I remember fondly interacting with him quite a bit 20 years ago early (?) in his "crazy bob" phase on theserverside.com, and the epic flamewars around Java backend frameworks and app servers. Quite a shock to hear of his death.
I vividly remember being sucked into his craziness more than a few times in my formative years!
A fun, welcoming guy and an incredible technologist.
Just curious what was he like in terms of the craziness? Partying? Skydiving?
I remember arriving at a conference with serious jet lag and just wanting to sleep. I grabbed dinner with a few of the other speakers and Bob's energy was enough to turn dinner into drinks and drinks into skipping the whole night's sleep.
"Obie is one of those Ruby developers with no programming experience"
http://blog.crazybob.org/2007/09/gavin-king-on-activerecord....
A bit sad to see all those deadlinks in the comments though. From what I recall sites like JRoller were captured by the Way Back machine, but images seem to have been lost. At least they were for my blog at the time.