Pirate Radio
There is probably no more interesting radio listening than pirate radio.  Pirate radio broadcasters are, in the most basic definition, stations that broadcast without a license.  Pirate stations have been found on the AM broadcast band, shortwave, and the FM broadcast band.   The reasons some radio hobbyists take to the airwaves and risk being busted by the FCC are numerous.  Probably the most common reason is that they are tired of the standard radio programming on local or shortwave stations and just can't resist putting some original programming of their own on the air.  Or it may just be the desire to be a real DJ, and not just a webcaster.  Since pirates are breaking FCC rules anyway, their broadcasts usually have an anything-goes attitude.  Programs can be anything from entertaining to monotonous and boring.  Not everyone can be like Robin Williams in Good Morning Vietnam.  But making programs without placing limits on their creativity makes most pirate operators produce some very original and entertaining programming.

Currently most North American shortwave pirates are active around 6925 KHZ nightly from around 2200-0400 UTC.  6900 is also another well-used pirate frequency, as well as the old standbys 6950 and 6955.  You may need to tune around to find them, but most will be around the area of 6900-6990.  Europirates can usually be found around 6200-6300.  Transmissions are usually either in SSB or AM, though some ham radio modes such as slow-scan TV (SSTV) have been used.  Weekends and holidays are also good times to catch shortwave pirates, especially on Halloween.

There may also be some AM or FM broadcast band pirates in your area.  FM pirates are usually only found in larger cities due to the properties of VHF radio propagation, but there may be an occasional pirate in smaller communities.  AM broadcast band pirates are more rare than FM or shortwave pirates, but they have existed in the past and may pop up from time to time. 

Pirates normally don't operate with set schedules, since it would be easier for the FCC to track them down.  When writing to a pirate station for a QSL, never ask for a schedule.  Hearing a pirate on the air can be hit-or-miss, which adds to the challenge of listening to them.  However, there is a mailing list available where pirate listeners send out email alerts of current pirate activity.  The address is [email protected].

QSL'ing shortwave pirates is another fun part of listening to them, and most shortwave pirates welcome and readily QSL correct reception reports.  If you're lucky, you may even get a studio recording of the program you listened to, a bumper sticker, or some other memento from the station.  Normally pirates require three first-class stamps to cover postage since most pirates operate with a maildrop, and the stamps are required to send the reception report from the maildrop operator to the pirate, then from the pirate to the maildrop operator, and then from the maildrop to you.  This ensures security for the pirate.  Send your reception report to whatever address the pirate announces.  Some of them will even QSL via email.  Pirate radio QSL's are as creative and diverse as the stations themselves.
Links

The Free Radio Network is probably the best pirate website on the internet.
The ACE - Association of Clandestine radio Enthusiasts site.  Pirate loggings, message boards, and various other pirate information.
Pirate Radio Central Chris Smolinski's pirate radio site, with links to many pirate sites

And, for the heck of it,
a page of FCC enforcement actions.
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