17. Dorota
16. Cyrus
15. Eric
14. Nate
13. Rufus

Bart Bass was evil incarnate, but Blair Waldorf really wasn't that bad!
I'm not being dramatic when I say I would die for Dorota. She was such an amazing parental figure to Blair. She was loyal to a fault and truly loved Blair. I adored her relationship with Vanya and honestly smiled every time she was on screen. She had absolutely zero faults and I will fight anyone who says otherwise.
Another truly beautiful soul. Now that I think about it, Blair had a lot of really positive parental figures. Not only was Cyrus smart (he outmaneuvered Blair when she tried to undermine him, causing Blair to respect him), but he was endlessly loving. He was an amazing husband to Eleanor and a great father to Blair. When Blair asked him to walk her down the aisle with her other dad, I cried. CYRUS 5EVER.
Oh, my poor bb Eric. You deserved SO MUCH BETTER than a family with Dan, Serena, Lily, and Chuck. He was the voice of reason, and the only one who actually told it like it was. He also was SO loyal and always there for his friends when it mattered, even when they didn't deserve it (cough cough, Jenny cough cough).
Nate did a few bad things, but I'm not entirely convinced he knew any better (except for sleeping with Serena – seriously???) He always had good intentions, but he was a little bit of a dum-dum. He also literally NEVER SENT IN A TIP TO GOSSIP GIRL, which makes him better than the vast majority of the characters. Oh, my sweet summer child. You should have found new friends.
Rufus really tried. He was overall a good father to Jenny and Dan, and even Lily's kids. I have to take points off for Jenny and Dan turning out so horrible, though. Also for sleeping with Ivy – that was a questionable decision at best. Still, definitely the best of the blood-related parents.
Eleanor started out kind of bad (remember the photoshoot episode?), and I definitely think she could've been there for Blair a lot more. However, she really came into her own when she married Cyrus, and in the latter half of the series she was a great role model for Blair. She supported her and also cut through all Blair's bullshit to understand what she really wanted and needed.
Was Blair scheming, lying, and manipulative? Yes. But she also had a really great heart, and she cared SO MUCH about everything and everyone. Serena was a horrible friend, and Chuck was a horrible boyfriend, and she was always there for them when they really needed her. She fought for the people she loved, even if her personality was bitchy. In the grand scheme of this show, Blair was DEFINITELY not among the worst.
Vanessa sucked and I hated her, but that doesn't make her a bad person. Still, some of her actions were questionable, like helping Juliet scheme to ruin Serena's life and having Dan's book published without his permission. She was also just so negative and thought she was better than everyone because she wasn't rich, just like Dan. Mostly, I'm putting her below Blair because even though she was much less scheming, I can't remember many times she was actually a good friend.
Ivy full on conned the Van Der Woodsens, but...they kind of deserved it, and hey, a girl's gotta make money. However, she also sent the tip to Gossip Girl that resulted in Chuck and Blair's car crash. She dated Rufus while working with William in some scheme to undermine Lily, and overall just never really owned up to her actions. She was kind of trash, but I do think she had a semi decent heart.
Jenny was corrupted young, so I can't hate on her entirely. But she was obsessed with social climbing and put Rufus through SO MUCH that he didn't deserve, considering he was a pretty decent father. She constantly schemed against her own family, including Serena (working with Juliet, trying to sabotage Serena's relationship with Nate) and her own father (working with Will to sabotage her father's relationship with Lily). She was also a horrible friend to Eric. Honestly I just can't think of very much good she did for anyone.
Lily had her moments (she was a good parental figure to Chuck), but she also did SO MUCH messed up stuff. Like signing Serena's name on an affidavit to falsely accuse a teacher of statutory rape and put him in jail for years. Or having Rufus's son and not telling Rufus about it. She cycled through husbands like new purses, subjecting her kids to a ton of uncaring father figures, culminating in her son's suicide attempt. She cared way too much about status and projected those ideas onto her children.
Georgina had her issues for sure. Especially in Season 1 – she literally blackmailed Serena with a snuff film and weaseled her way into Dan's life by pretending to be someone else. But after that...she was actually more funny than bad. Except for pretending Milo was Dan's son. Yeah, that was...not great.
I have a soft spot for Chuck even though he absolutely doesn't deserve it. He had a horrible upbringing and horrible role models, so a lot of his actions make sense. But...he tried to sexually assault both Jenny and Serena in the pilot, and that is inexcusable. He also (accidentally, yes) hurt Blair and that was messed up. And selling Blair for the hotel...too far. Sorry, Chuck, you're in the top five worst characters.
Oh, Serena. Serena, Serena, Serena. Let's quickly run through the worst things she did: she had sex with Nate when he was dating her best friend, she had revenge sex with Dan and RECORDED IT to hurt Blair, she gave cocaine to a drug addict causing his overdose, she messed with Rufus and Lily's relationship by siding with her father WHO CONVINCED LILY SHE HAD CANCER, she hurt Blair's chances of going to her dream school, and she constantly undermined people whenever they got more status than her (Blair, Lola). Serena was a terrible person and friend 90% of the time, and the worst part was she always pretended like she was better or was trying to put the past behind her, but she never actually did. Honestly, her and Dan kind of deserved each other.
Jack was THE WORST. He literally tried to BUY Blair off Chuck, just to ruin Blair and Chuck's relationship. He constantly schemed to get Bart's company and sabotage Chuck. He was so selfish and just a horrible role model, not to mention smarmy and gross. In the end, he did help Chuck and Blair after they sort of killed Bart, but it didn't make up for everything before!
Dan was Joe Goldberg Lite and that's just the gospel truth. I don't care how Serena excused away his actions (are we really going to trust her judgement??), he ruined all their lives. He was the reason the paparazzi chased Blair, causing her to get in a crash and lose her baby. He literally started the site with a post about a 15-year-old Serena wearing a white dress that got water on it, allowing people to see under her clothes. And then HE WROTE HIMSELF into the blog in order to have a chance with her. Then he wrote a book profiting off all of them. He was just a trash person. Even before we found out he was Gossip Girl, he was just so entitled and never acknowledged that he was privileged too.
Look, I would've loved to put Dan first, but Bart was truly evil incarnate. He was a horrible father who blamed Chuck for his mother's death (but then his mother was actually alive?? I'm still so confused). He constantly made Chuck feel worthless. And then he FAKED HIS OWN DEATH, leaving Chuck to his own devices for years until he came back, tricked Chuck and stole his company back, called him weak for loving Blair, and then TRIED TO KILL HIM. Satan who?? I only recognize Bart Bass.