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The Romanticizing of Chuck Bass - by Chrisinda Lynch

[This profile contains discussion of abuse and sexual assault.]

Season 3

By the premiere, Chuck has taken over Bass Industries. Inspired by the movie Wall Street, Daman decided to outfit season three Chuck in Gordon Gecko–like banker’s collars, paisley ties, suspenders, cuff links, and monogrammed pinkie rings (“Gossip Girl Style with Eric Daman”). Let’s take his opening look as an example: a blue-striped banker’s collar shirt, red suspenders, and blue paisley tie. Despite Chuck’s desire to distance himself from Bart, to make his own name, he can’t help but emulate his father in his dress, picking up banker’s collars and other fashions of the decade Bart came to prominence.

Chuck and Blair have been dating for a few months, their color palettes still perfectly coordinated. In episode three, Chuck decides to sell all his Bass shares to buy the Empire Hotel, risking his father’s legacy to forge his own. Fittingly, he looks much more like season one or two Chuck: a dark gray suit with pale pink striped shirt, peach bowtie, and floral pocket square. Blair picks up his pastels and florals in her own ruffled lilac tank and black floral skirt. “How can you be so sure [about buying the Empire]?” she asks Chuck.

“Because you believe in me,” he replies: a sweet moment, made bittersweet by the story lines to come, the enormous toll Chuck’s Empire will take on their relationship.

For games will always be a part of Chuck and Blair’s relationship; at the beginning of the season, they played “Scorned Girlfriend,” Blair pretending to discover Chuck just before he kisses another woman. In episode six, Blair re-ups the game to secure the freshman toast at her new college, NYU—but this time, she doesn’t interrupt before Chuck is kissed by her target, the man tasked with choosing the toast giver. “You really think I’ve never kissed a guy before?” Chuck says after, and while I’d like to think the show was creating a canon bisexual character, I think Chuck’s kisses, like his fetishization of women of color, are meant more as a mark of sexual “deviance” than any real representation.

After a must-attend opening of the Empire’s club, Chuck and his hotel are on their way to success. Nevertheless, the ghost of his father still haunts him, most literally in episode twelve. On the anniversary of Bart’s death, Chuck chooses a stark white shirt, black suit, black-and-gray tie, and dark red pocket square—like his funeral outfits, though much tidier.

In a very Christmas Carol story line, Chuck is considering turning a homeless shelter into lofts. He is visited by visions of his father, who loves the idea. Vision Bart dresses much as he did in life: black suit, pale blue shirt, and red-and-blue tie, but with an undertaker-like black coat on top. “I haven’t seen anything in the last year that suggests you have what it takes,” he tells Chuck. “If anything, you’ve been a disappointment. You opened your heart to Blair and it made you weak.” It’s a fascinating vision, Bart’s words filtered through Chuck’s fears. After all, Bart was the one who encouraged Chuck to date Blair at the end of season one, who thought the relationship would make him more mature. In a way, he was right: That night, Serena gets into a car accident, and Chuck is finally able to leave his visions behind, to face the grief and self-doubt he’s been carrying for a year. “You’re becoming a man in a way that your father never was,” says Blair.

Chuck visits his father’s grave with a bouquet of yellow roses, his mother’s favorite flower. There, at Bart’s graveside, is a woman laying the same bouquet alongside a locket with Bart’s picture inside. Considering the Bass habit of gifting women necklaces, it should come as no surprise that this woman is Chuck’s long-lost mother, Evelyn Bass.

Chuck initially resists a relationship with his mother, but by episode fifteen, he’s ready to let her in. She gifts him a purple bowtie that Blair helped her pick out, telling him that purple was Bart’s favorite color, too. Chuck thought Bart “loathed” it, but Evelyn says Bart was “always playing with people’s heads.” His mother even wears purple earrings in the scene, Chuck in a Bart-like dark suit, blue banker’s collar shirt, and red tie.

He’s worried about a new lawsuit: “several female employees at the Empire are suing [him] for sexual harassment.” Chuck claims the accusations are fake, though he admits that there were incidents at the Palace hotel when he was “a kid.”

