Did you know Fountains Of Wayne released a new CD last year? No? Well, it was crap... except for one song called "I Hate To See You Like This." If you liked them back in the day, or maybe even if you didn't, you'll want to check it out. It's at the end of this playlist.
A long time ago, I wrote a How-To for creating an iTunes Jukebox. Each time I post a playlist here, I dump the songs into an iTunes playlist called jTunes. It's sort of my own 'best of' playlist that's handy for filtering my mega-massive 25,500+ song iTunes library when I want a random list of favorites. And then, when I REALLY want to filter the list to all time favorites, I add an iTunes rule that says "only play songs in my jTunes playlist rated 4 stars or higher."
iTunes is easily the very best music software for generating playlists - especially smart playlists based on rules. Want to hear songs from the 90s that you've rated at least 4 stars? iTunes can easily do that.