The Legacies, the franchise had 331 episodes, which meant that actors could easily find a role that they were well suited for, whether that meant serving as main characters, love interests, or guest stars. In addition to a line on their resume, The Vampire Diaries actors gained experience working with various props and effects to fit the supernatural setting, which was beneficial in their future careers.
Several Vampire Diaries guest stars found success in Hollywood, and many developed a love for supernatural and/or fantasy television series, which led them to one of the other biggest shows running at the time. Once Upon a Time aired from 2011 to 2018, and it featured characters from fairytales navigating the real world, which provided plenty of roles for actors who wanted to continue working with special effects, elaborate costumes, and expansive lore. Nine actors featured in both the Vampire Diaries franchise and Once Upon a Time, establishing themselves as experienced players in the fantasy television genre.
9 Amy Manson - The Dryad / Merida
As a Scottish actress, Amy Manson was an outlier in the Vampire Diaries to Once Upon a Time pipeline, as she actually had a minor arc on the latter first, thanks to its extensive international cast. Manson played Merida, the independent Disney princess from Brave, in eight episodes of the show's fifth season, where she ran afoul of King Arthur and the Dark Swan. Though she had a relatively short run on the show, her character made an impression on fans, who appreciated seeing the modern princess in live action.
Two years later, Manson played the Dryad in Legacies season 1, episode 5, "Malivore." The unnamed character was the first monster to provide Alaric with information about Malivore, which made her role critical given how much Legacies relied on Malivore as its main villain. In addition to providing much-needed exposition, the Dryad had an extremely sympathetic arc, as her heart was broken by her true love forgetting she existed. The depth of both supernatural roles likely helped Manson's career, as she went on to claim a main role on The Nevers.
8 Cassidy Freeman - Sage / Jack
Cassidy Freeman may be best known for her role as Tess Macher (Lena Luthor) on Smallville, but she also had critical roles in The Vampire Diaries and Once Upon a Time, building on the lore and backstory of both series. In 2012, Freeman ed the cast of The Vampire Diaries as Sage, the lover of Original Vampire Finn. Though she was only in three episodes, Sage was the one who taught Damon how to be a vampire, the one who burned down Whickery Bridge, and the first vampire to fall victim to the death of her Original sire.
Freeman's character on Once Upon a Time, Jack, was similarly important despite only featuring in one episode. Jack was Prince James's lover, who helped him trick the giant Anton and destroy the giants' homeland. While she was not one of Once Upon a Time’s best villains, her actions led to later conflicts between the last of the giants and Charming, who was identical to James, as well as adding a reason for why magic beans were so rare. Between the two roles, Cassidy Freeman remained a known face in fantasy television.
7 Alexandra Metz - Katie / Rapunzel
Alexandra Metz had minor roles on The Originals and Once Upon aTime, but both characters had serious impacts on their shows. In The Originals, Metz played a witch named Katie, who was in love with Marcel's right-hand man, Thierry. She revealed Hayley's existence to Marcel, which escalated tensions in the supernatural community, and nearly killed Marcel before she was stopped. New Orleans was a powder keg, and Katie's desire to maintain her relationship with Thierry nearly blew it apart.
On Once Upon a Time, Metz played the first version of Rapunzel — not Rapunzel Tremaine from the seventh season. Appearing in season 3, episode 14, "The Tower," Rapunzel was a princess who trapped herself in the tower due to her own guilt and fear. Meeting her helped Charming cope with his anxieties about being a father, but they also gave audiences a great discussion of how fear can lead to self-sabotage. Despite being a small part, this was vital to Charming’s character moving forward, making it just as important as her role as Katie.
6 Paul Telfer - Alexander / Lord Macintosh
Paul Telfer's big break came in 2015 when he was cast as Xander in Days of Our Lives, but when he was still trying to gain attention, he had brief guest arcs on The Vampire Diaries as Alexander and Once Upon a Time as Lord Macintosh. On The Vampire Diaries, Tefler played a member of the Brotherhood of Five named Alexander, who seduced and betrayed Rebekah Mikaelson. Alexander and his associates managed to dagger all five Originals, demonstrating how big of a threat the order of vampire hunters truly was.
On Once Upon a Time, Telfer played one of the lords who attempted to marry Merida. When she refused, he ed with other lords to oust her from power and kidnap her brothers. Though Lord Macintosh was briefly considered a villain, he eventually realized Merida's worthiness for the throne and fought to keep her in power. While still a minor role in the series, Macintosh was one of the few characters in the Brave arc who experienced real growth.