To save the Empire from bad press, Chuck signs the hotel over to his mother—realizing, too late, that she is in cahoots with his uncle Jack and his lawyer. Jack takes over the Empire and kicks Chuck out of his suite, even puts on Chuck’s purple paisley smoking jacket (3.17). He’s assuming Chuck’s body, even sexually: Jack offers to trade the hotel for one night with Blair. Blair agrees, believing she’s going behind Chuck’s back, only to discover that Chuck set her up. Chuck tries to pin equal blame on Blair, even though he created an impossible choice: Blair can stand by while Chuck loses everything or sleep with Jack and lose her own boundaries.

“I did what I had to win,” Chuck tells Blair. “I can’t let my feelings cost me all that I’ve built.” He’s still warring with that vision of his father, trying to prove his relationship hasn’t made him “weak.” He’s even wearing the gloomy colors of the funeral and anniversary episodes: gray striped button-down, gray paisley tie, and black coat. 

Chuck has the hotel, but he’s lost Blair, at least for a few episodes. They’re still drawn to each other, Blair understandably unsure about getting back together with him. Then, Chuck sets a ticking time bomb: Blair must meet him on the observation deck of the Empire State Building the following day or he’ll be lost to her forever. Though Chuck intends to reference An Affair to Remember, I think he’s more likely to remind her of the other Empire he traded her for.

Blair goes to the deck, only to find a bouquet of pink peonies in the trash; as Chuck later reveals, he left after only two minutes and went back to his suite at the Empire. Jenny arrives, looking for Nate, and they drink together; that’s what she must do, he says, to hang out with him. Chuck is still wearing the blue pinstriped suit and pale blue striped shirt he wore to the deck, but his pink bowtie is gone, his collar undone. Soon they kiss and then sleep together, Chuck yet again crossing lines of consent. Perhaps he learned enough to stop Lily’s assault, but he hasn’t yet learned that he shouldn’t sleep with a distraught girl who doesn’t “want to be alone,” that he shouldn’t expect his girlfriend to sleep with another man to save him.

After Blair arrives at Chuck’s suite and they reunite, Jenny must sneak out like a shameful secret. Chuck was planning to propose, and he almost does before Dan punches him and forces him to tell Blair what he did to Jenny. Blair and Chuck break up, again, and Chuck escapes to Prague. In the red-light district, two men mug him, and he’s shot when he won’t let go of Blair’s engagement ring. 

Season Four

Chuck is rescued by a young Frenchwoman named Eva, who takes him to her apartment and tends to his bullet wound. As Chuck writhes in pain, his memories flash by: he assaults Jenny and Serena in season one, Nate confronts him about sleeping with Blair in season one, Blair slaps him after the hotel trade in season three, and finally, Dan punches him for sleeping with Jenny in season three. Then Eva’s face comes into focus; she looks like a saving angel, like he’s just exorcised his demons. He’s now dressed in a clean white T-shirt, his wound bandaged—perhaps the simplest, most common look we’ve ever seen Chuck in. Eva asks him his name, and he looks to the nightstand, where a copy of Henry V rests.

“Henry Prince,” he replies and slips off his pinkie ring from the previous season, monogrammed with his old initials.

“Henry” moves to Paris with Eva, takes his first working-class job as a waiter. He thinks this new life, away from the Upper East Side, is “a chance to live simply, earn people’s respect. Maybe become a person somebody could love.” Indeed, his wardrobe is simple: lots of jeans and chambray shirts, brown leather belts and shoes, white undershirts. Daman cites his inspiration for Henry as James Dean in East of Eden; I also see hints of Marlon Brando in A Streetcar Named Desire. It’s the kind of wardrobe a wealthy person might imagine a working-class person wearing, based only on movies they’ve seen—the collars, quite literally, blue. 

