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Welcome to Part 3 of our (spoiler free!) photographic examination of Supernatural’s beloved character, Bobby Singer (to catch up on Bobby’s story, start with Part 1: Creating Bobby’s Character). To recap what has been covered so far, Bobby’s character was introduced to the Supernatural series at the end of its first season. Season 2 developed Bobby’s roles as a father figure to the Winchester brothers, an experienced hunter, and a researcher for supernatural and mythological creatures. Seasons 3 and 4 then expanded Bobby’s character by providing more of his personal history, his history with the Winchester family and his history as a hunter. By the end of the first four seasons, Bobby was a cornerstone of the Supernatural story! This conclusion looks at how seasons 5-8 enriched, changed and expanded Bobby’s story in ways that were sometimes wonderful and sometimes shocking, but always interesting!

Enjoy! – Nightsky


7.06 “Slash Fiction” – Bobby’s roles expanded, literally and figuratively!

Bobby Presence in the Story

The first four seasons of Supernatural celebrated a resourceful, sarcastic, wise old hunter named Bobby Singer. Bobby’s character, masterfully portrayed by Jim Beaver, quickly evolved into one of the most loved characters of the series. Surprisingly, Bobby only appeared in 20 episodes in these early years (approximately one third of the 67 episodes that aired after he was introduced). Acknowledging the inner-geek that analyses the dynamics of a character’s development (sorry, this will only take a minute…), Bobby’s character was concentrated in the “bookends” of each season, i.e. the opening and closing episodes. Surprisingly, he was only seen two or three times in the middle of each season!


As a testament to Jim’s talent, Bobby’s value to the story and his popularity with the fans steadily grew, until he was used in half of the episodes in seasons 5, 6 and 7! 

Number of Appearances Each Season:


Even though the number of Bobby’s episodes increased as the show’s story matured, the pattern of when he appeared remained the same, i.e. heavily at the beginning and end of each season, and sporadically in the middle.


Dialog references (e.g. “I just spoke with Bobby”) and one-sided phone conversations were frequently used to make it seem like Bobby was always involved in the storyline, but Jim, in fact, remained a “guest star” on the series. (Okay, geeky analytics concluded. Sorry, I found that interesting…)

Evolving Traits in Bobby’s Character

In the first few years of the show, Bobby was meticulously depicted as a father figure to the brothers, an extraordinary researcher of lore and an accomplished hunter. Seasons 3 and 4 had also carefully introduced vulnerability, human flaws and a complicated past into Bobby’s character. The series’ later seasons continued to develop these roles and character traits, bringing some of them to their ultimate conclusion: 

Father Figure

In the very first episode of season 5, Bobby’s love for “his boys” was used to set up one of the most poignant scenes of the series.  Possessed by a demon and ordered to kill Dean, Bobby’s love enabled him to overthrow the demon’s control and stab himself rather than harm Dean.  Bobby’s choice and willpower precipitated one of the most significant changes in his character (discussed later) and more importantly, foreshadowed the season’s gut-wrenching climax.


5.01 “Sympathy for the Devil” - Out of love for Dean, Bobby seriously wounds himself rather than hurt Dean 

Also in this episode, Bobby reaffirmed his love for Sam, assuring him, “I ain’t cutting you out, boy. Not ever.”  Bobby again risked his life and endured great pain to save both of his boys in “Frontierland” (6.18), when he allowed Castiel to tap into his soul to bring Sam and Dean back from the past.  So there could be no doubt as to his dedication to the brothers.

While the early seasons implied and developed a fatherly connection between Bobby and the brothers, the later seasons evolved the relationship into a more comfortable, accepted and adoptive family bond. In “Appointment in Samarra” (6.11), Sam used Bobby in a spell that required paternal blood, signifying that Bobby now filled the fatherly role fully and completely for Sam.   In “Death’s Door” (7.10), Bobby returned the sentiment, telling his reaper “they’re my boys!”.  Earlier expressions of love had always been “like family” or ‘like a father” (e.g. in “Dream a Little Dream of Me” Dean told Bobby “I’m not gonna let you die. You’re like a father to me.”). In the emotional exposition of “Death’s Door”, though, Bobby said he saved his best memory for last - a memory of “his boys” teasing each other. From the moment Sam and Dean reappeared on his doorstep, these three people had endured apocalyptic hardships, emotional losses and triumphs that strengthened their bonds into a true family. 

Researcher and Hunter

By the beginning of season 5, Bobby’s formidable skills as a researcher had “saved the day” so many times his knowledge was now an indispensable component of almost every hunt. In “Abandon All Hope” (5.10), Bobby deciphered clues and determined that raising Death, the horseman, was the cause of the town’s demon activity. In season 6, Bobby taught the boys about Skinwalkers, dragons and the Mother of All, Eve. Since Bobby had extensive skills as both a researcher and a hunter, though, his assistance often now alternated between providing “behind the scenes” help and joining the team in the field.  Late in season 5, Bobby committed everything he had to the cause when he followed in Dean’s footsteps and sold his soul, in his case to gain critical information to avert the apocalypse (i.e. the location of the last horseman). He was on the team that attacked the warehouse where the Croatoan virus was stored and he later fulfilled his “all in” commitment by sacrificing his life in a vain attempt to stop Lucifer with a bullet. Seasons 6 and 7 included him fighting Khan Worms, Eve, Crowley, vampires and ominously, Leviathans. He was never portrayed as a fifth-wheel or a hunter past his prime. On the contrary, he was respected and always equally contributed to or in some cases surpassed Sam and Dean (they were pretty impressed when he shot a zombie out of a tree by aiming at the sound!). His vast hunter network also continued to add to the story, significantly introducing the boys to Frank Devereux. Bobby’s research and hunting prowess grew in importance and significance to the story, culminating in the ultimate categorization from Sam in “The Slice Girls” (7.13) as a “crazy, drunk, old genius”. Quite a compliment for a character that initially appeared to be a recluse buried in the dust of a lot of old books!

