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(#1) Sam Wilson (Falcon)
Not only is Falcon Captain America's best friend (next to Bucky), he spent a spell wearing the red, white, and blue as Cap. But he actually got his powers working alongside Red Skull. Before he turned good he was a petty Harlem thug and Red Skull henchman, then on getting his powers quickly turned on Skull and teamed up with Cap. They've been bros ever since. -
(#2) Hawkeye
Hawkeye's first encounter with the Avengers was.. robbing them. That's right, one of the most iconic Avengers was a petty thief. They soon saw his talent and convinced him to join them. The Avengers indirectly nodded to his history by having Loki brainwash him into supervillainous shenanigans throughout most of the film.
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(#3) Rogue
Rogue initially started out as an Avengers villain. She even took out Captain America! If you think about her powerset, it totally makes sense that she'd square off against Earth's Mightiest Heroes. Still, she's far more interesting as a tortured hero, which her decades with the X-Men have proven.
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(#5) Gambit
Gambit is one of those heroes that always seems to be up to something. That's because he started as a villain, albeit a charming man-about-town thief of a villain. It was later revealed he was partially responsible for the massacre of the Morlocks. He's made up for as a member of Xavier's crew, though.
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(#6) Venom
Venom started as a villain specifically out to get Spider-Man. Eddie Brock knew all Spidey's secrets, had all his abilities, and firmly believed that Peter Parker was responsible for everything that had gone wrong in his life. Eventually, he came to see that Spidey was just trying to make the world better, and he even fought alongside his former enemy. Nowadays venom is on Flash Thompson and is a full fledged government issued hero. -
(#8) Black Widow
Black Widow often references her dark past, and she isn't kidding around. Clair Voyant, the first Widow, was an anti-hero who killed evildoers and sends their souls to the devil. Natasha Romanoff, the current and more popular Widow, began as a Soviet spy and while she often played both sides, she also represented a very specifically Cold War image of nefarious, hyper-capable Russian femmes fatales.
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(#11) Emma Frost
She may help lead the X-Men now, but for years she helped lead another more nefarious group of mutants, the Hellfire Club. Forst was responsible for a whole lot of problems in the X-Men's formative years, making her a fascinating choice to teach at Xavier's School for Gifted Youngsters. -
(#12) Plastic Man
Plastic Man began as a low-level crook. He was an orphan who quickly fell into a life of crime. He lived as a thief for a short time after gaining his powers, but quickly realized he should use his elasticity for the benefit of all mankind. For a time he was a double agent, using his connections to the underworld to catch bad guys as his alter ego. -
(#17) Bombshell
She's a tricky one to pin down. She began as a member of the Teen Titans, and then in issue #40, she was revealed as a traitor. After being kicked off the team, she reformed and often teams up with Batgirl. So she's a villain disguised as a hero who turned into a real hero. -
(#18) Morbius, the Living Vampire
Morbius is a vampire. That in itself puts him at a slight disadvantage in the heroism department. He began as most vampires do, feeding on people. But then he began to specify only bad folks, then was able to synthesize a serum and lay off the human consumption altogether, so from there, it was only a short jump to using his powers for good. -
(#19) Prowler
Nowadays Prowler is Spidey's sidekick and occasional stand-in in the Marvel Universe, allowing Spider-Man to be seen alongside Peter Parker and throw people off the trail. But he started as a burglar using his tech knowledge to steal whatever he could. He was one of Spidey's foes for years before ultimately straightening himself out.
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