Bobby's Flask
After Bobby's death, Dean found the flask in one of Bobby's duffel bags. Still grieving, he kept the flask, unaware that it was an anchor for Bobby's soul.
The flask is a 6oz pewter hip flask with a celtic design from the English Pewter Company,[1] with a tan leather pouch.
Episodes
7.11 Adventures in Babysitting
When one of Bobby's cell phones rings in his duffel bag, Sam opens the duffel bag to find the phone. As Sam answers the phone, Dean peeks into the duffel bag and takes out a flask which he sniffs before putting the lid back on.
7.12 Time After Time
Dean clearly keeps the flask close as it travels back in time with him to 1944. At first, it's confiscated and sits on the table between Dean and the police officer interrogating him. Later, we see Dean slip it into the inner pocket of his suit jacket after getting a fashion makeover to help him fit in.
7.13 The Slice Girls
When Dean wakes up in the passenger seat of the Buick Riviera Sam is driving, the first thing he does is reach into his inner pocket for the flask. As he takes a sip, Sam comments that he's surprised Dean kept Bobby's flask. Dean responds that the reason he did was that his "sprung a leak". Sam teases him, telling him most people would just carry around a photo as a memento, but Dean defends himself by telling him that this is his way of honoring Bobby, and he sees it as "grief therapy".
After going to The Cobalt Room bar and going home with Lydia, Dean goes to investigate a crime scene the next morning. Whilst there, he realises he's left Bobby's flask at Lydia's place. He calls Lydia to ask if she's seen the flask — which he describes as having "sentimental value". Lydia is standoffish and says she hasn't seen it, but will call if she comes across it.
Desperate to be reunited with the flask, Dean turns up at Lydia's house unannounced a few hours later. Lydia tells him she found it and that it was "so beat-up and old" that she almost threw it out. Dean remarks, "Yeah, well, guy it belonged to was beat-up and old too." He adds that he was close to Bobby and that he'd hate to lose it. Lydia then retrieves it from the top drawer of a dresser and gives it back to Dean who slips it into the inner pocket of his suit jacket.
Later in the episode, Dean takes the flask out of his back pocket and takes a swig multiple times as he and Sam research Amazons through Bobby's files. When some papers move on their own, revealing a helpful document, Dean suggests that it might be Bobby by waving the flask. Sam shuts the suggestion down, reminding Dean that they'd given Bobby a hunter's funeral.
7.18 Party On, Garth
In Garth's motel room, Sam and Dean do some research to figure out what invisible, clawed monster is killing members of the McAnn family. Dean is sitting on a couch, searching John's journal for clues when he picks the flask up from the end table beside him before taking a sip out of it. He then gets to his feet, still carrying the flask, and sets it down on the table where Garth is repairing his EMF reader as Dean reaches into the fridge to grab a beer. The EMF reader begins to warble, which is only noticed briefly by Garth.
Later, whilst Dean and Garth are driving to the McAnn residence after hearing a call for help on their scanner, Dean takes a swig from the flask again. Garth asks, "What's with the grody flask anyway? Lucky charm?". When Dean responds that it used to belong to Bobby, Garth remembers earlier how the flask set off his EMF reader. He asks Dean if it's possible that Bobby is a ghost and following them around. Dean tells him that they gave Bobby a hunter's funeral, but Garth points out an example of his cousin getting stuck after a hunter's funeral and also the fact that there are ghosts in India — where cremation is the norm.
Back at the motel, Dean refills Bobby's flask with more whiskey. He sets it on the table afterwards, and Garth accidentally turns Dean's EMF reader on and it begins to warble again. This leads to Sam admitting that he had already tried to contact Bobby with a talking board to no avail.
As they're leaving the motel, Dean gets into the car and realises he's forgotten the flask. He quickly goes back to retrieve it from the motel room saying, "There you are", unable to see the ghost of Bobby standing in the middle of the room.
7.19 Of Grave Importance
Whilst he and Sam are waiting for Annie Hawkins at the Pier Front restaurant in Bodega Bay, California, Dean pours some whiskey from the flask into his cup of coffee and says, "Here's to ghosts that aren't there." Sam notes that Dean sounds disappointed that — they think — Bobby's ghost isn't following them around. Dean admits that although he wishes he could see him again, it doesn't mean that they should. After he lays the flask down on the table, it begins to move, unnoticed by Sam or Dean.
When they leave the restaurant, Dean takes the flask from his pocket and prepares to take a swig before realising it's empty. He comments that he needs a refill, and Sam suggests he put the flask away since all it does is remind them of Bobby. Dean says he's thought about it, but he's not ready to part with it yet and he tucks it back into his pocket.
Later, Sam and Dean leave Annie's motel room to go investigate the Van Ness House and Dean momentarily leaves his jacket behind — along with the flask in its pocket — much to the dismay of the ghost of Bobby who is anchored to the flask. Thankfully, Dean remembers at the last minute and quickly retrieves his jacket from the motel room.
