Grantham has called 15 of the last 3 market crashes. when the next one happens he will be able to say he called it. 

I've listened to numerous podcasts featuring Grantham over the years. It's always the same thing. Very bearish on everything except the VC investing he is doing. Eventually, he will be right.

Hussman is super smart and I enjoy reading his posts. He is always bearish but provides heaps of interesting data to back up his thoughts.

https://www.hussmanfunds.com/comment/mc210715/

I like the following quote I heard somewhere: "the pessimist is eventually right but the optimist is rich"