Characterization
Denise Martin of the Los Angeles Times characterizes him as "a would-be Casanova than a seasoned predator. He's the charming devil at the center of all the intrigues, the go-to guy when something naughty needs to be said and he's the most self-aware of the Upper East Side high schoolers.
Stephanie Savage, one of the television series' creators, described him as "entertaining and observationally smart, he's the friend who says all the things you want to say but can't, and he tempts you in ways, at that age, you want to be tempted." She compared his relationship with Blair to Glenn Close and John Malkovich's in Dangerous Liaisons. She found Westwick's portrayal of Chuck was similar to James Spader of Pretty in Pink and Robert Downey, Jr..
Savage said about the character's evolution during the six seasons: "I feel like Chuck has gone on the biggest journey of any one on the show. In the pilot, he's pretty much a pure villain. He's not a character that has a lot of layers. That was something Ed Westwick really brought as an actor. And his chemistry with Leighton — when we saw them together on screen and the power of the two of them working together but also being attracted to each other, which really inspired us to grow that character and give him some more layers."
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