Serena and Blair track down Chuck in Paris, and Blair convinces him to come home (4.2). After revealing his real identity to Eva, he takes her with him. This is new Chuck, “good” Chuck, in love with the angelic Eva: pastels, little flower pins, floral print ties. Unfortunately for Chuck, moving on from his past isn’t as easy as changing his wardrobe, and fitting Eva into New York society isn’t as easy as buying her a designer dress.

In episode three, Eric tells Rufus that Chuck sleeping with Jenny was not an “isolated incident”—interestingly enough, while Rufus helps him knot a bowtie, a season one Chuck staple. Rufus later confronts Chuck at a Fashion’s Night Out party, Chuck clad in his new style: a windowpane navy suit, striped white shirt, floral blue tie, and white flower pin. “I apologized to Jenny; she forgave me,” he tells Rufus, and while the former is true, we saw nothing of the latter on-screen. Eva interrupts their conversation, and Chuck, not wanting her to learn of his past, pretends not to know her, cruelly calling her a “social climber making a play for Chuck Bass.”

Lily later takes Chuck aside and says that Jenny already told her about the assault. According to Lily, Jenny wants “to put the past in the past and . . . move on.” Again, the show is retroactively writing scenes to facilitate Chuck’s redemption, all his sins purged through a bullet hole.

In episode four, Chuck wears his largest flower pin yet, to the party where he announces a new charitable foundation in Eva’s name—appropriate, as this is the very peak of good Chuck. He pairs the white pin with a black suit, blue bowtie, and white shirt. At the party, a jealous Blair reveals that Eva was a sex worker in Prague; she even plants Chuck’s recovered wallet in Eva’s suitcase. Eva is using him for his money, Blair says, just like his mother.

Chuck breaks up with Eva, only to discover Blair’s deception; unsurprisingly, he blames Blair for his reaction: “Eva made me into someone I was proud to be,” he tells Blair. “You just brought back my worst self.” Chuck and Blair are at war for a couple episodes, then move on to hate sex. They almost begin dating again but decide to wait until Blair has figured out her career path.

Chuck shifts his attention to his company; turns out going missing for a whole summer can have a negative impact on your business. Bart’s old friend and rival Russell Thorpe is planning to buy Bass Industries, and Chuck tries to stop him—partly by getting cozy with his daughter, Raina, for a few episodes. She’s exactly who Chuck always wanted to be: her father’s closest advisor, respected and loved but given enough freedom to have fun.  

As Chuck develops real feelings for Raina, they start to share the same color palette, just as he once did with Blair—bold purples, reds, blues. Raina favors sleek, solid dresses, while Chuck chooses suits with printed shirts and ties—gone are the suspenders and banker’s collars of last season.

Indeed, the person most likely to wear a banker’s collar this season is Russell. In episode seventeen, he reveals that Raina’s mother, Avery, died in the same fire Dan almost wrote about in season two. In this scene, Russell wears a pale blue banker’s collar shirt, yellow tie, and dark suit, while Chuck pairs a white-and-blue-checked shirt and blue tie with his own suit. It’s almost like he’s facing his own father, staring head-on at a long-hidden truth. “When my father died, we were in a good place,” he tells Russell. “You’re trying to rob me of that.” And yet, Bart and Chuck weren’t in a good place—Bart had just blamed him for his troubles with Lily.

Chuck spirals from there, drinking, telling Serena: “All I ever wanted was to know [Bart], for him to let me in. He lied to me until the day he died.” After Blair begins dating a prince of Monaco and Raina starts searching for her mother, Chuck reverts even further back into his old ways. He’s like Chuck in the episodes following Bart’s death: dressed in dark colors, unshaven and untidy.

Even the fashion-unconscious Nate notices Chuck’s black silk robe in the afternoon: “It’s four o’clock. Smoking jacket hour, man” (4.20). Later, Nate and Chuck argue, Chuck still whiskery in a gray suit and loose red necktie, almost blending into his dim, cave-like suite. “No one understands what [Blair and I] have,” says Chuck.

“No one understands because it’s not normal,” Nate replies.

