Clear Channel Communications is one of the companies taking a serious look at the assets of Playlist.com, the once promising digital music service that filed for bankruptcy protection last summer, according to a source with knowledge of the negotiations.

Details are few, but apparently Clear Channel, the media conglomerate with a large stake in broadcast radio, concert promotion, and billboard advertising, is interested in the user interface and other technology belonging to the defunct Playlist.com, once known as Project Playlist.

Playlist.com, which enabled users to create and share music playlists with friends, filed for bankruptcy protection in August, and at the time company leaders suggested Playlist.com might manage to reorganize and re-emerge. Records show that there was little hope of that.

In the company's Chapter 11 filing on August 6, it reported $2.2 million in total assets (only $203,000 in cash). Playlist.com owes the four largest record companies a combined $25 million.

It's still not clear what Clear Channel would want to do with Playlist.com's assets. A Clear Channel representative said "the company doesn't comment on rumor or speculation." One of the attorneys overseeing the bankruptcy also declined to comment.

After thumbing its nose at the music industry by operating without obtaining music licenses from most of the labels, Playlist.com had to spend big on legal fees.

To critics of the big labels, Playlist.com was crushed by big licensing fees. Music industry insiders, on the other hand, say Playlist.com was a classic example of a start-up that built a large following by offering free music and worried about licenses later.