iHeartMedia

Clear Channel Communications purchased its first FM station in San Antonio in 1972. The company purchased the second "clear channel" AM station WOAI in 1975. In 1976, the company purchased its first stations outside of San Antonio. KXXO and KMOD-FM in Tulsa were acquired under the name "San Antonio Broadcasting" . Stations were also added in Port Arthur, Texas and El Paso, Texas from John Walton Jr. In 1992, the U.S. Congress relaxed radio ownership rules slightly, allowing the company to acquire more than 2 stations per market. By 1995, Clear Channel owned 43 radio stations and 16 television stations. When the Telecommunications Act of 1996 became law, the act deregulated media ownership, allowing a company to own more stations than previously allowed. Clear Channel went on a subsequent buying spree, purchasing more than 70 other media companies and individual stations.In a few cases, following purchase of a competitor, Clear Channel was forced to divest some of its stations, as it was above the legal thresholds in some cities. In 2005, the courts ruled that Clear Channel must also divest itself of some "border blaster" radio stations in international border cities, such as the alternative rock radio station XETRA-FM in Tijuana, Baja California/San Diego.

In 1997 Clear Channel moved out of pure broadcasting when it purchased billboard firm Eller Media, which was led by Karl Eller.

In 1998 it made its first move outside of the United States when it acquired the leading UK outdoor advertising company More Group plc, which was led by Roger Parry; Clear Channel went on to buy many other outdoor advertising, radio broadcasting, and live events companies around the world, which were then re-branded Clear Channel International. These included a 51% stake in Clear Media Ltd. in China.In 1999, the company acquired Jacor Communications, a radio corporation based in Cincinnati. The company also made an investment in the new satellite radio service XM Satellite Radio, giving it the rights to program a selection of stations on the service .R. Steven Hicks and Hicks, Muse, Tate & Furst began Capstar Broadcasting in 1996, and a year later had become the largest owner of radio stations in the country, with 243 stations in total. In August 1997, Capstar and Hicks, Muse, Tate & Furst announced plans to acquire SFX Broadcasting, with the resulting company owning 314 stations in 79 markets and ranking as the third-largest radio group by income. A year later, Chancellor Media Corporation and Capstar Broadcasting Corporation announced a merger that would result in Chancellor Media owning 463 stations in 105 markets when the deal was completed in second quarter 1999. Hicks, Muse, Tate & Furst owned 59 percent of Capstar, with 355 stations in 83 markets, and was the largest single owner of Chancellor , with 15 percent of the stock. Chancellor Media later became AMFM Inc., which was acquired by Clear Channel in a deal announced October 3, 1999, and valued at $17.4 billion. The resulting company would own 830 radio stations, 19 television stations, and over 425,000 outdoor displays in 32 countries.In 2000, Clear Channel acquired Robert F. X. Sillerman's SFX Entertainment, a concert promoter that had focused on consolidation of regional promoters under a national operation. In 2005, Clear Channel spun off its entertainment and live events business as Live Nation.

Leveraged buyout

On November 16, 2006, Clear Channel announced plans to go private, being bought out by two private-equity firms, Thomas H. Lee Partners and Bain Capital Partners for $26.7 billion, which included their assumption of $8 billion in Clear Channel debt. This was just under a 10 percent premium above its closing price of $35.36 a share on November 16 . In a separate transaction also announced on November 16, 2006, Clear Channel said it would seek buyers for all of its television stations and 539 of its smaller radio stations, because the private-equity buyers were not interested in owning television or small-market radio. Over a hundred stations were assigned to Aloha Station Trust, LLC upon the consummation of the merger. The television stations were sold to Newport Television, a broadcaster owned by Providence Equity Partners, on April 23, 2007.Due to the credit market crunch of 2007, Clear Channel had difficulty selling some of its radio stations. Clear Channel's attempt to sell off over 100 stations to GoodRadio.TV, LLC was rejected by the equity firm backing the deal. The deal then shifted to Frequency License LLC, but took longer to resolve itself as the two parties were engaged in lawsuits. On top of that, the sale of Clear Channel's television portfolio to Newport Television had also turned uncertain, as Providence considered other options, although this transaction was ultimately completed.On December 4, 2007, Clear Channel announced that they had extended the termination date of the buyout from December 12, 2007, to June 12, 2008. On July 24, 2008, Clear Channel held a special shareholder meeting, during which the majority of shareholders accepted a revised $36-per-share offer from Bain Capital and Thomas H. Lee Partners. Shareholders received either $36 in cash, or one share of CC Media Class A common stock for each share of Clear Channel common stock held. The company announced that it would move to more centralized programming and lay off 1,500 employees, or approximately 7% of its workforce, on January 20, 2009. The reasoning was bleak economic conditions and debt from its transition to a private company. By the completion of the restructuring in May 2009, a total of 2,440 positions were eliminated.

