Although Frodo is often seen as the more tragic character, Bilbo has his fair share of pain and sadness throughout his unnaturally long life. From his best (at least in the movies) friend dying in his arms to regretting the burden he places on his young nephew’s shoulders, Bilbo’s life, as depicted in both The Hobbit and The Lord of the Rings, hasn’t been the easiest or the happiest.
Seeing as how seeking thrills is a known Baggins-Took trait, it comes as no surprise that Bilbo had his own memorable adventure, but it also ends up bringing him a lot of pain and regret. Unfortunately, even though his naturally happy hobbit nature never actually allows him to dwell too much on it, his sadness still overtakes him from time to time.
He Is Misunderstood By His Fellow Hobbits
As Bilbo himself says, hobbits aren’t really fond of the whole adventure business, so his love for the unknown and the unexpected is understandably seen as weird and untrustworthy. Disturbing the peace, most often under the influence of Gandalf (who has been inspiring adventures since the Old Took was young), is not desirable at all, and few things are as disturbing to hobbits as Bilbo’s journey with the company.
Still, it appears that most of the Took (and Baggins) hobbits tend to be misunderstood by their peers, so it’s not surprising that Bilbo isn’t trusted either. He is, after all, known as Mad Baggins.
He Is Forced To Choose Between Life And Death
In what is perhaps the most consequential dilemma in both the movies and Tolkien’s original works, Bilbo decided to spare Gollum’s life in the goblin kingdom under the Misty Mountains. This act of mercy and kindness towards a wretched and desolate creature is ultimately defining for Bilbo’s story arch and the overall message of The Hobbit, but it is not an easy decision.
To be forced to choose between sparing the life of an objectively horrible being and killing it is not an easy task, as Bilbo is struck by the possibility of escaping the mountain but at the cost of his, for lack of a better word, humanity. His pity, mixed with horror at the idea of becoming a second Gollum, is what helps him choose in the end, yet it is a tough choice nonetheless.
His Only Heir Leaves Middle-Earth With Him
Seeing as how Bilbo never married or had children, his only true heir was his cousin/honorary nephew/adopted son Frodo. The boy is so similar to him that one might easily mistake them from father and son, considering how ready they both are for an adventure, and it’s only natural that Frodo would have been expected to continue the line.
In the end, however, Frodo’s own adventure catches up with him and he leaves the Shire for the second time, except it is for the Undying Lands, thereby severing Bilbo’s last chance of an heir.
He Is Underestimated By The Company
For a long time, the company doesn’t really see Bilbo as all that useful, although this is more apparent in the books than in the movies, where most of the mistrust comes from Thorin. Since Gandalf doesn’t dwell too much on Bilbo’s use as their burglar, and Bilbo himself often unintentionally hinders the quest by leading them into traps or simply not being able to keep up, it’s not that difficult to see why the dwarves might be a bit cold. After all, Bilbo’s growth into a skillful companion is a lot slower on paper, marking one of the many things about Bilbo that aren’t like the books.
Still, Bilbo ends up being arguably the most important player in their saga, albeit a very unassuming one, and the stiff attitude he had to suffer through throws a sad shade on his adventure.
He Has To Betray His Closest Friend
In the movies, Bilbo and Thorin have an especially close relationship, a lot closer than the one they have in the books. Bilbo’s desire to help Thorin and to stop him from starting a doomed war with the Mirkwood elves leads him to steal and give away the Arkenstone, a feat some might see as a betrayal (and Thorin certainly does).
Much of the anxiety and tension in the third movie of the trilogy centers around Thorin’s paranoid suspicions regarding his people, and he places his trust in Bilbo, and it is clear that the hobbit feels torn when he makes the decision to give the Arkenstone to Bard.
He Watches His Friends Die
Arguably one of the saddest points in the trilogy is the death of Fili and Kili. Although they die in the thick of battle in Tolkien’s books and their deaths are heroic and legendary, the circumstances around their movie deaths are far sadder, making them some of the most tragic characters from The Hobbit and LOTR. Fili is killed as a sacrificial lamb and as bait, Kili dies quickly but rather gruesomely. Nobody has the time to mourn them properly in the heat of the war.
Bilbo, alongside Thorin and the dwarves that chose to stop Azog, has to witness the grotesque death of Fili while being unable to do anything to stop it. Even the strongest person would crack after that.
He Spends His Life Alone
The fact that Bilbo stayed unmarried his whole life has been the subject of a lot of speculation in the fandom, but facts are facts. Both he and Frodo don’t seem to have any love interests, both in the books and in the movies. Of course, there is absolutely nothing wrong with this, but Bilbo doesn’t seem to have anyone truly close other than his adopted son/cousin/nephew, and he isn’t all that asocial otherwise.
Even though he does form some of the best friendships in LOTR, particularly with Gandalf, and there can be a number of reasons why he chose to remain alone, seeing him get to spend his admittedly long life happy with someone might have been a more satisfying story for some fans.
He Is A Ring-Bearer
Bilbo isn’t nearly as affected by LOTR and The Hobbit’s most iconic weapon, The One Ring, as Frodo and Smeagol. This is natural since he comes into possession of the Ring by exhibiting mercy and kindness. Furthermore, he lives far away from Mordor, and Sauron’s power is much less tangible in the Shire. The only visible effect the Ring has on Bilbo is the longevity it gifts him with.
However, as Gandalf prompts Bilbo to give up the Ring it becomes obvious that its hold is actually a lot stronger than it appears to be. This sort of desire isn’t explored from his point of view but judging by Tolkien’s hints, it does seem to be difficult to bear nonetheless.
He Goes To The Undying Lands As A Mortal
This is a particularly bittersweet moment for Bilbo’s character since being allowed to enter the lands of Aman is a privilege of the immortals that isn’t bestowed easily to the mortal children of Ilúvatar. As a ring-bearer and an Elf-friend, Bilbo is granted entry. However, he remains mortal even if he has the choice to live as long as he sees fit.
Receiving the opportunity to live among the immortal in eternal bliss while being mortal yourself is a double-edged sword since it would be quite easy to yearn for immortality when you are surrounded by it.
His Best Friend Dies In His Arms
This is more of a movie detail since the friendship of Bilbo and Thorin is explored in much more detail and appears to be a lot deeper in Jackson’s The Hobbit trilogy. Bilbo, who at this point doesn’t seem to have many friends, grows closer to the heir of Durin and appears to understand him on a deeper level than most, seeing the signs of dragon sickness much earlier than the rest of the company.
In one particular movie-only scene, the famous acorn scene, the close friendship of the two is cemented and makes the loss of Thorin that much more tragic. From breaking down alongside the king’s lifeless body to sobbing during his funeral, Bilbo’s reaction to Thorin’s death shows the true devastation he feels in the moment his closest friend dies. It is also the one major instance in the movies where fans see Bilbo truly sad, a harsh contrast to the happy hobbit everybody knows and loves.
