Spider-Man might be Marvel's most wholesome hero, and that makes him the target for some of the most despicable villains. Indeed, Spidey has a collection of enemies so vile that they rank as some of Marvel's most loathsome creations, from Green Goblin to Kraven the Hunter and everything in between.
However, not all of the Friendly Neighborhood's enemies are entirely irredeemable. In fact, some can be somewhat sympathetic given the right circumstances. Whether they are victims of a tragic fate or criminals trying to earn redemption, these bad guys might not be so bad after all.
Monster
Monster is one of Spider-Man's least-known villains. Carlie Cooper was one of Peter Parker's many love interests in the comics, but she broke up with him after discovering his superhero alter-ego. She ends up kidnapped by the Green Goblin, who infects her with the Goblin Formula.
Carly is the definition of a tragic villain. She doesn't choose to become evil and acts under Osborn's orders the entire time she's the Monster. Fortunately, her time as a villain is short-lived, but fans couldn't help but feel for her even when she committed crimes.
Shocker
Poor Shocker only seems to exist to be Spidey's punching bag; however, he actually seems to enjoy his status as a B-level villain. Shocker's inability to succeed makes him somewhat endearing to readers, and unlike other pushovers like Mysterio - who can be pretty odious--Shocker is sympathetic at times.
Shocker's attempts to become more powerful once led to him actually acquiring superhuman abilities, although they ended up putting his life at risk. It wouldn't be an overstatement to say Shocker is a bit of a joke when it comes to Spider-Man villains, which makes fans almost root for him whenever he manages to put the web-slinger in a tricky situation.
Kingpin
It takes a genuinely menacing villain to antagonize three different superheroes, but Kingpin somehow manages to do it. He is a threat to Spider-Man, Daredevil, and Punisher, a crime lord who can easily bring New York to its knees. However, there's more to Kingpin than meets the eye.
Several stories shine a light on what it's like to be Wilson Fisk. He is a family man at heart and even tried to leave his criminal life behind him at one point. However, his son betrayed him and tried to destroy his empire, and his wife, Vanessa, was seemingly killed before his eyes. Kingpin is a bad guy to the tee, but fans can still feel for him, considering the tragedies he endured.
Morbius The Living Vampire
Comic book fans know Michael Morbius as a former Nobel Prize-winning biochemist who gained vampiric abilities after a biochemical procedure failed to cure his rare blood disease. Cursed with an insatiable thirst for blood and a hideous appearance, Morbius briefly embraced his vampirism, earning an enemy out of Spider-Man.
However, Morbius has since evolved into a tragic figure, doomed to suffer from a condition from which there's seemingly no cure. Despite his savage instincts, Morbius is a victim of fate. He displays his willingness to lead an everyday life numerous times and even signs the Superhuman Registration Act during Civil War.
Sandman
Flint Marko started as another villain for Spider-Man, but gradually earned redemption and became an anti-hero. His powers resulted from an accident, and another bizarre situation merges him with Hydro-Man to form the monstrous creature known as Mud-Thing.
The time he spends trapped with Hydro-Man makes Flint question his choices, and he begins a path towards redemption. The road is tricky because he can't seem to shake off his former criminal lifestyle. However, he has occasionally teamed up with Spider-Man and even became a reserve member of the Avengers for a while.
Black Cat
Friend, foe, and occasional love interest, Black Cat can be anything she wants. She had a passionate affair with Spider-Man while he was separated from Mary Jane, thus forming one of the most famous love triangles in Marvel comic book history. However, the romance ended when Felicia made it clear she was only interested in Spider-Man and not Peter Parker.
The Black Cat acted as an anti-heroine throughout the years, pursuing her agenda while occasionally helping the web-slinger. Still, and even though she often goes back to her criminal ways, fans can't help but sympathize with her, especially whenever she's helping Spidey.
Harry Osborn
Peter Parker's best friend turned worst enemy, Harry Osborn, has one of the most tragic stories in comic books. Suffering from a distant father who, unbeknownst to him, is also a supervillain drives Harry to drugs, becoming self-destructive. His addiction pushes everyone away, including his girlfriend at the time, Mary Jane Watson. After he witnesses his father's death, Harry becomes mentally unbalanced and assumes the Green Goblin identity.
Fans could argue that Harry was but a victim of circumstance. The character shares plenty of sweet moments with Peter and even has a son, Normie, making him an easy target for the reader's sympathy. He dies and returns to life, dancing between the light and the dark, but both fans and Spider-Man himself will always have a soft spot for Harry.
Venom
Venom is one of those characters that became a hero because he was too popular to stay a villain. Still, Eddie Brock began as a pretty straightforward villain, consumed by his intense hatred for Spider-Man. Many fans consider Venom as Spider-Man's archenemy, alongside Green Goblin and Doctor Octopus.
Still, over time, the symbiote became increasingly heroic. Venom remained dangerously violent, but his plans shifted to the point where he actively avoided coming into conflict with Spider-Man. Venom is now a fan-favorite character, and fans can forgive many of his flaws because he's so entertaining, even if he maintains his killer instinct.
Doctor Octopus
Otto Octavius remained one of Spider-Man's most infamous and dangerous villains for years, with no chance for redemption. Indeed, some of Doc Ock's best storylines from the comics showcase his evil genius, cementing him as Spider-Man's ultimate archenemy.
However, things changed over time. Octavius and Spider-Man develop a complex relationship that leads to the former saving the latter, resulting in his death. Octavius returns years later, at one point inhabiting Peter Parker's body before transferring his consciousness to a Proto-clone. Octavius' story is everything but boring, and that's what keeps fans invested. He is unlike any other villain in Spider-Man's rogues' gallery, and his layered characterization makes it easy for fans to sympathize with him.
Lizard
In the pantheon of tragic comic book villains, few hold a candle to Curtis Connors. After experimenting with lizard DNA to try and re-grow his missing arm, Connors transforms into a feral lizard. Even after Spider-Man seemingly undoes the experiment, the Lizard keeps coming back, taking over Connors' mind in times of stress or despair.
Many of Connors' storylines center on his fear of one day losing control of his mind and body to the Lizard. His life becomes a living hell, and he becomes obsessed with finding a cure, neglecting his wife and son. Connors is Spider-Man's saddest villain, a man who became a victim of fate. The Lizard occasionally allies with Spider-Man, making him more popular among the fans already invested in his struggle.