The Digital Millennium Copyright Act (DMCA) is a United States copyright law that implements two 1996 treaties of the World Intellectual Property Organization (WIPO). For our purposes, the DMCA is the rule-maker of what can and cannot be legally broadcast on Internet Radio. The DMCA is concerned with digital rights management (DRM) and it must be upheld. The DMCA criminalizes the production and distribution of technology, devices, or services intended to circumvent measures that control access to copyrighted works.
That said, Live365 has a built-in DMCA compliance checker for your Playlists and AutoDJ. The Pop-out player is also DMCA compliant. Just make sure that you don't publish your track listings in advance and be sure that you own an official copy of all the tracks that you are intending to play.
If you want to know the specifics of how the DMCA relates to Internet Radio, you can read through the following rules from the US Copyright Code:
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Sound Recording Performance Complement. A Webcaster must comply with the “sound recording performance complement,” which prohibits a Webcaster from transmitting, within any given three hour period:
(A) more than three different songs from the same album, with no more than two such songs transmitted consecutively.
(B) more than four different songs by the same artist or compilation, with no more than three such songs transmitted consecutively. -
No Prior Announcements. A Webcaster must not publish an advance program schedule that discloses: (i) the titles of specific songs, (ii) the names of albums or (iii) the names of artists to be transmitted (with exception).
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Programming Rules. A Webcaster’s programming must also comport with the following rules: (a) Archived Programming. An archived program must be at least five-hours long and cannot be made available for more than two weeks; (b) Looped Programming. A continuously looped program must be at least three hours long. (c) Rebroadcast Programming. A rebroadcast of an identifiable program that contains songs, which are played in a predetermined order (other than an archived or continuous program) and is less than one-hour in length, can be transmitted no more than three times in any two-week period when the program has been publicly announced in advance (with exception) and no more than four times in any two-week period when the program is one-hour or more in length (with exception).
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Prohibition of False Affiliation. The Webcaster must not knowingly contemporaneously play or synchronize a song to visual images in a manner that is likely to confuse as to the affiliation of the copyright owner of the Sound Recording or the artist with the Webcaster or a particular product or service.
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Cooperate to Defeat Scanning. The Webcaster must cooperate to prevent (to the extent feasible) listeners from automatically scanning the Webcaster's transmissions to select a particular song to be transmitted (with exception).
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Limit Duplication by Recipient. The Webcaster cannot affirmatively cause or encourage the duplication of songs and if the Webcaster uses technology that allows them to limit the ability to duplicate songs directly in a digital format, the Webcaster must set such technology to limit the ability to duplicate songs to the extent permitted by the technology.
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No Transmission of Bootleg Copies. The Webcaster must use Sound Recordings that are legally sold to the public or authorized for performance by the copyright owner of the Sound Recording and that are legally manufactured (with exception).
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Accommodate Technical Protection Measures. The Webcaster must accommodate and cannot interfere with the transmission of technical measures that are widely used by copyright owners of Sound Recording[s] to identify or protect copyrighted works if such measures can be transmitted without imposing substantial costs on the Webcaster or result in perceptible aural or visual degradation of the digital signal (with exception).
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Transmission of information. The Webcaster must display the title of the song, the title of the album, and the featured recording artist to the listener as the song is being played (with exception).