iHeartMedia, bankruptcy

In early 2010, it was announced that the company was facing the possibility of bankruptcy due to its "crippling debt". After 21 years, Mark Mays stepped down as president and CEO of Clear Channel on June 23, 2010. Mays remained as chairman of the board. On October 2, 2011, Robert W. "Bob" Pittman, who was then the company's Chairman of Media and Entertainment Platforms, was named CEO of CC Media Holdings.In August 2013, Clear Channel sold its minority stake in Sirius XM for $135.5 million. This also resulted in the removal of most Clear Channel-programmed stations on the service, besides simulcasts of WHTZ and KIIS-FM.On January 6, 2014, Clear Channel announced a marketing partnership with Robert F. X. Sillerman's SFX Entertainment , to collaborate on electronic dance music content for its digital and terrestrial radio outlets, including a Beatport top 20 countdown show. The partnership expanded upon the company's existing EDM-oriented outlets . Staff, including John Sykes, believed that the deal would help provide a higher level of national exposure to current and up and coming EDM artists.In September 2014, it was announced that the company would be renamed from Clear Channel Communications to iHeartMedia, alluding to its iHeartRadio platform to reflect the company's growing emphasis on digital media and internet radio. The previous name "Clear Channel" came from AM broadcasting, referring to a channel on which only one station transmits. In the U.S., clear-channel stations have exclusive rights to their frequencies throughout most of the continent at night, when AM signals travel far due to skywave. CEO Bob Pittman explained that the company had been "doing progressive stuff", yet they were still "named after AM radio stations".In 2016, one of the company's directors, Julia B. Donnelly, left the board of iHeartCommunications and was replaced by Laura A. Grattan, a director at Thomas H. Lee. Grattan was named to the board of managers of iHeartMedia Capital I, LLC, the direct parent of iHeartCommunications, as well as the board of directors of iHeartMedia, Inc., the indirect parent of iHeartCommunications.Since 2008, iHeartMedia had struggled to pay down more than $20 billion in debt the company assumed from its leveraged buyout. Various media outlets, including Bloomberg News, Reuters, Radio Ink, and iHeartMedia's hometown newspaper the San Antonio Express-News, claimed that either bankruptcy or a major restructuring was likely. On April 20, 2017, the company warned investors that it might not survive over the following 10 months. On November 30, 2017, it was reported that a group of creditors had rejected iHeartMedia's latest debt restructuring proposal, instead bringing out a deal where the company might file for bankruptcy. On March 15, 2018, the company filed for Chapter 11 bankruptcy, and claimed that it reached an agreement to restructure $10 billion of its over $20 billion in debt.

Emergence from bankruptcy, realignments towards digital

In September 2018, iHeartMedia acquired HowStuffWorks' podcast network Stuff Media for $55 million. On November 19, 2018, iHeartMedia announced its intent to acquire Jelli, the provider of a programmatic advertising platform for radio stations.In January 2019, the U.S. Bankruptcy Court for the Southern District of Texas approved a creditor-supported plan for iHeartMedia to exit bankruptcy, which would reduce the company's debt from $16.1 billion to $5.75 billion. The plan included the spin-out of iHeartMedia's 89.1% stake in its out-of-home advertising division Clear Channel Outdoor. In April 2019, the company also filed a proposed initial public offering.iHeartMedia emerged from Chapter 11 bankruptcy in May 2019, with a new board of directors and the spin-out of Clear Channel Outdoor, but maintaining its existing leadership of CEO Bob Pittman and president Rich Bressler. Rather than pursue its IPO , iHeartMedia instead received approval for a direct listing on the Nasdaq.On January 14, 2020, iHeartMedia announced a major restructuring, as part of an effort to "modernize our company to take advantage of the significant investments we have made in new technology and aligning our operating structure to match the technology-powered businesses we are now in." This included the restructuring of its Markets Group into three divisions and adding a "multi-market partnerships" unit, and the announced development of "centers of excellence" that would use its technology investments to "provide a better experience for listeners and business partners and a more efficient process for all of its employees". The restructuring was accompanied by a major round of layoffs and displacements, with a large number of staff members and on-air personalities being affected.