Podcaster and Comics Journalist Chris Sims is also obsessed with Funky Winkerbean and after having Josh from joshreads.com on his podcast War Rocket Ajax he started writing a monthly recap of all the things that happen to characters in the Funky Winkerbean Universe for Comics Alliance. This is the wrap up of the most depressing Funky Winkerbeans and Crankshafts for the month of October: http://www.comicsalliance.com/2012/11/01/funkywatch-octobers-most-depres...
As someone who still reads some of the print comics Funky Winkerbean and Crankshaft still shock me with how depressing and horrible they can be.

If you want an example of exactly what I'm talking about scroll to the end of this article from January 2011: http://www.comicsalliance.com/2011/02/02/funkywatch-januarys-10-most-dep...
It's from the January 1 2011 Funky Winkerbean. In it Les(who is the character who had a wife die from cancer) is seen standing kissing a a beautiful woman as other people cheer "Happy New Year". In the second panel you see the two women who are at that point fighting over his affection enter the room to see him kissing the air as he is spending New Years Eve thinking about how much he misses his dead wife.
Again: Rather than spending time with EITHER OF THE TWO WOMEN WHO WANT TO MARRY HIM he is standing by HIMSELF, thinking of his dead wife. If these were real people I wouldn't want to mock it, but this is a DAILY COMIC STRIP.