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.