After giving it about an hour's thought, these are my top five titles for each season of 2000 to 2009. Top tens for seasons that made decisions hard for me.

Winter 2000
Boogiepop Phantom
Kazemakase Tsukikage Ran
Okamajo Doremi #
Miami Guns
Megami Kouhosei

Easy choices for me. This wasn't a great season for anime by any means.

Spring 2000
Furi Kuri
Banner of the Stars
NieA_7
Gatekeepers
Ayashi no Ceres

Summer 2000
Strange Dawn
Jin-Roh
Brigadoon - Marin to Meran
Card Captor Sakura Movie 2
Hand Maid May

Another bitzer season, this one.

Fall 2000
VanDread
Sci Fi Harry
Argento Soma
Blood - The Last Vampire
Yami no Matsuei

Winter 2001
Maetel Legend
Shin Getter vs Neo Getter
Time Stranger Kyoko
Earth Girl Arjuna
Motto Ojamajo Doremi

Pretty bog-standard season, this one.

Spring 2001
Jungle wa Itsumo Hale nochi Guu
Read Or Die
Figure 17 - Tsubasa and Hikaru
Super GALS Kotobuki Ran
Animation Runner Kuromi-chan
Noir
You're Under Arrest 2
Mahou Senshi Louie
Angelic Layer
Puni Puni Poemi

But it got better.

Summer 2001
Fruits Basket
Scryed
Banner of the Stars 2
Spirited Away
Alien 9

Fall 2001
Cowboy Bebop Movie
Chiyoko Millennial Actress
Hellsing
Kaze no Yojimbo
Hikaru no Go

Winter 2002
Fullmetal Panic!
Rah-Xephon
Onegai Teacher
Hoshi no Koe
Secret of Cerulean Sand

Spring 2002
Azumanga Daioh
Abenobashi Mahou Shoutengai
12 Kingdoms
WXIII Patlabor the Movie 3
Chobits

Summer 2002
Princess Tutu
The Cat Returns
SaiKano
Witch Hunter Robin
Yukikaze

Fall 2002
Haibane Renmei
Ghost in the Shell: Stand Alone Complex
Gundam Seed
Kiddy Grade
Overman King Gainer

Things were really easy to choose at about this point. It started getting harder from here on.

Winter 2003
Yokohama Kaidashi Kikou: Quiet Country Cafe
Mahou Tsukai no Taisetsu na Koto - Someday's Dreamers
Macross Zero
Gunparade March
Wolf's Rain

Spring 2003
Kino no Tabi: The Beautiful World
Scrapped Princess
Texhnolyze
Stellvia of the Universe
Kaleido Star
Last Exile
GadGuard
Hitsuji no Uta
Matantei Loki Ragnarok
Mermaid Melody Pichi Pichi Pitch

Summer 2003
Fullmetal Panic? Fumoffu
Tokyo Godfathers
NaruTaru
Nasu: Summer in Andalusia
Da Capo

Fall 2003
Planetes
R.O.D. the TV
Fullmetal Alchemist
Gunslinger Girl
Uninhabited Planet Survive

Winter 2004
Paranoia Agent
Maria-sama ga Miteru
Gokusen
Jubei-chan 2 - The Revenge of Siberia Yagyuu
Futari wa Precure

Spring 2004
Samurai Champloo
Monster
Mahou Shoujotai Alice
Innocence
Kenran Butou Sai - The Mars Daybreak

Summer 2004
Kurau Phantom Memory
Maria-sama ga Miteru Haru
Soukyuu no Fafner
Otogizoushi
Elfen Lied

It says how bad this past season was that Elfen Lied got into my top five.

Fall 2004
Gankutsuou
Fantastic Children
Beck
Genshiken
Beyond The Clouds
Windy Tales
Howl's Moving Castle
Mai-Hime
Rozen Maiden
School Rumble

Winter 2005
Starship Operators
Kino no Tabi - Life Goes On
Mahoraba
Shin Angyou Onshi
Ah My Goddess

Spring 2005
Zettai Shonen
Eureka Seven
Honey and Clover
Victorian Romance Emma
Basilisk

Summer 2005
Kamichu
Pani Poni Dash
Fullmetal Panic - The Second Raid
Ichigo Mashimaro
Okusama wa Mahou Shoujo

Fall 2005
Mushishi
Aria the Animation
Noein
Jigoku Shoujo
Magical Girl Lyrical Nanoha A's
Akagi
Mai-Otome
Paradise Kiss
Shakugan no Shana
Blood+

This was the "holyfarkingshite where did all these shows suddenly come from" season.

Winter 2006
Hellsing Ultimate
Pale Cocoon
Ergo Proxy
Rec
Kashimashi

And then it went quiet, again. After Kashimashi, the quality really dropped off.

Spring 2006
Higurashi no Naku Koro ni
The Melancholy of Haruhi Suzumiya
Aria the Natural
Black Lagoon
Simoun
xxx-HOLiC
Ouran High School Host Club
Saiunkoku Monogatari
School Rumble Ni Gakki
Strawberry Panic

The heart of 2006, for sure. Why I remember the year so fondly.

