My theory is that at some point around 1999, someone kidnapped the Chris Matthews who used to rail against Bill Clinton night after night and talk about how disgusted he was with how Bill and Hillary were dealing with the Lewinsky scandal, and replaced him with a dogmatic, liberal robot. But perhaps now the old “blue collar Democrat” Matthews escaped and got back on the air somehow.
In the mid 90s, he filled in for Rush Limbaugh.