5 Jaime Murray - Antoinette Sienna / The Black Fairy
Jaime Murray has a pattern of playing characters with complicated morality, like her take on H. G. Wells in Elijah in the final season of The Originals. Out of love for her adoptive mother and brother, Antoinette convinced Elijah to stand against Klaus, which resulted in Hayley's death. Despite her role in that tragedy, she helped the family eliminate the other vampire purists, earning her freedom.
While Antoinette seemed to be a good person caught up with the wrong people, Murray's character in Once Upon a Time was far darker. Fiona, otherwise known as the Black Fairy, was responsible for making both Rumplestiltskin and Peter Pan into the villains they became, as well as being the primary antagonist of season 6. After kidnapping her grandson and turning him into her minion, Fiona attempted to defeat the Savior for good, willing to do anything to get the power she wanted.
4 Sebastian Roché - Mikael / King Stefan
Sebastian Roché is a common player in the supernatural fantasy genre, but one of his most prominent roles was on The Vampire Diaries and The Originals as Mikael, the powerful head of the Mikaelson family. Mikael was the primary reason Klaus became the villain he was known as, both due to his abusive treatment when Klaus was a child and his desire to kill his children for the next several centuries. While Mikael had a soft spot for his daughter Freya, he was otherwise a fearsome foe that Roché played with frightening sincerity.
When Roché appeared on Once Upon a Time, he took on a similarly cruel character in King Stefan. While he would otherwise be a sympathetic figure, having saved one princess from a sleeping curse and attempting to protect his daughter from the same fate, his taunts and condescension made the character easy to hate. Although not nearly as violent as the king in the villain origin story Maleficent, Roché's Stefan clearly enjoyed tormenting Maleficent. All of this came down to Roché's performance, with his skill at playing villains on display.
3 David Anders - John Gilbert / Victor Frankenstein
One of the most recognizable shared faces from The Vampire Diaries and Once Upon a Time is David Anders, who was in 14 episodes of the fomer and 15 of the latter. In The Vampire Diaries, Anders played John Gilbert, Elena's biological father and sometime antagonist of the first two seasons of the show. John had a complicated history with Katherine and vampires as a whole, but he ended up being defined by his love for his daughter.
Similarly complicated was Anders's character in Once Upon a Time: Victor Frankenstein. Victor's desire to create life led to his brother's death and his desperation to succeed in his experiments. Unlike other iZombie.
2 Nathan Parsons - Jackson Kenner / Nick Branson
Nathan Parsons has spent most of his acting career as Ethan on General Hospital, but he also made a point to various fantasy shows, including playing Jackson Kenner in The Originals and Nick Branson in Once Upon a Time. Jackson was one of the kindest characters in The Originals, standing by his intended fiance Hayley Marshall even when it meant fighting his fellow werewolves. Though their romance was in many ways a matter of necessity, Jackson did love Hayley and her daughter and put up with a lot of Mikaelson drama to be with her.
Parsons took on an entirely different role on Once Upon a Time, as his character Nick Branson was as far from a romantic hero as possible. In his original life, Nick had been known as Hansel, who fell prey both to a cannibalistic witch and the Wicked Witch of the West. To escape his past, he took on the name Jack, befriending Henry and living a heroic life until the show's fifth curse was cast, at which point he became a serial killer. The reveal was incredibly jarring, especially for those who were used to seeing Parsons as the strong yet kindhearted werewolf from The Originals.
1 Sara Canning - Aunt Jenna / Gretel
Sara Canning was the most prominent member of the Vampire Diaries franchise to Once Upon a Time, originally playing Jeremy and Elena's Aunt Jenna. She was a main character in the first two seasons of The Vampire Diaries, and while she didn't always know how to be the adult in the room, she did her best to take care of her niece and nephew. Jenna was the only main character with no connection to the supernatural world for the majority of her time on the show, and the way she got dragged into that world as a way to torment Elena was heartbreaking for fans to watch.
Canning's role in Once Upon a Time was much smaller than her 46 episodes of The Vampire Diaries, but it ended in a surprisingly similar way. Canning played Gretel, the sister to Nathan Parson's Hansel. While she initially seemed as sympathetic as Jenna, her character was willing to kill to get what she wanted. After being attacked by witches in her childhood, Gretel learned magic to keep from feeling weak ever again.