Gossip Girl may seem like an old, nostalgic series these days. However, its timeless story of drama and power struggle among the rich and privileged in New York’s Upper East Side is still just as entertaining today as the day its pilot aired. Along with showcasing ground-breaking fashion and brand new music, the series also did a commentary on family and mental health.
However, what truly made Gossip Girl special were the characters, inspired by the book series of the same name. Blair Waldorf successfully became one of the major Queen Bee characters in our history. In honor of her and all the other main characters, here are all of the series’ major stars and their D&D alignments, according to us.
Ivy Dickens: Neutral Evil
Ivy’s character is a highly debated one. As she’s hired to pose as Carol’s daughter in order to snatch part of CeCe’s trust fund, it’s obvious she’s at least partly in it for the money and for herself. However, over time, she grows attached to the people on the Upper East Side and falls victim to their scheming instead.
Ivy is among those characters who succumb to the vices of the Upper East Side. While she might come across small and weak at first, she develops a strong character and isn’t afraid to try and have her way; for example, when Charlotte Rhodes gives part of the inheritance to Ivy and tells her to destroy the Van der Woodsens. This makes her a solid, selfish Neutral Evil.
Vanessa Abrams: Chaotic Good
Down to earth and incredibly kind-hearted, Vanessa usually appears as the odd one out among the scheming rich and famous on the Upper East Side. She’s a serious student who dreams of making a film one day, and she frowns upon those who are obviously more fortunate and wealthier than her.
Vanessa’s dislike of Blair and her scheming shows that she values manners and kindness above all else. When she does eventually succumb to scheming herself, Vanessa is usually shown to be upset with herself, due to becoming the very thing she absolutely despises. Still, we give her a solid Chaotic Good alignment based on her desire to do good.
Rufus Humphrey: Lawful Good
There are few extremely good characters in the series, but Rufus is definitely one of them. Much like Vanessa, he has a big and kind heart. With a strong sense of right and wrong, he’s often the first to point out when people have done wrong but will also try to see the good in them.
Despite Rufus’ relationships with Lily, he’s a character that rarely gets hooked into the drama of the series. With an extraordinarily clean record, Rufus makes the cut for a Lawful Good character, who respects the rules in place and seeks to do good within a given set of rules.
Lily van der Woodsen: Lawful Neutral
Lily has always lived a very privileged life, despite her teenage rebellion years. She’s the daughter of a music producer and heiress of the Rhodes empire. Her marriage with William only solidifies her position as a major socialite on the Upper East Side, with tons of connections.
Although she once rebelled against her family, Lily’s shown to care a lot about her family’s image and the behavior of her children. She became the very thing that she once fought against, and is trying hard to instill that into her children. Lily is a Lawful Neutral, who is simply following in CeCe’s footsteps to keep the family empire going.
Chuck Bass: Neutral Evil
Chuck is a character that underwent a tremendous amount of growth during the series. Initially, he comes across as selfish and violent as he tries to assault Jenny Humphrey, Chuck eventually grows up to be a cutthroat businessman with only a few well-chosen friends. Clever and hot-tempered, he’s the bad boy of the series.
It would be hard to classify Chuck as a Good or Neutral character due to his scheming ways. After a challenging relationship with his father who never sees Chuck as good enough, it’s safe to say he’s a Neutral Evil with a few select accomplices.
Jenny Humphrey: Chaotic Neutral
Another character that grows exponentially during the series is Jenny. She begins as a mere newcomer and ladder climber among Blair’s servants, only to put her foot down and become her own personality by changing her style and rebelling against those around her.
Jenny doesn’t seek to do good or bad, nor is she particularly selfish. Her intentions change as she matures into her own ambitious self with original thoughts and ideas. After working under Blair, Jenny learns to not let others walk all over her, which puts her at the hard-to-define Chaotic Neutral alignment.
Nate Archibald: Chaotic Good
Sweet and handsome, Nate is your classic jock character, with his heart in the right place. Despite being at the center of all the drama, he often finds it hard to relate or enjoy it for that matter. He comes from a lot of wealth, but he’s truly down to earth, if not a bit gullible at times.
Nate is driven by a deep desire to please everyone around him and is unable to tell convincing lies. Although he’s often seen with questionable partners or older women, Nate just wants to do the right thing and find someone he can have a real connection with. A Chaotic Good, Nate’s gullible and naive nature truly putting the Chaotic into his personality.
Dan Humphrey: Neutral Evil
Dan doesn’t come across as anything special or evil. In fact, his character is one of the kindest in the show, even if he does get hooked into a lot of scheming through his relationships with Serena and Blair. He’s desperate to fit in and be a part of the Upper East Side, while also despising the experience.
However, since “Gossip Girl” is the primary evil depicted in the series, and it’s revealed that Dan is the person behind the blog, it’s pretty evident he has a deep, selfish part within him. While Nate does grow throughout the show, it would be impossible to say he didn’t seek to ruin countless lives with his blogging, making him a Neutral Evil.
Blair Waldorf: Lawful Evil
Highly ambitious and fiercer than any other character on the Upper East Side, Blair is undoubtedly the Queen Bee that everyone calls her. She’s extremely competitive and a mastermind behind all the drama and scheming that goes on in the series, which ends up with her often hurting and humiliating people who oppose her.
Blair does fit the classification of an Evil character, but she’s an authority figure with a following, which makes her Lawful. She uses her power and her followers to get what she wants and feels like she deserves.
Serena van der Woodsen: Neutral Good
Although Serena is considered the “It” girl of Upper East Side, she’s by no means an elitist. Warm and friendly towards just about anyone, and rarely seen as acting selfish, Serena isn’t typically judgmental and harsh towards those she first meets, despite her troubled past.
That being said, even Serena can sometimes scheme and break the rules in place, which makes her a Neutral character depending on her approach. Deep down, however, she’s a good person who doesn’t enjoy hurting others.
