Favorite Silent Hill Game: Silent Hill 4
Least Favorite Silent Hill Game: Silent Hill
Favorite Silent Hill Soundtrack: Silent Hill 3 Rip ^^
Favorite Main Protagonist: Henry Townshend
Favorite Main Antagonist: Walter Sullivan
Favorite Supporting Character: The dead guy at the end of that alley in SH2
Favorite Monster/Enemy: Origins' Remnant
Scariest Monster/Enemy: Silent Hill's Doctor
Favorite Weapon: A pair of Travis' bare manly hands
Favorite Location/Room: Apartments in SH4 apartment building
Favorite Cutscene: A flying bed in Silent hill 2 :O
Favorite Quote: "Eddie, have you gone nuts?"... it's freakin' hilarious.

Favorite Silent Hill game: Silent Hill 1
Least Favorite Silent Hill Game: I don't have one!
Favorite Silent Hill soundtrack: Silent Hill 3.
Favorite Main Protagonist:Harry Mason
Favorite Main Antagonist: Walter Sullivan
Favorite Supporting Character: Douglas Cartland or Richard Braintree
Favorite Monster/Enemy: Pyramid Head!
Scariest Monster/Enemy: Grey Children
Favorite Weapon: Emergency Hammer!
Favorite Location/Room: Brookhaven Hospital
Favorite Cutscene:The scene where you meet Kaufman for the first time.
Favorite Quote: "Have you seen a little girl?"

Favorite Silent Hill game: SH2
Least Favorite Silent Hill Game: None, but for the sake of the post I'll choose Shattered Memories as it's not as scary as the rest, but I still love it
Favorite Silent Hill soundtrack: SH2
Favorite Main Protagonist: James Sunderland
Favorite Main Antagonist: Pyramid Head
Favorite Supporting Character: Angela Orosco
Favorite Monster/Enemy: Flesh Lips (very bizarre appearance and choice of weapons!)
Scariest Monster/Enemy: Either Insane Cancer from SH3 or the Patients from SH4 (the speed and size of both monsters caused me to panic, loved it)
Favorite Weapon: the Great Knife or the Maul
Favorite Location/Room: Brookhaven Hospital transformed, after James gets pushed off the roof by P.Head (the new atmosphere was even darker than what it already was and the music was chilling, amazing)
Favorite Cutscene: When Walter Sullivan first attacks you or Vincents cruel 'They look like monsters to you?!' joke.

I can't remember the last time I did this, it may have been on my old account, anyway I don't know how much my answers have changed but I know some have.

Fav Game: SH2 (followed closely by 1)
Least Fav Game: Homecoming
Fav Soundtrack: In game: 2, On CD: 3
Fav Protagonist: James (nice jacket)
Fav Antagonist: Pyramid Head
Fav Support Char: Laura (my favorite game character period)
Fav Enemy: Duo Pyramid Head (also love sh1 ghost babies)
Scar Enemy: Giant Lizard
Fav Weapon: Handgun
Fav Location: Labyrith
Fav Cutscene: James watches the video
Fav Quote: "You killer! Why'd you do it, I hate you! I want her back, give her back to me! I hate you James! I hate you, I hate you, I hate you!" and "Leave her alone! Leave us both the hell alone!"
Fav Graphics: SH2
Fav Ending: Leave, SH2
Fav Sound: Picking up item in SH2, especially when you find a lot at once

Sorry, felt like adding a few :p

Why have I not noticed this thread before Anyway..

Favorite Silent Hill game: Silent Hill 2
Least Favorite Silent Hill Game: Shattered Memories
Favorite Silent Hill soundtrack: Silent Hill 3
Favorite Main Protagonist: Tied between James and Alex, and then Heather...
Favorite Main Antagonist: Maria
Favorite Supporting Character: Angela
Favorite Monster/Enemy: Enemy -> Closer, Boss -> Maria Demon
Scariest Monster/Enemy: Enemy -> Scraper, Boss -> Leonard
Favorite Weapon: Emergency Hammer
Favorite Location/Room: Pretty much all the "nowhere" locations from 1,2 and 3.
Favorite Cutscene: Fiery Staircase, so sad watching Angela disappear up the stairs knowing you can't help her.
Favorite Quote: Can't remember. I suppose most of the things Heather says when examining things.

