I never thought about this before. I was 11 when Bloom County started and 26 when Calvin and Hobbes ended. I consider myself very fortunate to have had the opportunity to read both as they were published.
I don't think either have been matched since. Not for a guy growing up anyway. I don't want to take anything away from Trudeau and others. But for me that was an amazing thing that my youth and those strips lined up so perfectly.