Screenplays Ranked

Best Overall Nominees: 2007 or 2004. Or 2001. The writers branch usually knows what its doing.
Best Original Lineup: 2004 & 2001 - I'd include 2002 if it weren't for that piece of shit Greek Wedding. 2008 is solid, too. The Original nominees are usually a tad better than the adapted. I think going into the season you can usually pick the adapted nominees a little easier sight unseen whereas Original can produce more deserving surprises.
Best Adapted Lineup: 2007 - 2006 & 2004 (swap Neverland for Mean Girls and that category would be awesome) are close.
Worst Original Lineup: Probably 2005.
Worst Adapted Lineup: 2008. Easy.

Best Winning Duo: 2004 - Eternal Sunshine and Sideways. Remember how that year it was those two pitted against each other in the critics awards and Sideways won the vast majority of them? Us Eternal fans said we'd be in the right a few years down the line. We were right. Though, I'm kinda bummed Alexander Payne still hasn't made a movie since.

2009:
Original:
1. Inglourious Basterds
2. The Hurt Locker***
3. The Messenger
4. A Serious Man
5. Up

Adapted:
1. In the Loop
2. Up in the Air
3. District 9
4. Precious***
5. An Education

2008:
Original:
1. In Bruges
2. Happy-Go-Lucky
3. Milk***
4. Frozen River
5. Wall-E

Adapted:
1. Slumdog Millionaire***
2. The Reader
3. Doubt
4. Frost/Nixon
5. The Curious Case of Benjamin Button

2007:
Original:
1. Lars and the Real Girl
2. The Savages
3. Juno***
4. Ratatouille
5. Michael Clayton

Adapted:
1. No Country for Old Men***
2. Atonement
3. The Diving Bell and the Butterfly
4. There Will Be Blood
5. Away From Her

2006:
Original:
1. The Queen
2. Pan's Labyrinth
3. Little Miss Sunshine***
4. Babel
NS: Letters From Iwo Jima

Adapted:
1. The Departed***
2. Children of Men
3. Notes on a Scandal
4. Little Children
5. Borat

2005:
Original:
1. Good Night and Good Luck
2. Match Point
3. The Squid and the Whale
4. Crash***
5. Syriana

Adapted:
1. Brokeback Mountain***
2. Capote
3. The Constant Gardener
4. A History of Violence
5. Munich

2004:
Original:
1. Eternal Sunshine of the Spotless Mind***
2. Vera Drake
3. The Aviator
4. Hotel Rwanda
5. The Incredibles

Adapted:
1. Before Sunset
2. The Motorcycle Diaries
3. Sideways***
4. Million Dollar Baby
5. Finding Neverland

2003:
Original:
1. Lost In Translation***
2. Finding Nemo
3. In America
NS: The Barbarian Invasions, Dirty Pretty Things

Adapted:
1. American Splendor
2. Mystic River
3. Seabiscuit
NS: Lord of the Rings: Return of the King***, City of God

2002:
Original:
1. Y Tu Mama Tambien
2. Talk to Her***
3. Far From Heaven
4. Gangs of New York
5. My Big Fat Greek Wedding

Adapted:
1. Adaptation
2. The Pianist***
3. The Hours
4. Chicago
5. About A Boy

2001:
Original:
1. The Royal Tenenbaums
2. Gosford Park***
3. Amelie
4. Monster's Ball
5. Memento

Adapted:
1. Ghost World
2. In the Bedroom
3. Shrek
4. Lord of the Rings: The Fellowship of the Ring
5. A Beautiful Mind***

2000:
Original:
1. You Can Count on Me
2. Almost Famous***
3. Erin Brockovich
NS: Billy Elliot, Gladitoar

Adapted:
1. Traffic***
2. Wonder Boys
3. Crouching Tiger, Hidden Dragon
4. O Brother Where Art Thou
5. Chocolat