Summer 2006
The Girl Who Leapt Through Time
Welcome to the NHK
Honey and Clover II
Le Chevalier D'Eon
Kemonozume

Fall 2006
Code Geass
Black Lagoon: The Second Barrage
Death Note
Ghost Hunt
Soukou no Strain
Asatte no Houko
Paprika
Freedom
Maria-sama ga Miteru 3rd Season
Kanon

I keep saying: it isn't that Death Note is bad, it's just that its fans are zurückgeblieben.... Like narutard zurückgeblieben. You can't help but associate it with the worst aspects of fandom.

Winter 2007
Nodame Cantabile
Hidamari Sketch
5cm per Second
Rozen Maiden Ouverture
Manabi Straight

Spring 2007
Seirei no Moribito
Tengen Toppa Gurren Lagann
Lucky Star
Dennou Coil
Claymore

Summer 2007
Higurashi no Naku Koro ni Kai
Sayonara Zetsubou Sensei
Baccano
Potemayo
School Days

Fall 2007
Sword of the Stranger
Aria the OVA: Arietta
Moyashimon
Ghost Hound
Sketchbook: Full Color's
Minami-ke
Bamboo Blade
Shion no Ou
Genshiken 2
Nasu: Migratory Bird's Suitcase

This wasn't actually that great a season, but the shows were so blutig even at that second-string level that it made it hard to choose.... I had to reluctantly leave out Mokke, which really deserves to be amonst the bottom end of this list....

Winter 2008
Aria the Origination
Zoku Sayonara Zetsubou Sensei
True Tears
Spice and Wolf
Shigofumi

blutig Ariafag that I am.

Spring 2008
Kurenai
Code Geass R2
Tower of Druaga: The Aegis of Uruk
Allison to Lillia
Kaiba

Only just failed to make it: Toshokan Sensou

Summer 2008
Natsume Yuujinchou
Hidamari Sketch x365
Xam'd Lost Memories
Eve no Jikan
Mahou Tsukai ni Taisetsu na Koto: Natsu no Sora

Fall 2008
Mouryou no Hako
Ga-Rei Zero
Nodame Cantabile: Paris-hen
Hyakko
One Outs

Winter 2009
Zoku Natsume Yuujinchou
Maria-sama ga Miteru 4th Season
Kemono no Souja Erin
Birdy the Mighty Decode 2
Denpa Teki na Kanojo

Spring 2009
Eden of the East
Isekai no Seikishi Monogatari
K-ON!
Hayate no Gotoku 2
Cross Game

Summer 2009
Tokyo Magnitude 8.0
Summer Wars
Umineko no Naku Koro ni
Spice and Wolf 2
Cencoroll

Some tough choices, here.

Fall 2009
Aoi Bungaku
Kimi ni Todoke
Tatakau Shisho: The Book of Bantorra
Natsu no Arashi: Akinai-chuu
11eyes

And this last one almost made me cry. Looking back on all the other seasons, it was really only comparable to Winter 2000 in quality.... Where the 00's started.

Mappy wrote:Winter 2001
Shin Getter vs Neo Getter

Oh come on SWEET YOU EFF OH!

No love for Banner of the Stars III? Sure it's an OVA, but you've put others just as short in.
Really though, I'd agree with your comments. Except I'd replace Claymore with Koutetsushin Jeeg. That bundle of Uncle Go silliness was far more entertaining than watching characters who should not be anywhere near Clare at that point in time deciding to return for a bland climax.

Fall 2002
Haibane Renmei
Ghost in the Shell: Stand Alone Complex
Gundam Seed
Kiddy Grade
Overman King Gainer

I had completely forgotten those were all from the same period. It's kind of funny to see how some gorgeous animation came out at the same time as SEED's nightmarish digital colouring and shonky CG.

Playing necromancer on this thread. Continuing the vague ranking w.anking.

Winter 2010
Durarara!!
Nodame Cantabile Finale
Heartcatch Precure
The Legend of Koizumi
Sora no Woto
Mahou Shoujo Lyrical Nanoha the Movie 1st
Baka to Test to Shoukanjuu
Katanagatari
Hidamari Sketch xHoshimittsu
Welcome to the Space Show
Hanamaru Kindergarten
The Disappearance of Haruhi Suzumiya

Spring 2010
Tatami Galaxy
Trigun: Badlands Rumble
Working!
Rainbow
Major 6th Season
Heroman
Arakawa Under the Bridge
Ookiku Furikabutte: Natsu no Taikai-hen
House of Five Leaves
Giant Killing
K-On!!
Angel Beats

Summer 2010
Shiki
Colorful
Black Lagoon: Roberta's Blood Trail
Seikimatsu Occult Gakuin
Mitsudomoe
Sengoku Basara Ni
The Borrower Arietty
Bungaku Shoujo Memoire
Strike Witches 2
Amagami SS
Kuroshitsuji II
Loups=Garous