Chuck pulls himself together to almost ruin Blair’s chances with the prince: to a party at the consulate, he wears a dark suit, white pinstriped shirt, and pink necktie, matching Blair’s blush gown. Later, when Blair stops by his suite to tell him she’s engaged, the tie is loose around his neck. He’s drunk, possessive, convinced that she’s still “his.” Of course, Bart is at the root of it all: “Everything I believed about my father, everything I thought I wanted to be, what I need to be for him, it was all based on lies. The only thing that’s ever been real is me and you.”

Chuck grabs Blair and punches a window; a flying shard cuts her face and she flees. It’s a horrifying scene, the culmination of four years of an unhealthy dynamic; I suspect that the writers didn’t have Chuck hit Blair directly because they still wanted to reunite them.

Indeed, in the finale, Chuck and Blair sleep together as one last goodbye, and Chuck gives his blessing to her engagement. Chuck also learns that Russell was the one who killed Raina’s mother—thus restoring what little admiration Chuck still had for his father.

Season Five

In the premiere, Chuck and Nate have landed in California, where they’re visiting Serena. Vacation Chuck is casual Chuck: a brown leather jacket, ascot, and cargo shirt—almost a little “Henry” from last season. Chuck is still trying to escape himself, this time through daredevil stunts. Since leaving Blair behind, he’s been unable to feel things, and so he rides motorcycles through the winding Hollywood Hills, pays men to beat him up in alleyways. He finally cries when he learns Blair is pregnant—but with Louis’s baby.

His New York wardrobe carries that same sadness: his suits in shades of gray, his signature purple touches “more muted” (“5 Years”). Sometimes, he tops his jackets with Lanvin boutonnieres, perhaps calling back to the last time he wore floral pins, when he was again trying to be “good” Chuck.

Chuck’s impetus for change is not only the loss of Blair but also Dan’s portrayal of him in his first book, Inside. Charlie Trout dies by accidental hanging—with a belt, though Chuck jokes that he’d rather a “shahtoosh scarf, much softer” (5.4). Later in the episode, he confesses to Lily that he doesn’t “want to be the unrepentant bad boy who no one cares lives or dies.” And so, when the opportunity to see a therapist presents itself, he takes it (5.5).

When he meets Dr. Barnes, Chuck is wearing a bright blue suit, pink shirt and pocket square, and blue paisley tie—far from the dull grays he’s been choosing lately, the bright colors more in line with old, “bad” Chuck. Naturally, once he gets to her office, he immediately makes a skeevy comment about never having had sex on a therapist’s couch. The doctor kicks him out, then later reams him for not taking his session seriously: “You never had a childhood and so you behave like a child in the worst ways. You pay for intimacy so you’re always in control and no one can get close to you. Your superficial connections and lack of authentic emotion leave you isolated and alone.” And that’s what you missed on Gossip Girl!

Chuck becomes invested in therapy, even describing a recurring dream to Dr. Barnes (5.6): he keeps trying to reach a beautiful skyscraper (while wearing his “new Berluti wingtips,” he’s careful to note), but the building is forever a block away. Though the meaning of his dream is never properly analyzed, I’m inclined to think that “beautiful building” is meant to be Blair—fitting, considering she was traded for one.

Unbeknownst to Chuck, Dr. Barnes is being paid off by Prince Louis; he hopes she can turn Chuck bad again, thus eliminating any competition for Blair’s heart. Dr. Barnes pushes Chuck, but instead, he “lets go,” offering up the engagement ring he’d been long saving for Blair. By the end of the episode, he leaves the ring box on Harry Winston’s doorstep—a well-intentioned, yet bafflingly naïve, gesture.

Blair even attends a session with Chuck’s second therapist, Dr. Krueger (5.9). She wants to know how to “fix” Louis, now that he is behaving like old Chuck; her bright, accusatory red stands out against the décor. Chuck, on the other hand, fits perfectly in the color palette of the therapist’s office: a gray tweed sports coat, black pants, striped blue shirt, gray tie, and burnt-orange boutonniere—again, a sign of the new, “good” Chuck. “I’ve finally become the man [Blair] wanted,” Chuck later says.