Favorite Silent Hill game: 2
Least Favorite Silent Hill Game: 4
Favorite Silent Hill soundtrack: 2
Favorite Main Protagonist: Heather
Favorite Main Antagonist: Pyramind Head
Favorite Supporting Character:
Favorite Monster/Enemy: Lying Figure
Scariest Monster/Enemy: Invisible Thing In Prison
Favorite Weapon: Lead Pipe
Favorite Location/Room: Heavens Night
Favorite Cutscene: SH3 Car Scene
Favorite Quote: "Monsters? They looked like monsters to you?"

Mind that I play only 2, 3 and 4.

Favorite Silent Hill game: 2
Least Favorite Silent Hill Game: 4
Favorite Silent Hill soundtrack: 2
Favorite Main Protagonist: Heather (she is a great developed character)
Favorite Main Antagonist: Pyramind Head
Favorite Supporting Character: Eileen
Favorite Monster/Enemy: Numb bodies. They aren't just cute, they are smart too.
Scariest Monster/Enemy: Abstract Daddy (boss and regular enemies)
Favorite Weapon: Chain saw (from SH 2. Awkward, but powerful )
Favorite Location/Room: Lakeview Hotel, after play the VCR.
Favorite Cutscene: Angela last cutscene (staircase).
Favorite Quote: " But you know what? It doesn't matter if you're smart, dumb, ugly, pretty... it's all the same once you are dead... and a corpse can't laugh." - Eddie Dombrowski

Favorite Silent Hill game: Silent Hill 3
Least Favorite Silent Hill Game: Silent Hill: Shattered Memories
Favorite Silent Hill soundtrack: Silent Hill 3
Favorite Main Protagonist: Heather Mason/Harry Mason (can't decide)
Favorite Main Antagonist: Claudia Wolf
Favorite Supporting Character: Maria
Favorite Monster/Enemy: Closer
Scariest Monster/Enemy: Twin Victims
Favorite Weapon: Laser Beam and Sexy Beam (c'mon! It IS cool)
Favorite Location/Room: Silent Hill 2's Hospital. Silent Hill's Nowhere. (once again, can't decide)
Favorite Cutscene: "Long car ride into Silent Hill" - Silent Hill 3.
Favorite Quote: "In my restless dreams, I see that town... Silent Hill."

Favorite Silent Hill game: SH3 and SH:SM
Least Favorite Silent Hill Game: SH4
Favorite Silent Hill soundtrack: SH2
Favorite Main Protagonist: Heather, Harry, James
Favorite Main Antagonist: Claudia
Favorite Supporting Character: Angela
Favorite Monster/Enemy: Abstract daddy
Scariest Monster/Enemy: Scarlet and schisms
Favorite Weapon: flame thrower
Favorite Location/Room: amusement park
Favorite Cutscene: Stairs o fire
Favorite Quote: "I'm lonely and horny... isn't that when you always turn up? "-dahlia SH:SM

Favorite Silent Hill game: Silent Hill 2
Least Favorite Silent Hill Game: Hmmm nothing I liked them all
Favorite Silent Hill soundtrack: Silent Hill 3
Favorite Main Protagonist: James, Harry, Heather
Favorite Main Antagonist: Pyramind Head
Favorite Monster/Enemy: Pyramid Head or Nurses
Scariest Monster/Enemy: Invisible Thing In Prison Courtyward
Favorite Weapon: Chainsaw
Favorite Location/Room: Brookhaven Hospital
Favorite Quote: "Have you seen a little girl?, Short black hair?"

