Gossip Girl
Summary
While Blair Waldorf , Chuck Bass , and their crew of loaded friends are n’t exactly the most likable people , some of the worstGossip Girlcharacters are the supporting ones . base on the Cecily von Ziegesar book serial of the same name , Gossip Girlcenters around a chemical group of inside teens in New York City ’s Upper East Side whose personal lifespan are reported on and skewer by the eponymous , anon. blogger . The show ran for six time of year from 2007 to 2012 and inspired ashort - livedGossip Girlreboot seriesthat debut on Max ( then known as HBO Max ) in 2021 .
Gossip Girlmade Brobdingnagian star out of its independent cast , particularly Blake Lively ( who played Serena van der Woodsen ) and Penn Badgley ( Dan Humphrey ) . But the teen drama also provided many opportunities for guest role player to make their print , whether they play school rivals or making love interests of the lead characters . Some actors even had guest roles onGossip Girlbefore they were famous , like Sebastian Stan ( Carter Baizen ) and Rachel Brosnahan ( a nameless " Girl " ) . Unfortunately , not every patronize player was embraced by the fanbase , and many inadvertently vied for the title of most detest character inGossip Girl .
12Jenny Humphrey
A lot of people did not like petty J , even though she came from the nicest and most normal family on the show . She really want to agree in at school and rise up from Brooklyn to the fairy of Constance . To accomplish this , she lost herself a bit and did not seem to care that she was ache her loved ones and hurting herself . She steal , lied , cut class , picked up mean little girl behaviour and totally close out the citizenry who already like the original and old Jenny .
The trouble with Jenny ’s descent into assay villainy is that it was n’t gradual . It ’s like she was two different people — unfermented little J and condemnable backstabber . Jenny also attempted to take over Blair ’s military position of magnate , and the consultation loved Blair Waldorf as Queen B. When Taylor Momsen decided to leave the show , The most humbling way out inGossip Girlhistory , Jenny was literally banished from Manhattan by Blair — who was perhaps speaking for the consultation .
11Vanessa Abrams
Another character who was ostensibly presuppose to be likeable but was n’t at all was Vanessa Abrams . She was a childhood Quaker of Dan ’s , and she claimed to dislike the Upper East Side , though she never seemed to leave it . She even dated Nate Archibald , one of the richest mass in the neighborhood . Gossip Girlhad a great opportunity to comment on wealth and privilege through Vanessa and have her be the voice of the audience , but she just add up across as a phoney .
Vanessa also date Dan , and though hearing ordinarily root for the childhood crush to win the object of their philia , Vanessa just did n’t have the same chemistry with Dan that he had with Serena . And compared to Serena , and specially Blair , Vanessa ’s storylines just did n’t have the same bite and often dragged the show down . Like Jenny , Vanessa also end up act away , as actress Jessica Szohr left the show , and though Szhor is a gifted actress , herGossip Girlcharacter was n’t drop .
10Lily Van Der Woodsen
Lily van der Woodsen is inGossip Girlfrom the beginning to the terminal , but she ’s commonly a background instrumentalist in her girl Serena ’s life history . While Lily spends a lot of time saying she wants her children to have more grounded lives , and she seems to be a well - meaning mother , she does n’t pass a lot of sentence commit the same advice she dish up out , which makes sort of makes her and Vanessa opposite sides of the same coin — they both amount across as wildly hypocritical .
This is specially true when it comes to Lily ’s relationship with Rufus . She makes a muckle of the same error with him that her girl build with Dan , despite having already learned from them when she was in eminent school . Gossip Girlseason 2 , episode 24 " Valley Girls " featured actress Brittany Snow as a immature Lily in flashbacks that were meant to function as a backdoor sequence for a spinoff series . The spinoff never came to fruition , and though more Brittany Snow is always a good matter , Gossip Girlfans were n’t sad to miss out on a show all about Lily .
9Jack Bass
Blair Waldorf is hardly the kindest person in the human race , but she is by and large considered to bethe bestGossip Girlcharacter . Therefore , wronging Blair is the biggest primal sinning anotherGossip Girlcharacter can confide . And Jack ’s hell is uncollectible than most , as he is beyond sleazy in his intervention of Queen B. From the moment he meet her , Jack sees Blair as a seduction and a sex object , and in one ofGossip Girl ’s most disconcerting storylines , he tries to " purchase " Blair from Chuck in central for a hotel . It ’s also worth noting that Chuck is no practiced than Jack , as he check to the peck .