Vulnerable Bobby

Season 5 continued to explore the vulnerability that had been introduced into Bobby’s character in the prior two seasons.  Almost as a reminder of Bobby’s helplessness in “Dream a Little Dream of Me”, season five’s first episode “Sympathy for the Devil” put Bobby back into a hospital bed, this time immobile from physical vs. mental injuries. The parallel images connected the two timelines.


5.01 “Sympathy for the Devil” - Bobby back in hospital after stabbing himself

The next time we saw Bobby, he had been transformed into the “injured warrior”, confined to a wheel chair from his stabbing wound.


5.03 “Free to Be You and Me” – Bobby contemplating his new role as a hunter confined to a wheel chair

Bobby’s despondence and abrupt physical confinement diminished his image as untouchable and indestructible, and suggested the he might not always be the brothers’ emotional or physical refuge. Following through on this theme, Bobby’s depression triggered another degradation of his character only a few weeks later.  In “The Curious Case of Dean Winchester” (5.07) Bobby’s age was accelerated by 25 years, literally and symbolically compromising his strength even further. 


5.07 “The Curious Case of Dean Winchester” – Bobby aged 25 years, and was more vulnerable than ever before

In this episode, Bobby confessed that he had felt useless since being injured and had contemplated suicide because he couldn’t hunt anymore. To dramatize his limited accessibility, Bobby could only continually call Dean’s name as Dean lay dying of a heart attack in the adjacent high rise apartment. Dean’s response at the end of the episode reestablished Bobby’s role in the hunt, though:


Dean: “…You’re not useless, Bobby.”

Bobby:   “Okay.  Good Talk.” 

Dean:   “No, wait a minute. Listen to me.  You don’t stop being a soldier ‘cause you got wounded in battle. Okay? No matter what shape you’re in, bottom line is, you’re family. I don’t know if you’ve noticed, but me and Sam, we don’t have much left. I can’t do this without you. I can’t.  So don’t you dare think about checking out. I don’t want to hear that again.”

Ironically, Bobby chastised Castiel for lamenting his “uselessness” in 5.21 with much the same speech that Dean gave Bobby (only shorter and a lot less empathetic!). Although Bobby regained the use of his legs at the end of season 5, the brothers had to learn how to survive with Bobby compromised. His frailty had been emphasized throughout the season, symbolically stripping him of his indestructibility and foreshadowing his ultimate downfall.  


# KELLY 2013-09-20 19:31
It was a lovely analysis. I quite like the geek statistic stuff personally. I loved Death's Door despite it being horribly sad. I did think they knew they were bringing him back as a ghost, but I don't think it was done extremely well.
# Kelebek 2013-09-20 23:25
Thanks, Nightsky, for this review. I really enjoy looking back at all seasons of SPN through other people's perspectives. I, like the rest of the fans, couldn't believe that they'd killed was great to see him back even if it was as a ghost! :-)
Maybe it's because I just finished watching 'the devil you know', that I have this one Bobby line in my head (said to Crowley):
"Well, then get the hell off my property before I blast you so full of rock salt, you crap margaritas."
It's not a photographic moment of Bobby per se, but I can't help but laugh every time I think about it.
leah unlogged
# leah unlogged 2013-09-21 11:58
This was a very fitting tribute to Bobby. I enjoyed all three parts. I will always miss him being a part of Sam and Dean's daily lives. I do admit to having mixed feelings about them bringing him back repeatedly. The farewell in Death's Door was sad and lovely. As much as I love Bobby/Jim I sorta wish they had left it at that. But I admit to looking forward to it when they say he's returning! Conflicted much?
# novi 2013-09-21 12:29
Too good an actor to lose him, too adorable a character, Bobby (and Jim) really became an integral part of the show so whenever they bring him back I will be greeting him with huge Welcome as I think everybody on set does.
# nightsky 2013-09-21 17:20
Kelly, Thank you for the feedback about the data tables! I created those as I was writing Part 1 and used them continuously while researching the rest of the story, so they were invaluable to me. I just wasn't sure if anyone else would find them interesting. I'm glad you liked them!
# nightsky 2013-09-21 17:26
Kelebek, I love that line too! The writers gave Bobby really witty quips. I think that is part of his charm. Actually, the next part of this series of articles will be all the wise things he said to the brothers. I have been writing them down as I remember them or see them on reruns, but I am still missing so many!
# nightsky 2013-09-21 17:46
Leah and Novi, I admit I am on the side of looking forward to having Bobby back. Jim commented that it was an interesting, new angle, so I am open to seeing what the writers have cooked up. It doesn't bother me that they keep bringing Bobby back. I like the character and the actor, and I think he is a healthy addition to the brothers' lives. I like that he isn't afraid to yell at them, support them, challenge them, etc. Frankly, for all the reasons stated in the article, I think the character has become so valuable to telling the story that his presence makes a few things easier for the writers (plot and character exposition, for example) and enriches the story. As much as I like Charlie and Kevin as supporting characters, neither one can compete with the 7 year history we have with Bobby. He is a non-controversi al, liked, easy character to write; the actor is available and easy to work with and has his own following that adds viewers to the show. Really, it's all up-side to use him.