Darker and Edgier/Web Animation

"Singer: There's new demographics when nobody asked for it!"
 * The There She Is series of videos at http://www.sambakza.net/ feature Doki and Nabi, a rabbit who falls in love with a cat. The first two videos are cute and funny, showing Doki chasing Nabi despite his arguing that they are different species, then him getting her a birthday cake. The third and fourth videos show how society is REALLY against this pairing, with the two of them getting injured, property destroyed, pet dying, etc. Not so fun anymore, huh?
 * JibJab, originally, light in tone, went from gently mocking Bush and Kerry in 2004 to mocking McCain and Obama straight up in 2008, along with the broken promises made by presidents in election day that never come to light when they are actually in office. The "Year in Reviews" went from hoping it'll get better to, most recently, the 2008 Year in Review summing up everything that's bad, and even adding "wars and famine" to the end.
 * Super Smash, the gritty reimagining of Super Mario Bros makes itself to be a rather awesome flash.
 * Homestar Runner parodies this with its 2010 April Fools' Day gag, HSR Xeriouxly Forxe.


 * The third season of Gotham Girls is much darker and realistic than the last 2. In fact, many DCAU fans consider this to be the ONLY canon season.