The Melancholy of Haurhi Suzumiya-Kyoani Anime, first aired in 2006
Miss Kobiyashi's Dagon Maid-Cute Kyoani show from 2017. Worth noting this is a yuri.
Lucky Star-Another Kyoani one, from 2007.
Fate-Huge franchise, not sure exactly what iteration the image is from, but the original is 2006
B-gata H Kei-Plot of this one is a teenager who wants to have sex with 100 guys before graduating. I've heard she doesn't actually get anywhere, but still, shit loose girl Digi.
Code Geass-Popular enough to air on Adult Swim, show is from 2006
Gunsmith Cats-Action manga from the early 90s
Bleach-One of the big three Jump manga aired in 2002 and ran on Adult Swim.
K-On!-His favorite show right? Aired in 2009. The girl he has on here is a lesbian.
Darling in the FranXX-Waifu of the season in 2018
Nadia secret of the Blue Water-Cult classic from 1990
Panty and Stocking with Garterbelt-Trigger raunchy comedy from 2010
Caanan-Action show from 2009
Puella Magi Madoka Magica-Shaft's magical girl money-maker. Worth noting this show has a lesbian vibes despite not being a yuri. 2011.
Sayonara Zetsubou Sensei-The best anime ever made, from 2007
Katanagatari-Anime aired in 2010
Yokohama Kaidashi Kiko- Classic manga, an OVA came out in the late 90s
Kabanari of the Iron Fortress-Fun action show from 2016, Digi defended this one a lot when it first came out.
Redline-2009 theatrical movie
Oran High School Host Club-Shojo from 2006. The girl here is a reverse trap.
Lyrical Girl Nanoha-Magical girl show from 2004. I think this is a yuri.
Arakawa under the Bridge-2010 Shaft comedy.
New Game!- Cute girl show, from 2016
Princess Tutu-Ballerina themed magical girl show. Kinda dark. 2002
The Wind Rises-Ghibli film from 2013, this character is fictional in case you were wondering.
School Live!-2015, cute girl zombie show.
Hidamari Sketch-Cute girl show, has major yuri vibes. 2007.
Haibane Renmei-Neat slow paced angel anime. 2002
FLCL-Very popular aired on Adult Swim. 2000
Urusei Yatsura-Popular 80s series
Sword Art Online-The series he inspired the hatedom of. 2012
Kanokon- Ecchi from 2009
Kill la Kill-Fun fanservice show, very popular from 2013
.Hack-The character in particular he picked is from Sign the 2002 series
Bakuon-Motorcycle cute girl show. Surprised he likes it, not bad, but generic. 2016
Revolutionary Girl Utena-Classic shojo with yuri vibes. 1997