As Bobby and Annie are investigating the Van Ness house, Bobby suddenly vanishes and reappears in the car with Sam and Dean because Dean had left the building with the flask. Dean takes a sip from the flask, unaware of Bobby's ghost in the backseat.
Back at the motel, Bobby finally manages to communicate with Sam and Dean via a steamy mirror — telling them that Annie's spirit is stuck in the Van Ness house. At first, Dean is confused as to why Bobby is there. However, Sam quickly figures out that it's because of the flask.
Sam and Dean return to the Van Ness house to try and find Annie. By now, Bobby has learned how to lift physical items in his incorporeal state, and he takes the flask from Dean's pocket and places it in a drawer.
After they defeat Whitman Van Ness and the boys can physically see Bobby's ghost now, he returns the flask to Dean. They then give Annie a hunter's funeral and Dean raises a toast to her with the flask. Dean admonishes Bobby for choosing to stay on earth as a ghost and Bobby gets irritated, disappearing. Dean throws the flask into the trunk of the car and closes it.
7.20 The Girl with the Dungeons and Dragons Tattoo
As Sam and Dean are at Rufus' cabin trying to figure out what Dick Roman is funding archaeological digs for, Dean sits down on the arm of a couch and takes a sip from Bobby's flask. Right after, the lights begin to flicker. The boys are instantly on-guard, getting up and drawing their guns. Fortunately, it's just Bobby's ghost appearing behind them.
After they get an automated email from Frank — from beyond the grave — telling them that someone is trying to hack his hard-drive, they use the GPS Frank connected to it to locate it to Richard Roman Enterprises corporate headquarters in Chicago, Illinois. Bobby suggests mailing the flask to the building so he can investigate it without putting Sam and Dean at risk by having them break in. However, Sam and Dean don't think it's a good idea given the risk that Bobby may become a vengeful spirit if he runs into Dick.
When Sam, Dean, and Charlie begin to execute their plan to break into Dick's office and hack into his email account, Sam and Dean watch Charlie through security cameras. Dean notices Bobby's flask in Charlie's bag and realises that Bobby slid it in there without them noticing in order to get inside the RRE headquarters. Dean quickly calls her on her bluetooth headset and tells her to check her side-pocket of her bag. Charlie takes the flask out and takes a sip, thanking Dean. Dean goes on to tell her to be careful with it — that it's a "family heirloom" and a "good-luck charm" — and not to lose it.
Once she copies the data from Dick Roman's PC to a flash drive and makes it back to her desk, Charlie takes another swig from the flask. Later in the episode, Bobby is able to help Charlie escape from RRE headquarters by smashing the windows when the building goes on lockdown, and throwing Dick around to slow him down.
Charlie gets her broken arm checked out at a local hospital before saying farewell to the Winchesters, telling Dean she left the flask on the backseat of the car.
7.22 There Will Be Blood
After Bobby has an angry outburst at Dean in the bathroom of Rufus's cabin, and whilst Sam and Dean are on their way to find the Alpha Vampire to acquire his blood for a spell to kill the leviathans, Sam gives Dean a non-verbal cue to put the flask in the backseat of the car so that they can walk off and remain unheard by Bobby's ghost. Dean takes the flask out of the pocket of his new jacket and places it in the backseat of the car. As they shop for snacks in the Gas-N-Sip, Sam and Dean discuss Bobby's deterioration and what to do if he becomes a vengeful spirit.
When they get to Missoula — where the Alpha vampire is laying low — Sam and Dean check into a motel and leave Emily there. Dean locks the flask away in a safe to ensure that Bobby stays behind so as not to get him involved in any fighting.
Unfortunately, Bobby figures out the combination on the safe — his birthday — and possesses the motel maid in order to unlock the safe and take the flask. With the flask in hand, Bobby is able to leave the room in search of Dick.
7.23 Survival of the Fittest
After Bobby attacks Sam at the SucroCorp headquarters, he manages to snap himself out of his rage just in time and leaves Louise's body. The next day, back at the cabin, Dean is staring at the flask which is lying on a coffee table, deep in thought.
Bobby's ghost pops up later and expresses guilt for almost killing Sam, but admits he's close to going vengeful. He tells them to burn his flask and gives them some advice — not to stick around when they die. Respecting Bobby's wishes, Dean places the flask (minus the leather pouch) on top of hot coals in the basement of the cabin and Bobby's ghost disappears in flames, his spirit laid to rest.
8.06 Southern Comfort
When salting and burning a spectre's bones doesn't stop its rampage, Sam suggests that something might've been stolen from the tomb and that the spectre's spirit has clung onto it. Dean agrees, citing Bobby's flask as another example of a spirit latching onto a physical object.
11.16 Safe House
In 2009, Bobby is helping Rufus with a suspected ghost case. After digging most of the grave with a digger vehicle, Bobby hands Rufus a shovel and tells him it's his turn. As Bobby takes a break and sits on the edge of the grave, he takes a sip from his flask.
