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.

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.

[60] 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.

[61] 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."

Clear Channel also entered into a deal with Providence Journal Company, who owns Fox affiliate KMSB in Tucson to operate KTTU through a local marketing agreement.

[132] These moves didn't sit well for Clear Channel Television, whose president Dan Sullivan thought they wanted to affiliate it with the ousted networks, including NBC in Mobile, and ABC in Memphis.

[140] Once FCC relaxed its duopoly rules, Clear Channel acquired stations that were originally LMA markets outright, including WLMT in Memphis, KTFO in Tulsa, WTEV in Jacksonville, KASN in Little Rock and WJTC in Mobile.

iHeartMedia owns Mediabase, which provide music charts based on songs and tracks receiving the most spins played on radio stations in the United States and Canada.

Operates urban bicycle sharing systems in several European cities: In 2003, Clear Channel created the Vertical Real Estate division and hired Scott Quitadamo to promote its tower portfolio.

iHeartMedia hip hop, rap, R&B, and rhythmic stations are branded as "Real" (KRRL Los Angeles), "Beat" (KQBT/Houston, WBTP Tampa) or "Power" (WWPR-FM New York City, WUSL Philadelphia and WHEN Syracuse).

Secondary talk stations (KEIB Los Angeles, KDFD and KHOW Denver, WKRC Cincinnati and WKJK Louisville) carry most of the syndicated offerings from Premiere Networks.

Weekend programs heard on some iHeart-owned stations and syndicated by Premiere Networks to other talk stations include At Home with Gary Sullivan, Handel on the Law with Bill Handel, The Weekend with Michael Brown, In the Garden with Ron Wilson, Rich on Tech with Rich DeMuro, The Ben Ferguson Show, Sunday Nights with Bill Cunningham, Somewhere in Time with Art Bell and The Jesus Christ Show with Neil Saavedra.

Even though they are powered at only a few hundred watts, the translators allow some listeners to hear WLAC Nashville, KOA Denver and WFLA Tampa on the FM dial.

For instance, WCKY Cincinnati, KLSD San Diego, WXKS Boston, KPOJ Portland and WINZ Miami had progressive talk formats that were switched to sports.

In the all-news radio format, iHeartMedia owns one station that airs continuous locally-anchored news around the clock, except for a few hours of talk in the evening, WBZ Boston.

iHeartMedia's Adult contemporary stations are often branded as "Lite FM" (e.g. WLTW New York and WLIT-FM Chicago) or "Sunny" (KODA Houston and KTSM-FM El Paso).

Hot adult contemporary stations are usually branded as "Mix" (WMMX Dayton), "Star" (KMYI San Diego) or "MYfm" (KBIG Los Angeles).

iHeartMedia's CHR stations share a number of common brands, including "KISS-FM" (e.g., KIIS-FM Los Angeles, WKSC-FM Chicago, WAKS Cleveland, WKFS Cincinnati, WXKS-FM Boston), "Z" (e.g., WHTZ New York, KKRZ Portland, WZFT Baltimore, KSLZ St. Louis), "Wild" (e.g., WLDI West Palm Beach, KYLD San Francisco), "Power" (WWPW Atlanta, WGEX Albany, Georgia), Channel (e.g., WKQI Detroit, KHTS-FM San Diego, WCHD Dayton-Springfield), or "Hot" (e.g., WIHT in Washington, D.C., WWHT in Syracuse, NY).

Country music stations owned by iHeartMedia often call themselves "The Bull" (WUBL Atlanta and KSD-FM St. Louis) and "Big" (WSIX-FM Nashville) as national brandings.

Starting with WQBW Milwaukee (now the sports formatted WRNW) and WBWR Columbus (now WXZX), several iHeartMedia stations have adopted a 1980s-centered classic rock approach called "The Brew".

This had been intended to provide additional revenue to the artist, venue, and promoter, as well as stifle the demand for unauthorized bootleg concert recordings made by audience members.

In June 2004, Viacom/Infinity Broadcasting Inc./One Twelve Inc. filed a $10 million lawsuit against Clear Channel for breaking of contracts and non-payment of licensing fees due to the dropping of Stern's show.

[186] A technological outgrowth of earlier, tape-based automation systems dating back to the 1960s, this method—known as voice-tracking—allows for smaller market stations to be partially or completely staffed by "cyber-jocks" who may never have visited the town from which they are broadcasting.

Clear Channel claimed no responsibility for its failure to warn residents, maintaining that the city should have used the Emergency Alert System to trigger automatic equipment in place at all U.S. radio stations.

St. Pete Pride has stated that throughout its eight-year history, Clear Channel has edited the organization's advertising material, and questioned whether the rejection of these images were because they displayed same-sex couples in affectionate poses.

Magic, the 2007 release from Bruce Springsteen which contained songs that were subtly critical of then-president George W. Bush, a Republican, and his administration, was censored from air play on Clear Channel.

[197] In 2005, Clear Channel-owned KTVX was the only local television station in Salt Lake City that refused to air a paid political message of Cindy Sheehan against the war in Iraq during a visit by President Bush.

[198] On May 8, 2014, the FCC was asked to respond to a political programming complaint made against an iHeartMedia owned broadcast licensee, Capstar TX LLC by supporters of Milwaukee mayor Tom Barrett, that year's Democratic candidate for Governor of Wisconsin.

Capstar would not offer free airtime on WISN radio (a station which only features local and national conservative talk shows) to respond to statements supporting Republican Governor Scott Walker.

The custom caller service provided by Premiere Radio assures its clients they won't hear the same actor's voice for at least two months in order to appear authentic to listeners who might otherwise catch on.