Child’s Play 2: Number one was close. The original is a better movie overall as suspense is slowly developed while Chucky is kept off-screen for almost half of the running time. But the first sequel features far more of Chucky doing what he does best, disposing of people in brutal fashion. He’s a mean killing machine. The Chucky doll effects are better as well.
Child's Play: While it takes him awhile to show up, when he does, Chucky makes the wait worth it. It’s impressive how freaky a small killer doll actually is. Chucky is menacing and bloodthirsty, and a potent reminder of how creepy a kid’s plaything can be.
Curse of Chuck: 2013’s direct-to-DVD entry gave Chucky new life. The jokes are left behind and Chucky is back to being frightening again. There’s some serious gore and nasty kills along with decent tension in the reboot, and it’s refreshing to see the character treated as something to fear.
Child's Play 3: Easily the weakest of the entire series in terms of quality as the military school setting isn’t taken full advantage of. It plays out like a lazy cash-in more than anything and Chucky isn’t very scary (there are a lot of one-liners and the tone is more jokey, less horror) and a lot of time is spent with teenage Andy and a superior officer at the school. He’s still capable of spilling blood, but at this point Chucky is veering pretty far from his roots.
Bride of Chucky: Chucky had been missing from the big screen for 7 years prior to the release of 1998’s Bride of Chucky. While it’s a hell of a lot of fun and at times ridiculously bloody, the fourth entry takes a far more comedic route. Chucky spends a significant amount of time cracking wife and bickering with his lady/doll, Tiffany. There’s little attempt to make him scary, though he remains capable of offing people in gruesome ways.
Seed of Chucky: If Bride took Chucky in a more overtly comedic direction, the fifth movie in the series is an out-and-out comedy (that doesn’t skimp on the gore). It’s mostly "Chucky and Family" squabbling along with potshots at and references to Hollywood/celebrity culture. It’s not without its moments, but we are a very long way from the Chucky of the first two movies in this one. Chucky isn’t menacing or creepy at all. He’s a Jerry Springer character.