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  StationRipper - get songs from 100's of radio stations
Years ago, I tried a media player call WinAmp and I found a plugin for it called StreamRipper. Using StreamRipper I could tune into an internet radio station and record over 100 songs a night. I'd go through them the next day and keep the ones I liked. Now with StationRipper the inteface for recording the songs has been made a bit easier to use. I haven't used the "chat" option in StationRipper but it sounds pretty cool. Naturally, the songs you take can only be for personal use and should never be offered on a file sharing network.
Website - Quote from the website (some of the features here are not available on the free version)
Record Shoutcast Audio and Video streams.
Records up to 300 streams at one time.
Buy the music you are ripping
Keeps track of the songs you've already recorded, only keeping the songs you don't already have.
Lets you easily find stations to record, via the StationRipperTM Portal, Shoutcast, or other web sites.  Or you can drag and drop from iTunes radio to start recording.
Keeps a list of the music and stations you've recorded, allowing easy playback and re-recording of stations.
Listen to any station being recorded with a single mouse click.
Ignore songs under a certain size.
Auto-record whatever was being recorded the last time you ran StationRipperTM.
Chat with other users, sharing what stations you are listening to.
Clif Notes Freeware and Website Reviews