Fall 2010
Shinryaku! Ika Musume
Kuragehime
The World God Only Knows
Toaru Kagaku no Railgun OVA
Arakawa Under the Bridge x 2
Tamayura
Soredemo Machi wa Mawatte Iru
Toaru Majutsu no Index II
Star Driver
Bakuman
Otome Youkai Zakuro
Super Robot Taisen OG: The Inspector

Winter 2011 now is the winter of our discontent
Level E
Hourou Musuko
Baka to Test to Shoukanjuu: Matsuri
Mahou Shoujo Madoka Magica
Fractale
Gosick
Yumekui Merry
Kore wa Zombie Desuka?
Kimi ni Todoke 2nd Season
Infinite Stratos
Otona Joshi no Anime Time: Kawamo o Suberu Kaze
Mitsudomoe Zouryouchuu!

Spring 2011
Steins;Gate
Hanasaku Iroha
Fireball Charming
Gyakkyou Burai Kaiji: Hakairoku Hen
Hyouge Mono
Kizuna Ichigeki
Ano Hi Mita Hana no Namae o Bokutachi wa Mada Shiranai
Dororon Enma-kun Meramera
The World God Only Knows II
Ojii-san no Lamp
Denpa Onna to Seishun Otoko
Tiger & Bunny

Summer 2011
Mawaru Penguin Drum
Ikoku Meiro no Croisee
Natsume Yuujinchou San
Usagi Drop
No.6
Kamisama no Memo-chou
Baka to Test to Shoukanjuu Ni!
Nurarihyon no Mago: Sennen Makyou
Itsuka Tenma no Kuro Usagi
Kamisama Dolls
Dantalian no Shoka
Carnival Phantasm

I look at that list and think to myself “Just how do people think modern anime is bad?” Post 2005 each year had\has more than 5 mega hits as opposed to 2 or 3 from previous years.

kiddtic wrote:I look at that list and think to myself “Just how do people think modern anime is bad?” Post 2005 each year had\has more than 5 mega hits as opposed to 2 or 3 from previous years.

The same sort of sentiment that kept our old trams going for as long as they did. People like what was part of their generation and tend to dislike what happens to it thereafter.

Except our new trams genuinely are awful.

I also enquire upon our most endeared well-established and generously-portioned rat/mouse/weasel creature thingo whom lent its' moniker; what of the past couple seasons (say, Fall 2010 onwards) is going to appeal to an dummkopf who loved the ficken out of Hidamari Sketch and all other assorted "turn brain off" styled anime prior? I have been on something of a hiatus for the past year or so since falling over mann, der mit löchern spielt.

I find Sketchbook and G.A. cover Hidamari's territory, but they're not really within the timeframe, so....

Tamayura (the short ova.... the tv series is coming soon)
MM!
Tantei Opera Milky Holmes
Megane na Kanojo
Morita-san wa Mukuchi
Nichijou
A Channel
Softenni
Denpa Onna to Seishun Otoko
Ikoku Meiro no Croisee
Rou Kyuu Bu!
Yuru Yuri

Not all of them are good, but they roughly fit the criteria you've laid down.
Unless, of course, you want me to broaden said criteria.

"Watching a litter of kittens playing" is how I would describe it. Cute fluff you don't need to think too hard about.

I have to think all day at work, anything that makes me do it at home can ficken off.

Tamayura: Photography? Seems to blend in with the general theme of the evening.


MM!:

Themes: fanservice, Harem, moe, s & m, tsundere

Awesome.

Tantei Opera Milky Holmes: Hmm... Maybe.

Magane no Kanojo:

Plot Summary: Four short stories about girls who wear glasses.

I like how Japan can capture and concentrate concepts like these. How long before we get a set about girls who prefer the striped kind?

Morita-san wa Mukuchi: Does this show have a lot of the girls' internal dialogue? Please say yes.

Nichijou: Heard about it on /u/ of all places. It's now on my list of things to obtain motivation to download.

A Channel:

Theme: yuri

In.

Softenni: An anime about tennis. I enjoyed the one about baseball I watched. Heard about one for basketball which is supposed to be good (to people such as myself, that it). Can't see why tennis will be any less suitable. Although if they grunt every time they swing I may need to adjust the volume here. Might sound suspicious to an outsider.

Denpa Onna to Seishun Otoko: Huh. Maybe.

Ikoku Meiro no Croisee: Another maybe. Does strike me as an interesting plot line, one that could produce something of high value. But then again this is Japan we're talking about.

Rou Kyuu Bu!: Speak of the devil.

Yuru Yuri: Yuri is my anti-drug.

In any case, your services are appreciated. Got more reasons to reignite my torrent program... if I can remember where I left it.

I wouldn't put Nichijou on that list, it's more of a 'pure' comedy. The characters are neither likeable nor appealing, which would be fine if it was actually funny.

Which is a shame because it very rarely is.

Ill vouch for A Channel. Its a good show, starts off slow and cliche but picks up its own unique vibe later. The characters are all likeable and aren't annoying.