As defined by co-host Garfield, On the Media covers "…anything that reaches a large audience—either electronically or otherwise…. Plus, throw into that anything that covers First Amendment issues; anything that has to do with freedom of speech, privacy, is also in our portfolio." The show explores how the media are changing, and their effects on America and the world. Many stories are centered on events of the previous week and how they were covered in the news. These often consist of interviews with reporters about the dilemmas they face in covering controversial issues.

Stories regularly cover such subjects as the use of video news releases, net neutrality, digital broadcast flags, media consolidation, censorship, freedom of the press, the influence of 24-hour cable news television coverage, media oppression, and how the media are changing with technology.

The show also addresses questions about how the media is influenced or spun by politicians, corporations, and interest groups with the intent to shape public opinion. This includes an OTM feature that covers the media's use of terminologies that may engender biased points of view, and the use of hot-button issues and code words such as Michael Moore, torture, evangelical, and islamofascist.

On the Media began in 1995 on WNYC as a local call-in show, hosted by Alex Jones. In 1997 the show went national in a magazine-style format, hosted by WNYC host Brian Lehrer. During this period, this show was hampered by Lehrer being stretched thin due to commitments from his own daily show, inexperienced producers, and the lack of an editor. In late 2000, Gladstone was brought in by WNYC's director of programming to rethink and relaunch the show.

The newly formatted OTM debuted in 2001, and since then has been one of NPR's fastest growing programs, with more than 300 public radio stations broadcasting the show weekly.