A high-flying media mogul—he was one of the founders of MTV and later served as the No. 3 at AOL Time Warner—he's currently the CEO of Clear Channel Communications.
The son of a Mississippi Methodist minister, Pittman didn't get off to a very auspicious start: More interested in rock 'n' roll than studying, he attended four colleges but didn't graduate from a single one. Not that it mattered. Having arrived in New York in 1977 to work at the radio station WNBC, in the early '80s he landed at Warner-Amex, where he found himself in charge of a new concept the company was toying with—a cable network that would play nothing but music videos. The idea, of course, was MTV, which launched in August 1981. Pittman went on to help revamp Nickelodeon and was part of the team that created VH1 and Nick at Nite. When the company was purchased by Viacom for more than $500 million in 1985, Pittman was named MTV's CEO. Two years later, Pittman left MTV after an unsuccessful attempt to buy out the network, and he spent a decade in a variety of other top corporate jobs. (He launched Quantum Media, ran Time Warner's Six Flags amusement parks, and served as CEO of the real estate company Century 21.)
In 1996, Pittman joined Steve Case at AOL after Case hired him as the company's president. One of the chief proponents of the 2001 merger between AOL and Time Warner, Pittman was the man responsible for selling the deal to Wall Street and following the merger, he became the No. 3 executive at the combined company. When it became abundantly clear that the deal had been a major strategic misstep and Time Warner shareholders mounted a revolt following the collapse of the dot-com boom, Pittman (along with bosses Steve Case and Jerry Levin) were shown to the door. The AOL-Time Warner fallout proved to be a rare career misstep for Pittman. But he didn't skulk off and fade away, nor did he exactly walk off empty-handed. He started investing in the web with The Pilot Group, which he sold in 2010. Pragmatic as ever, Pittman has since become the CEO of Clear Channel.
Pittman's first wife was 1980s social fixture Sandy Pittman, whom he married in 1979. Part of the city's swirling social scene and "a prime example of New York's astonishing display of late-80's wealth," Sandy is probably best remembered for climbing Mount Everest in 1996 with her espresso maker in tow, a trip that left eight people dead. Bob and Sandy's divorce was finalized in 1997; later that year he married divorcee Veronique Choa, a web designer and graphics artist. [Image via Getty]