Year is less than "1986"
Year is greater than "1900"
Genre is not "Holiday"...
Comment contains "radio"
This is yet another smart playlist that requires some work on your part (and some mental exercise!) as you have to add "radio" to your comment tags on all songs that were part of radio rotation "back in the day". Obviously, change the "Year less than" to the year after you graduated from high school, college, or any point in your life and it's like you're listening to your favorite radio station when you were younger!
I'd like to perfect this by adding more weight to the songs that actually fall in the "Year is less than" year, but I don't think there's a way to do that.