Chuck and Blair run away together in episode ten, but a horrible car accident drives Blair back to Louis, convinced that God saved Chuck in exchange for her marriage. Chuck has no idea why she’s shut him out, and so he descends back into his old scheming ways, having Blair followed by a PI. With this change in behavior comes a change in wardrobe: a gray plaid blazer with a blue shirt and gray ascot, neckwear more commonly seen in seasons one and two.

Chuck tries to stop Blair from marrying Louis; to her wedding, he wears a navy pinstriped suit, navy polka dot tie, pale blue shirt, and, yet again, a blue boutonniere. Still, Blair holds firm even as “good” Chuck, marked by his little flower, stands before her.

When her marriage to Louis falls apart, Blair turns to Dan instead of Chuck—much to Chuck’s fury. He tries to ruin Dan’s book proposal, gifts his literary agent a shahtoosh scarf, a cheeky nod at Charlie Trout. His actions even cost Blair her dowry—a sum that would’ve bankrupted the Waldorfs and nearly bankrupts him—all in the name of convincing everyone that Dan is the “real villain” and not him.

In episode eighteen, the long-absent banker’s collar returns, hinting at the impending homecoming of an old character: Bart himself. His father reappears in episode twenty-three; he faked his death, he tells Chuck, because a business rival was threatening to hurt him and his family. Chuck takes down the rival, and his father is free to return to the world of the living—and finally give Chuck a tiny scrap of approval: “The way you took control, got me out of this mess, makes me think I did something right in raising you,” says Bart.

In this scene, Chuck wears a blue-checked banker’s collar shirt, blue tie, mustard pocket square, and black suit—imitating Bart’s usual shades of blue. Their unity, however, is short-lived. In the season finale, Bart convinces Chuck to make a “grand romantic gesture” to Blair: “No one does [one] better than a Bass.” Bart even gets the Harry Winston ring back and gives it to Chuck.

Chuck is dressed in a gray suit with a purple shirt, pocket square, and necktie. Purple, of course, is Chuck’s signature, but the color is also reminiscent of Chuck’s mother and father, the words Evelyn spoke in season three: “Bart was always playing with people’s heads.” Bart is playing another mind game with Chuck, the ring a test to see if Chuck is “ready to be a Bass, to do the things [he needs] to do to be a great man.”

By taking the ring and choosing his love for Blair, Chuck fails the test. In Bart’s mind, Chuck’s business is always hindered by Blair: “You didn’t try and trade her for a hotel deal? You didn’t let everything fall apart when you ran away from her all the way to Europe? You didn’t, just three months ago, almost bankrupt yourself trying to get her out of her marriage?”

Chuck absorbs his father’s words and then throws them back in Blair’s face. “The only reason Waldorf Designs has a future is because I gave mine up for it,” he tells her. “I always put you first and you bet against me every time.”

The next day, Chuck is back to his dandy self in a blue plaid shirt, pink ascot and pocket square, and blue blazer—no more banker’s collars for him. He teams up with Uncle Jack to take down Bart, and they’re off to Monte Carlo to gamble their way to victory. Blair arrives at the casino unexpectedly, tells Chuck she’s “all in”—as if he’s right and she never was before. What about trading herself for a hotel? What about taking care of him at the funeral?

Why is the show treating the words of Bart Bass—the villain, the hardest motherfucker in real estate—like they’re gospel? 

Season Six

Sadly, the final season doesn’t concern itself with answering these questions. Rather, the show focuses on turning Chuck into the hero, Dan into the villain, and Bart into . . . I don’t know, Satan? To quote Nate in episode seven, “Who would’ve thought Chuck Bass would’ve turned out to be the good guy and Dan the villain?”

Blair wears Chuck’s engagement ring on a chain around her neck; Chuck has promised to put it on her finger once he defeats his father. “You are a distraction,” Chuck reasons, “because when we’re together, you’re all that I think about. And I would give up my empire for you, I would give up everything for you. . . .  It’s the boy who blames the girl, not the man, and that’s what I want to be with you.” I think calling someone a distraction and withholding love is a form of blame, but what do I know? After almost six years, the logic of Chuck and Blair’s relationship has become so manipulated and warped that the reasons they can’t be together no longer make sense.

