I love this thread! Many of my favorites have been mentioned. My first first few are acquired tastes, but I have come to really enjoy them.
- Last Podcast on the Left - true crime, aliens, paranormal, horror comedy show
- Timesuck with Dan Cummins - similar to LPotL, but single host
- Knowledge Fight - commentary on Alex Jones and others with humor
- Internet Today - opinion based comedy news for all things tech, gaming, etc.
On the shorter side:
- Everything Everywhere Daily - something new every day on various subjects
- Today in History with the Retrospectors - short daily episodes bringing you curious moments from this day in history
- Atlas Obscura - curious and wondrous travel destinations
And a classic that I don't think has been mentioned:
- Stuff You Should Know - interesting discussion about a wide variety of topics
I have added Chilluminati to try based on this thread.