"Fear of Sleep" This American Life

Though it is a little dated, this has always been my favorite episode of This American Life. The reason is because it includes feature stories that are either sad or just really interesting personal stories, and these are offset by an excerpt of Mike Birbiglia. The way the stories are structured and ordered in the show can keep listeners for a full hour.

http://www.thisamericanlife.org/radio-archives/episode/361/fear-of-sleep