The popularity of The Vampire Diaries hasn’t waned since it first aired in 2009, and fans are still greedy for the supernatural happenings in Mystic Falls, the heart-wrenching love triangle between Elena, Damon, and Stefan. The same goes for interspecies rivalries between vampires and werewolves.

Nina Dobrev, Ian Somerhalder, and Paul Wesley also reached the upper echelons of fame as the leads of the show in the 2010s, but if The Vampire Diaries was made in the ’90s, the casting of the main characters would have looked a lot different than it is now.

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Elena Gilbert/ Katherine Pierce: Winona Ryder

Elena’s character was a quintessentially sweet girl who was introspective and liked writing things in her journal, had a knack for attracting horror and mystery to herself, and could often be conflicted between what was good and bad for her.

Winona Ryder would be the perfect person to play her with her fair share of experience in supernatural Tim Burton movies like Edward Scissorhands and Beetlejuice, mystical suspense work like Dracula, and more. She is also known for roles where she writes or journals a lot, like Jo in Little Women, which is perfect because Elena can often be seen writing in her journal. Ryder was Hollywood’s sweetheart in the ’90s, and that title could fit Elena too.

Damon Salvatore: Ralph Fiennes

The antihero of The Vampire Diaries, Damon Salvatore could be funny, alluring, roguish, and cunning at the same time. Like Somerhalder, the character had to have a certain look in the eye and also pull off being scary and romantic at the same time.

A young Ralph Fiennes definitely fits the bill with his experience of playing a conflicted, flawed hero in Wuthering Heights as well as a villainous Nazi commandant Amon Goeth in Schindler’s List. Damon himself could be quite brutal when he fought and even in love, but also had a softer side which Elena could bring out of him. These two sides of Damon’s personality would be captured well by Fiennes as he can masterfully play both kinds of characters.

Stefan Salvatore: Paul Rudd

The better brother, Stefan was genuine, an actual nice guy, and someone who cared, unlike his brother Damon. Stefan and Damon both tussled over Elena, but Stefan was fairer and overall more likable.

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Paul Rudd would be a great fit to play Stefan in the ’90s. His good-natured personality as Josh in Clueless set him up nicely for Stefan’s character with noble traits. Rudd also played a high schooler in Overnight Delivery, which wasn’t a character quite like Stefan, but could be in love the way Stefan was. Rudd has the unique trait of playing characters who are innately good as well as conflicted ones, which is why he would be a great Stefan.

Bonnie Bennett: Halle Berry

The prescient and powerful Bonnie may be a teenager but could be wise beyond her years. A good friend to not only Elena but also Damon, she had the magic of the old witches in her and had no problem in flexing that muscle when it came to saving her friends or herself.

To recast her in the ’90s, it would be remiss to not pick Halle Berry, a certified icon and also a woman who would go on to play supernaturally omnipotent roles for X-Men as Storm. She has a knack for performing well when it comes to powerful women who can handle themselves, and Bonnie Bennett was one of the strongest characters on the show who wasn’t afraid to get angry when she had to.

Klaus Mikaelson: Leonardo DiCaprio

Klaus was one of TVD‘s best villains. He was an unpredictable character who could be extremely romantic when he wanted, and extremely dangerous as well. It all depended on what he was feeling, and Joseph Morgan balanced the many sides of his personality perfectly.

From the roster of ’90s heartthrobs, Leonardo DiCaprio has played enough romantic roles in Titanic and Romeo + Juliet. His cunning side could also be seen in Catch Me If You Can as the notorious conman Frank Abagnale. Klaus could be a romantic or ruthless, a dichotomy that DiCaprio with his acting prowess could nail.

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Alaric Saltzman: Samuel L. Jackson

The fatherly figure that was Alaric started off as a man who had the best interests of everyone, especially Elena and Jeremy, at heart, but his vengeance against the supernatural led him to become bitter and enraged, unfortunately.

Samuel L. Jackson is known for his tough and gritty roles. Action-packed Jungle Fever and Pulp Fiction set him up for roles where he uses weapons to hunt down people, which he could easily do in Alaric’s role for vampires. Jackson has the tough exterior of a hunter but can also perform the wisdom that Alaric imparted to Elena and Jeremy as a paternal figure to them.

Caroline Forbes: Sarah Michelle Gellar

Deadly yet friendly, Caroline Forbes was a human teenager who started off as a cheerleader with a mean streak, but got turned into a badass vampire who retained her humanity but now had a real edge over people.

Sarah Michelle Gellar is no stranger to teen horror, and while she may have been a vampire slayer in Buffy: The Vampire Slayer, she could have made for a great Caroline in The Vampire Diaries. As Buffy, she was girly but strong, with mannerisms that matched Caroline’s in TVD. Her roles in I Know What You Did Last Summer and Scream 2 also made her an obvious choice for another supernatural horror show for teenagers, where she could add her spunk to Forbes’ character.

Tyler Lockwood: Omar Epps

The jock-turned werewolf was a fan favorite. He could be a witty teenager at times, or a rage-filled wolf that could bring vampires down in seconds. Tyler was well appreciated for his character and looks too.

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Omar Epps is a thriving ’90s icon and teenage sporting and jock roles were his go-to — think Q in Juice, Malik Williams in Higher Learning, and Quincy in Love & Basketball. While Omar’s roles were a lot more serious in nature, he could adapt well to a teen drama and play a jock who needs to deal with becoming a werewolf like Tyler Lockwood.

Jeremy Gilbert: Edward Norton

Elena’s younger brother went through several transformations in The Vampire Diaries. The death of his parents left him low and disturbed, but hunting down baddies gave him a new lease on life and made him more confident and present.

Edward Norton is best known for his cult-favorite role in David Fincher’s Fight Club, where he too played a troubled young man who descends into a whole other persona and world to cope with the world, much like Jeremy. The innocence of Jeremy became an obsession and Norton can play that role to a tee.

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