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"To love and win is the best thing. To love and lose, the next best."
— William Makepeace Thackeray (Quoted by narrator)
Phantom Blood was the one that started the journey of the Joestars, filled with laughs, frights, love and thrills... and so many tears.
- Even if Dio is unforgivably evil person from birth, it's still apparent that he cared deeply enough for his mother that he never forgave Dario when he beat her up, worked her to death, and sold her dress for booze. It's evident from his Manly Tears from his mother's dress- the last keepsake and his anger whenever Dario is brought up, that this love was genuine. It's heavily implied that she kept his sociopathic tendencies in check and had she lived, he wouldn't have turned out as monstrous as he did. It's a tragic aspect of the monstrous DIO that makes him initially relatable until he becomes a vampire.
- While he initially disregarded this love with his initial high as a vampire to have a mother eat her own child. His later decision to have children with multiple women while not personally raising them- was partially inspired by his own past and his mother's influence into wanting his children to have happier lives that he didn't and not be potentially abusive to them, much like Dario was to him. Possibly.
- The death of Jonathan's dog, Danny, is particularly crushing because the animal was the closest thing Jonathan had to a friend, and it's even sadder because of how easily it could have been prevented. The dog died only because Dio lost against Jonathan in a fair fight, and he got him killed in the cruelest way possible. note The first truly saddening moment in the series underscores just how much of a bastard Dio is.
- The rugby match that Jonathan and Dio had won. They both act like they've gotten over their rivalry and truly became brothers. Dio of course internally mocks Jonathan. Jonathan can't even imagine that Dio could be anything but the monster he was and still is from their childhood... and he feels horribly guilty for being suspicious despite the fact that he's right to.
- At the beginning of the Genre Shift, George Joestar protects Jonathan from Dio's dagger, and then dies in his arms. This is after making a speech on how he was sorry he was so hard on him since his youth.
- Bruford's tragic backstory, as well as his inevitable fate: Both he and Tarkus sacrificed themselves in order to save their master, Queen Mary, but it doesn't end well since Elizabeth, her political rival had already had her killed. With the revelation of their Senseless Sacrifice, it's little wonder why both he and especially Tarkus lost faith in humanity and became easy for Dio to control.
- The death of Will Zeppeli. He knew he was inevitably going to die the way he did, so he used it to Jonathan's advantage.
- The death of Jonathan Joestar: he dies to save Erina, his beloved wife and childhood sweetheart, an infant of a woman killed by a zombie to which he had no connections to, and his unborn child, on his honeymoon no less, taking Dio down to the bottom of the sea with him. Made all the sadder by the smile on his face when he dies, directed at his wife, the readers, and Dio himself.
- If one is somehow unaware of this plot point, they’d be forgiven in assuming Jonathan would find his way out of this in the end, like a usual Shōnen protagonist. After all, Jonathan has already faced quite a few near death scenarios and managed to come out on top. Nope.
- There's also the fact that in the end, even after all the damage Dio did, Jonathan was able to forgive him and call their relationship a "bizarre friendship". He even felt sorrow for when he thought he was dead after finally beating him. Talk about Too Good for This Sinful Earth. His final thoughts sum this up well:"Dio... as you observed, it may be true that our fate is to be together. I feel an odd warmth for you. For now, our lives are interwoven completely... and will end, along with this ship."
- And then his last words to Erina are even more heart-wrenching:"Farewell... to you... my beloved..."
- Somehow, even Dio makes the scene more sorrowful. He rants about his situation, about the ludicrousness of Jonathan's suicidal strategy, all while his head is cradled in his arms... and then he realizes that Jonathan has just died. The look of shock and then sadness on his face proves that as much as Dio loved boasting how his vampirism put him above normal humans, in these last moments he was as human as any man, and just lost someone who he considered his only equal.
- Made even sadder in the manga where Dio looks like he’s about to cry when he realizes Jonathan is dead.
- Note how Jonathan doesn't just Go Out with a Smile, he can only stare towards the distance, with light gleaming in his eyes, until he finally slumps over. He doesn't even stare at Dio as the latter is begging for the former to give him his body. Despite all the zombie rampages that just happened on his wedding boat, the prospect of bleeding out due to Dio's lasers fatally striking him in the neck, and his wife being caught up in all of this carnage, that shot of his glare showed that he always saw the good in everything, even doing that until his life completely faded away.
- What is especially tragic is how partially empty the sacrifice was given that DIO returns more powerful a century later than ever with Jonathan's body being desecrated and decapitated with DIO using it to commit more acts of evil. Thankfully, his descendants manage to defeat him finally.
- And even if his descendants managed to finally kill DIO, the vampire's backup plan ended up causing the deaths of the main lineage as well as the original universe.
- An underlying tragedy of the part is that unlike future main villains, who are strangers that the Joestars have to overcome with no personal connection outside of hate towards them, Dio and Jonathan grew up together with the former being an adopted brother. In spite of Jonathan's attempts to befriend him, their natures makes it impossible for them to truly get along. Even so, Jonathan did have selfless love for him, which on some level, Dio knew as well.
