For most of the 90's he was somewhat muted. An irrelevant relic really. But professional wrestling and a tv game show let him resurrect his spot in the public eye. He then found that the more he made controversial statements the more attention he got so he just kept saying crazier and crazier things.
And don't forget about his cameo in Home Alone 2.
I was watching it last Christmas and it really took me out of the film for a second to reflect on the fact that trump was soon going to be my president.