In later seasons , Gossip Girlattempts to give Jack somewhat of a repurchase arc , as he advance Chuck to fight for Blair , and he ’s also the one to slant off thefan - favoriteGossip Girlcouplethat the police are after them and propose they get conjoin for spousal prerogative — advice that they take . But in terms of Jack ’s likability , one favour , no matter how crowing , does n’t forgive what is essentially attempted human trafficking .
8Georgina Sparks
Georgina Sparks was aGossip Girlside lineament with main character energy — at least , fit in to her . Since her reaching in season 1 , Georgina was on a one - woman warpath to mess up up the lives of the Upper East Side teens , specially Serena ’s . But unlike Jenny and Vanessa , whomGossip Girlfans truly wanted off the show , Georgina ’s chaotic vigor was always a welcome plot line and she was a character that audiences loved to hate .
In some ways , Georgina was a combining of Serena and Blair ’s bad traits . She was a party girl like Serena , though she direct her savage - tyke antics to a whole Modern grade , and Georgina was also a plotter like Blair . However , Blair ’s scheming , no matter how cruel , was always in the name of keep herself on top ; Georgina was just hook to end . Georgina was in a kinship with Jack Bass at the ending ofGossip Girl , and there were n’t two characters who deserved each other more .
7Bart Bass
Bartholomew " Bart " Bass managed to pull off the unacceptable inGossip Girl : make Chuck sympathetic . Though Bart ’s opinion that his son was nothing more than an irresponsible playboy was largely genuine , there is nothing that Chuck could ever do that would please or impress his Fatherhood . Bart treat Chuck and the other members of his family like chess piece , even keeping secret file on them .
ThoughGossip Girlfans were no rooter of Lily , specially how she behaved in her relationship with Rufus , nobody could deny that the two had chemistry and were entail to be together . Bart throw a wrench in this and end up get hitched with Lily , which broke Rufus ' heart and bring up buff ' rage . As pachydermatous as it may be , nobody was happy to seeBart come " back from the dead " , nor was anyone sad when he leftGossip Girlfor secure .
6Sage Spence
Over the years , Serena go out several Guy , and one of them was Steven Spence , who had a daughter named Sage . Given the geezerhood gap between Steven and Serena , she was only four geezerhood older than Sage , which can finger awkward and be gruelling for a child to accept , even a teenager .
But it ’s surd to find benevolent for Sage when she pulls Georgina - floor stunts to conk out up Steven and Serena , which has a ripple effect for Serena and even her friends , like when Sage ruined Blair ’s fashion show . But ultimately , Sage was not around for long , as Serena and Steven ’s uncomfortable kinship was mercifully short - lived .
5Agnes Andrews
While theGossip Girlfandom was no fan of Jenny Humphrey , it was absolved that she was a gifted fashion designer , and within her work , she meet a role model named Agnes Andrews . The two decided to go into business together , which was a mistake on many levels . Agnes was inept and lazy , and for once Jenny was really in the right when she split ways with her . Agnes ' response — taking all of Jenny ’s designs , throwing them into a dumpster , and setting them on fervidness — said it all .
Jenny was the worst principal character , but at least she was still intrench in the main drama of the show . Seeing anyone other than Blair take Jenny down a peg just was n’t as playfulness . at last , Agnes was more mean - enlivened than ambitious .
4Diana Payne
While Elizabeth Hurley was amongGossip Girl ’s starry Edgar Albert Guest actors , her role was n’t incisively beloved . Diana Payne was fairly one - note as an intrepid femme fatale keen on seduce Nate and using him and his family to further her career atThe New York Spectator .
Nate is hardly the most interestingGossip Girlcharacter , but that ’s because the all - American teen never tried to backstab anyone . Seeing someone like Diana go after such an innocent person just is n’t fun to check , and it would have been a better storyline if some of her feelings for Nate were real .
3Juliet Sharp
Another scheming woman who dated Nate was none other than Juliet Sharp . It turned out that this reference ’s brother , Ben , was put in prison because of Lily van der Woodsen .
While struggle for a menage member ’s justice is understandable , Juliet took it right smart too far . She falsely tipped off Gossip Girl that Serena had an STD and even drugged her . Juliet was so individual - minded in her nidus on Serena that there was n’t room for any other narrative with her . She was less of a character and more of an obstruction in Serena ’s life sentence , albeit a evil one .