Favorite Silent Hill game: SH/SH 2//SH3/SH 4 and Origins cause of Travis
Least Favorite Silent Hill Game: None
Favorite Silent Hill soundtrack: SH 1
Favorite Main Protagonist: Henry Townshend, he's gangster/James/Travis
Favorite Main Antagonist: Dahlia.... She cracks me up lol. The Time Is Neigh!!!
Favorite Supporting Character: Alessa I suppose in Origins, (If she is supporting)
Favorite Monster/Enemy: Scarlet!
Scariest Monster/Enemy: Pyramid Head raping mannequins is creepy
Favorite Weapon: Alien Tesla Rifle for Travis lololol.
Favorite Location/Room: Riverside Motel
Favorite Cutscene: Mary Boss, when she turns into that monster
Favorite Quote: "Are you yearning for that special place to spend quality time with your loved one? Do you need to relax and get away from it all? Come to Silent Hill for the ultimate peaceful getaway" - SH 4 Radio
^ that is such a lie, a total Troll radio station lol. Silent Hill is no place for a vacation, unless you enjoy Pyramid Head and his "little pyramid head" and blood on the walls and monsters attacking you, and girls giving birth to demon gods, and being locked from the inside in your room.

Also, "They're all crazy" - Travis Grady

I've found my Favorite Side Character because I just finished SH3.

Father Vincent was an awesome character and presented a nicer look at The Order. The Order is not made up of Claudia's and Dahlia's and the other fanatics. No, thre are people in The Order - good, sane people. (though Vincent probably wasn't that "good")

I loved how he constantly called out Claudia for being a lunatic and at the end, pointed out what was obvious to the player.
"You think that this is the work of God? Isn't this nothing more than your own personal nightmare?"

Vincent has faith but he is not consumed by that faith. He has enough self-interest to keep him sane.

Plus, who can't appreciate a heaping helping of smugness? Vincent had it oozing out of his pores.

Don't worry, Father. I'll cry over your grave. I'm sorry that Heather was a bitch and stood by and watched you get murdered. I'm sure there's a law against that and someone should probably arrest her.

Favorite Silent Hill game: Silent Hill 3
Least Favorite Silent Hill Game: Silent Hill: Shattered Memories or Origins.
Favorite Silent Hill soundtrack: Silent Hill 2
Favorite Main Protagonist: Alessa Gillespie.
Favorite Main Antagonist: I would consider him neutral, but Vincent.
Favorite Supporting Character: Cybil Bennett.
Favorite Monster/Enemy: Memory of Alessa, Nurses, Numb Bodies, Pyramid Head, Eddie.
Scariest Monster/Enemy: Dogs, Slurpers, Mumblers, Grey Children, and Rompers, and by scariest, I mean most aggravating.
Favorite Weapon: Katana or Steel pipe.
Favorite Location/Room: Hospital Storage room.
Favorite Cutscene: Probably the one that corresponds with the first quote listed below.
Favorite Quote: "Shut your stinkin' mouth, bitch!", "There's no mail here, not even from a dead wife. Well, it's not like I have one of those anyway.", "Listen, suffering is a fact of life, either you learn that or you go under."

Favorite Silent Hill game: SH: Homecoming
Least Favorite Silent Hill Game: SH4
Favorite Silent Hill soundtrack: SH2
Favorite Main Protagonist: Alex Shepherd
Favorite Main Antagonist: Walter Sullivan
Favorite Supporitng Character: Lisa Garland
Favorite Monster/Enemy: Pyramid Head
Scariest Monster/Enemy: Scarlet Fitch
Favorite Weapon: Chainsaw
Favorite Location/Room: Hell Decent
Favorite Cutscene: When Alex walks in on Dr. Fitch in Hell Decent
Favorite Quote: "I'm here for you, James. See? I'm real."

Favorite Silent Hill Game: Silent Hill 2
Least Favorite Silent Hill Game: Homecoming
Favorite Silent Hill Soundtrack: Silent Hill 2
Favorite Main Protagonist: James
Favorite Main Antagonist: P-Head
Favorite Supporting Character: Eddie
Favorite Monster/Enemy: what ever the 2 headed thing in 4 was
Scariest Monster/Enemy: P-head in the apartment fight, just because it's so tense
Favorite Weapon: Moon gauntlets in origins
Favorite Location/Room: henry's apartment when the crazy shit starts happening
Favorite Cutscene: Eddie's falling out
Favorite Quote: "thanks"-James. it's not so much the quote but the way it is said

This one's refreshing 'cause I never really thought about most of them.

