Fortune 500 rank: 391
2010 revenue: $5.9 billion
10-year annualized return: -14.5%
CC Media is the parent company of Clear Channel Communications, the radio station and outdoor advertising owner that was one of the best performers of the 1990s thanks to an acquisition binge. After capturing a huge share of its markets, Clear Channel began to attract private equity shops hungry for a deal.
In 2006, Bain Capital Partners and Thomas H. Lee Partners took the company private, just in time for the recession to cripple advertising revenues. Clear Channel ran into a cash crunch but survived. It now operates over 850 radio stations. (Note on the stock chart: Because the company was taken private then relisted, the stock chart does not cover the full ten year period.)
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Last updated May 05 2011: 2:52 PM ET