Top 10 Times Chuck Bass was the Worst on Gossip Girl

Top 10 Times Chuck was the WORST on Gossip Girl

Welcome to MsMojo, and today we’re counting down our picks for the Top 10 Times Chuck Was The Worst On Gossip Girl.

For this list, we’ll be looking at the most inappropriate, terrible, or questionable things Chuck Bass did on the hit CW drama. We’re also issuing a spoiler warning.

What are your thoughts on Chuck? Let us know in the comments!

#10: The Way He Treats Lily After Bart Dies
“O Brother, Where Bart Thou?”

After Bart dies, Chuck is in a really dark place. He takes it out on everyone around him, namely Lily. He blames her for his dad’s death and makes sure to tell her so. She was going to leave him for Rufus and Bart was on his way to talk to her when he died. What he basically calls her at the funeral and the wake is pretty tasteless. To be fair, Chuck’s relationship with Bart and the concept of family was always a complicated one and he’s grieving. But Lily tries so hard to be kind and motherly and he pushes her away so viciously. Thankfully, these two eventually patch things up and truly become family.

#9: “That’s Too Bad” Response
“O Brother, Where Bart Thou?”

Blair does everything she can to be there for Chuck after his father’s death. He is being distant and cold, yet she refuses to give up on him. She actually ends their game and tells him she loves him. It should be a moment of light amidst the darkness, but he's in such a bad place he responds, “that’s too bad.” Sure, he’s struggling with Bart’s passing, but that doesn't make this remark any less cruel - especially considering how Blair puts her ego aside to tell him how she feels. Instead of letting her in, he completely shuts her out. Later on, he goes to her in bad shape and she comforts him despite his nasty behavior. If that’s not love, we don’t know what is.

#8: When He Goes After Blair Behind Nate’s Back
Various

Chuck and Blair are an iconic couple, but their start has a questionable aspect we sometimes overlook. When Blair and Nate break up, she goes to see Chuck at the burlesque club and does a dance onstage that mesmerizes him. They sleep together, and Chair is born. Except he’s supposed to be Nate’s best friend, so it's actually a pretty shady move. He also continues pursuing her behind his back afterward. It seems to be the first time Chuck has real feelings for a girl, and it’s hard not to root for them, but it’s also impossible to ignore the lies, and disregard for a supposedly sacred friendship. No matter how you slice it, that’s just not okay.

#7: When He Shames Blair on Gossip Girl
“A Thin Line Between Chuck and Nate”

Blair might be pregnant and she’s not sure if Chuck or Nate is the potential father. It’s revealed to be a false alarm, and she tells Chuck to move on from her. Angry that she’s choosing Nate over him, he sends a tip to Gossip Girl exposing how the pregnancy test was hers, and that she slept with two guys in one week. This is how Nate finds out about Chuck and Blair, and she becomes a social pariah. When she goes to him defeated, he actually compares her to one of his father's Arabian horses. He basically tells her he’s not interested since she’s not “pure” anymore, whatever that means. It’s crude and callous behavior on his part all around.

#6: When He Abandons Blair All Summer
“Much ‘I Do’ About Nothing”

Chuck Bass can break hearts as quickly as he can melt them. He woos Blair, and they decide to pursue a relationship and go to Europe together. That is, until Bart gets in his head. He tells him that having a real girlfriend will make him an adult. His father views this as a positive thing, but it’s Chuck’s worst nightmare. Faced with the prospect that his days of debauchery could be over, he chickens out. Instead of meeting Blair, he just leaves her stranded on the helipad alone and goes off with another woman. He tells Blair he’s running late and will meet her in Europe. Of course, he’s lying and never does. It’s a return to his old ways, and it’s a shame.

#5: When He Hooked Up with Jenny
“Last Tango, Then Paris”

Blair has to make a choice: meet Chuck at the Empire State Building or lose him. She decides to go, but Dorota goes into labor so she’s late. Chuck is gone when she arrives. Apparently, the kids in this city can text Gossip Girl, but not each other. Thinking she’s rejected him, Chuck sleeps with Jenny. It’s a colossal betrayal to Blair: Little J is her nemesis, and he should have waited more than 15 minutes for her. Plus, Jenny is 16 and vulnerable, while he’s an adult. When Blair shows up, he acts like nothing’s wrong. The truth does eventually come out as he’s about to propose, and a devastated Blair leaves him. It’s an affair to remember, and not in a good way.

#4: When He Exchanges Blair for His Hotel
“Inglourious Bassterds”

Jack Bass has Chuck’s hotel, and the young Bass wants it back. When it turns out Jack’s price is Blair, Chuck agrees. Instead of scheming with Blair to defeat Jack, he lies to her. He pretends he doesn't know that Jack is propositioning her - and later claims it would’ve been obvious they were working together if he had told her his plan in advance. Thinking he has no clue, she agrees to have sex with Jack. He kisses her and then stops because what he really wanted was to ruin their relationship. When she realizes Chuck played her, she’s understandably heartbroken. Not only did he lie to her, but he also treated her like property. It’s no wonder she walks away, we would have too.

#3: What He Tried to Do to Serena
“Pilot”

Chuck sees Serena at the bar and tries to flirt with her. She’s not interested and replies that she’d rather eat something. He offers her a fancy sandwich from the kitchen, and when she accepts he tries to sleep with her. As if a sandwich entitles him to sex. He tells her he saw her and Nate hook up at the Shepherd Wedding. As if that somehow means she should now sleep with him too. He keeps coming on to her. She refuses his advances, but he doesn’t listen and tries to force himself on her. Luckily, she manages to push him off and rush out of the hotel. If they were trying to make Chuck the villain of the first season, they certainly succeeded.

#2: What He Tried to Do to Jenny
“Pilot”

At the “Kiss On The Lips” party, Chuck lures Jenny into a quiet spot to “talk.” He kisses her but she makes it clear she doesn’t want to do anything. He pretends to understand but she realizes he’s dangerous and texts Dan for help. When Serena and Dan arrive, they find Chuck on the roof with Jenny and thankfully manage to stop him from doing something unspeakable... It’s extremely predatory behavior and unfortunately standard for Chuck. After all, when Serena finds out Jenny is with him, she instantly knows what’s happening. Even he later realizes how reprehensible it is, eventually apologizing to Jenny over a year later. Too little too late or better late than never? You decide.

#1: When He Shoves Blair & Punches the Window
“The Princesses and the Frog”

Chuck and Blair have a complicated story, and it takes a lot before he becomes her prince. There’s a party and Blair, who is with Prince Louis, needs to gain his mother’s approval. Chuck crashes to try and win her back, but makes a scene and embarrasses her in front of the Royals instead. Louis proposes anyway and she accepts. When she goes to tell Chuck, he becomes possessive and violent. He pushes her and punches the glass wall behind her, cutting her face. At this point, one could only wonder: will he ever learn that Blair isn’t his property to keep or give away? The possessive ex-boyfriend with a temper isn’t a good look on anyone, not even Chuck Bass.