Favorite Silent Hill game: SH2
Least Favorite Silent Hill Game: SH Homecoming
Favorite Silent Hill soundtrack: SH2
Favorite Main Protagonist: none
Favorite Main Antagonist: Claudia or Walter
Favorite Supporting Character: Maria
Favorite Monster/Enemy: Raw Shock
Scariest Monster/Enemy: Closer
Favorite Weapon: steel pipe
Favorite Location/Room: Lakeview Hotel / Room 312
Favorite Cutscene: -Restaurant "Lake Shore"- cutscene
FavoriteQuote: "James, where are you? I'm waiting, I'm waiting for you. Please come to me. Do you hate me? Is that why you won't come?"

Favorite Silent Hill game: Silent Hill
Least Favorite Silent Hill Game: Silent Hill Homecoming
Favorite Silent Hill soundtrack: Silent Hill 2
Favorite Main Protagonist: Harry
Favorite Main Antagonist: Pyramid Head
Favorite Supporting Character: Valtiel
Favorite Monster/Enemy: Lying Figure
Scariest Monster/Enemy: Pendulum
Favorite Weapon: Steel Pipe
Favorite Location/Room: The final descent in one of the first two games (not sure which I prefer)
Favorite Cutscene: When Lisa discovers what she is in the first game. So sad, so powerful.
Favorite Quote: "I got a letter, the name on the envelope said, Mary. It can't be, that's what I keep telling myself, a dead person can't write letters." I get chills everytime I start a new game...

Now that I've replayed every game in the series a couple more times, I've decided to change my list:

Favorite Silent Hill game: SH2/Origins/Homecoming (still can't decide between the three)
Least Favorite Silent Hill Game: SH3 (used to be 4, but The Room grew on me recently)
Favorite Silent Hill soundtrack: SH: Homecoming/SH: Shattered Memories
Favorite Main Protagonist: James Sunderland/Travis Grady
Favorite Main Antagonist: Walter Sullivan
Favorite Supporitng Character: Elle Holloway
Favorite Monster/Enemy: Lurker
Scariest Monster/Enemy: Twin Victims/Grey Children
Favorite Weapon: Shotgun
Favorite Location/Room: Riverside Motel
Favorite Cutscene: Travis remembers his father's fate
Favorite Quote: "You can't just kill someone because of the way they looked at you."

Favorite Silent Hill game: Silent Hill 3
Least Favorite Silent Hill Game: Homecoming
Favorite Silent Hill soundtrack: SH3/Homecoming/Origins/SH2
Favorite Main Protagonist: Heather Mason/Travis Grady
Favorite Main Antagonist: Claudia
Favorite Supporting Character: Maria
Favorite Monster/Enemy: Closer
Scariest Monster/Enemy: The ghosts from SH4 -_-
Favorite Weapon: Maul/
Favorite Location/Room: Heather's House
Favorite Cutscene: The scene where Heather finds Harry dead/ When James meets Laura outside in the fog
Favorite Quote: "I wish only for the salvation of mankind..But for that to happen, the world must first be remade."

Favorite Silent Hill game: SH2
Least Favorite Silent Hill Game: SH4 (I still like it a lot. Haven't played Homecoming, BTW)
Favorite Silent Hill soundtrack: SH1, but Laura's Theme is the best track ever.
Favorite Main Protagonist: James, even though he's effing stupid.
Favorite Main Antagonist: Walter
Favorite Supporting Character: Cybill
Favorite Monster/Enemy: PH, no contest
Scariest Monster/Enemy: Teddy Bears in the sewers. How their cyclopean-face jerked while they approached me gave me the chills.
Favorite Weapon: Big knife!
Favorite Location/Room: SH3's Hospital especially the room with the mirror.
Favorite Cutscene: Lisa's realization that she's 'one of them' and subsequent cinematic.
Favorite Quote: "The old gods haven't left this place and they still grant power to those venerate them. Power to defy even death..." Eeek!