Chuck’s costuming in the last season is similarly scattered. One episode, he’s in a plaid blazer; the next, a pinstriped suit or a floral pin. He’s jumping between eras like he’s Taylor Swift in the “Look What You Made Me Do” music video, pulling different influences and go-tos from previous seasons. Perhaps this is supposed to be a holistic Chuck, not “good” or “bad” but whole.

Of course, Chuck still knows the importance of color. He wears his power purple when he’s at his best, helping an exhausted Blair put on her first runway show with Waldorf Designs. For a horse show in episode four, he chooses Kentucky Derby–ready pastels: a pink flower pin, tan blazer, brown pants, pink checked shirt, and green bowtie. Why a horse show? Well, Bart used a horse purchase (the aforementioned Arabians, I suppose) as a cover for an illegal oil trade with a Sudanese businessman. He didn’t fake his death to save Chuck and Lily; he did it to save himself from federal prison.

Chuck tries to get proof of the deal, but Bart evades every move, turns even Lily against Chuck. “The only parent who ever loved me, the mother who chose me as a son, abandoned me,” Chuck tells Blair, who’s coming off the success of her capsule collection (6.7). Just like last season, Chuck can’t bear the idea of leaving behind his future for Blair’s. They can’t be together, he says: “You fulfilled your side [of our agreement]. I failed at mine.”

So returns “dark” Chuck in his black robe (6.8). Only once he convinces Lily that Bart is, indeed, evil does he turn back to bright color: in episode nine, he wears a bold purple shirt and paisley tie with a magenta flower pin, matching Blair’s beret.

The final Chuck-Bart showdown comes at the end of this episode. Bart tried to crash Chuck in the Bass jet, and Chuck is understandably upset about that. Father and son stand off on the rooftop, Chuck summarizing his grievances of the last five seasons: “You’re not a man. A man accepts responsibility for his actions. A man takes care of his family. A man doesn’t pay a mother to abandon her child and then tell that child his mother is dead. A man doesn’t try to have his own son killed!” While Chuck is in a simple tux, Bart is dressed like the steeliest of businessmen: gray pinstriped suit, gray tie, gray banker’s collar shirt.

They tussle as Blair watches in horror, and Bart accidentally falls off the side of the roof. He catches the railing, then begs Chuck to save him. It’s like The Lion King if both of them were Scar! Chuck and Blair make no move to help Bart, and he falls to his death. To avoid having to testify against each other, Chuck and Blair finally get married, in matching pale blues and whites.

Flash-forward five years, to Serena and Dan’s wedding, and Chuck and Blair have a toddler-age son, Henry. Yes, that’s right, they named him Henry, after Chuck’s fake identity. Henry is a mini Chuck in a purple striped shirt and bowtie, black three-piece suit, and purple boutonniere.

Chuck himself wears a navy pinstriped suit with blue striped shirt, blue ascot, and gold boutonniere. The double-breasted cut of the jacket is a little more mature—not a style he wore frequently as a younger man—but the rest of his outfit is reminiscent of seasons past. After all, this moment is meant to be a culmination—after years of his rocky relationship with his own father, Chuck can finally be a good father to his own son. And yet, Henry’s name and outfit tie him completely to Chuck; he carries no hint of Blair, save perhaps for the bow. For that’s forever the problem with a romantic antihero—their backstory will always subsume the heroine.

[My last profile—Blair Waldorf’s—will publish on Thursday, 6/3.]

DP on GG

My partner, Daniel, spent 2020 overhearing episodes of Gossip Girl from various rooms of our apartment. He still doesn’t understand the show and he doesn’t care.

DP: They’re teenagers. They should just go to the sodey fountain. Get a malted and then go home and touch yourself.

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Filiberto Hargett

Update: 2024-12-03