bobby’s soul in his body. True to his word, Sam offers the same to Benny, but when several vampire associates of Benny appear, Benny urges Sam to give his regards to Dean as he attacks the creatures, allowing enough time to finally escape.

In the Maine wilderness, Dean finds Sam emerging from the portal, but becomes distressed that Benny didn’t attempt to return with Sam. The brothers perform the ritual to release Bobby’s soul from Sam’s body, but soon find the soul’s ascension blocked by Crowley. Crowley refuses to release the soul, but Naomi soon appears and threatens him into fleeing, assuring Dean they’re on the same side after all. Left alone in the wilderness, Sam performs the spell to confirm his completion of the trial, which once again forces him to double over in pain.

Still hearing Crowley’s voice, Kevin cowers as the glass from the boat shatters, finally allowing Crowley entry to the sanctuary. Crowley reveals that he killed Kevin’s mother, before using her phone to find his location, and the last we hear of Kevin are his screams from inside the boat. Sometime later, after agreeing that Benny was a good man after all, Sam and Dean return to Kevin’s boat to find he and his research gone, believing him to have fled on his own.

Characters

 * Dean Winchester
 * Sam Winchester
 * Kevin Tran
 * Crowley
 * Naomi
 * Benny Lafitte
 * Bobby Singer