One rainy, miserable day a few months ago I was at home, sick, and I stumbled upon an episode from the web series “Wainy Days” by David Wain. I felt better for laughing so much. I then proceeded to watch all episodes back to back, like a laughter junkie.
The web series follows a fictionalized version of Wain through his everyday life as he tries to form relationships with numerous women and discusses his problems with his friends at the sweatshop where he works.
At present there are two entire series online. Above is the last episode of the second series. You can watch all episodes on MyDamnChannel.

A promising new web series, completely different to Wainy Days, is Take Me Back.
I saw the first two episodes today, and it looks like it could be a fun series. The site (where you can watch all currently released episodes) is pretty nice too.