These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Alternative Character Interpretation: In Curse: Did Tiffany send Chucky to Andy on his orders alone or was she still pissed off about the events of Seed that she sent him knowing Andy would be ready for him.
Complete Monster: Charles Lee Ray, later known as the killer doll Chucky, was a notorious Serial Killer when alive, and in death has used Hollywood Voodoo to possess a doll to escape his fate. Chucky proceeds to murder his owner's babysitter because she annoys him, and hunts down, tortures and murders his old voodoo teacher to get information on how to become human again before trying to tear out his ten year old owner's soul and possess him. Throughout the films, Chucky commits many more murders for his own amusement and replaces blanks with real ammo at a military camp war games training solely to enjoy the chaos. Even when the films briefly turned comedic, Chucky remained heartless as ever, murdering his own wife when she tried to leave him, with no remorse. When Curse of Chucky brought the series back to horror, Chucky sends himself to unsuspecting families to destroy them and was revealed, as Charles Lee Ray, to have even stabbed a pregnant woman to cripple her unborn daughter after she rejected his advances. Despite his sense of humor, Chucky has always remained a sadistic, murderous monster and has only grown worse over time.
Canon Discontinuity: Averted with Curse Of Chucky. At first it seems to take place after Child's Play 3, but then come's the attic scene....
Harsher in Hindsight: In the first one, Chucky tells the witch doctor he has a date with a 6 year old boy. Then? Creepy because he's a murderous doll. Now? With all the pedophile stories coming to light, it sounds even worse.
Hilarious in Hindsight: Seed of Chucky features Hannah Spearitt working on a film set as a PA for actors, one of whom includes Jason Flemyng. Fast forward a few years where Hannah would again be working for Jason on Primeval.
Magnificent Bastard: When he dropped the Villain Ball, Chucky sure had no problem playing everyone like a fiddle in Child's Play 3. Up to, and including, him arranging for the Red Team to shoot members of the Blue Team to death, and attempting to blow them all up in the ensuing chaos. Would have gotten away with it had it not been for a Heroic Sacrifice by one of the supporting characters.
Then Chucky was hovering over the horizon for a long time due to the fact that he has been trying to get a human body. But, the rule is to take possession of the human that you first introduce yourself too, regardless. Nothing personal. Just a rule. Trying to kill him was also just another Kick the Dog moment he had. The one chance he could've redeemed himself was to stop killing once he found out that he had a son and daughter. Instead, he changed his mind and decided to stay as a doll. This causes Tiffany to leave him because of that. Therefore, he finally crossed it in when he murdered Tiffany for leaving him.
Narm: In the 1980s, Charles Lee Ray's long black hair, black suit and black trenchcoat look was fine and dandy. In the post-The Room world, the return of this look in Curse of Chucky has the potential to lead to a bit of momentary confusion, as Dourif in the get-up now heavily resembles the infamous Tommy Wiseau.
One-Scene Wonder: Andy in The Stinger of "Curse of Chucky". Just look at the sheer number of tropes for it, at least one per page and far more on the main one than the rest of the film.
To explain this, he is a little kid who lives at the Millitary School and constantly gets special privileges. He also knows Chucky is alive and believes literally everything Chucky tells him, and refuses to listen to Andy's warnings claiming he jealous of his and Chucky's friendship.
Uncanny Valley: The Chucky doll itself is just as unsettling when it's not moving around or acting sentient. But compared to Tiffany, Chucky looks normal.
The extendedending of the second film takes it Up to Eleven. We see Chucky's head and head alone reconstructed, no eyes, empty, undetailed mouth. It sits there for a moment, and then smiles to remind us that Chucky won't stay dead.