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Pittman has also been a radio and TV programmer, marketer, investor and media entrepreneur who has had multiple careers in a number of consumer-focused industries. According to Sean Parker, Pittman is the only media mogul who’s genuinely an entrepreneur. In giving him its first 'Media Visionary" award, advertising publication Adweek referred to him as a "jack of all media" and former MTV executive Tom Freston referred to him as "the wonder boy of branding."

In conjunction with this position, Pittman also maintains his role as Founding Member of Pilot Group and continues his activities as a venture investor; in an indication of his continued interest in emerging technologies and businesses, he also serves on the board of live social video company Airtime. With his return to radio, Huffington Post’s media business expert Charles Warner dubbed him “best radio programmer ever” and in 2011 he was ranked by Radio Ink magazine as the "Most Powerful Man in Radio." "Never before has anyone taken the number one slot on the list in their inaugural year," stated Radio Ink Publisher/CEO B. Eric Rhoads. Pittman retained that designation in 2012, 2013, 2014, 2015, 2016, 2017, 2018 and 2019, and was also named Radio Ink's 2019 Radio Executive of the Year.

Pittman's many honors include: Robert F. Kennedy Memorial’s 2000 “Ripple of Hope Award” for his commitment to civic and community affairs and his contributions to the advancement of education; receiving the Broadcasters Foundation of America's 2016 'Golden Mike Award'; induction into the Advertising Hall of Fame and the Broadcasting and Cable Hall of Fame; received AdWeek's first Media Visionary award in 2013 and Cablevision Magazine's "20/20 Vision" award for the 20 people who have had the greatest impact on the cable industry; selection as one of Advertising Age's "10 Marketers Who Changed American Culture” and "50 Pioneers and Visionaries of TV" and recognition as one of Business Week magazine's Top 25 Executives of 1998. He was also named one of Life Magazine's "Five Original Thinkers of the '80s"; recognized as the eighth of Life Magazine's "50 Most Influential Boomers"; included in Time Magazine's 1984 Man-of-the-Year issue "Seven Others who Succeeded"; received the "Star of Hope Award” in January 2014 from the Community Foundation of Northwest Mississippi; was named Success Magazine’s “Pioneer of the New American Start-Up” in 1989; received the 1986 White House Conference on Small Business Award for Entrepreneurial Excellence and the 1984 Council of Fashion Designers of America award; Performance Magazine’s 1982 “Innovator of the Year” award for his work developing MTV and Billboard Magazine’s “Radio Program Manager of the Year” in 1977. In October 2012, he was awarded the Henry A. Grunwald Award for Public Service by Lighthouse International. He also received the American Academy of Achievement’s Golden Plate award; International Teleproduction Society’s Lifetime Achievement International Monitor Award and The President's Award and an Honorary Doctorate from Bank Street College of Education, the school's highest honor, for his many contributions to the advancement of education.

On May 4th, 2019, Pittman announced his podcast "Math & Magic: Stories from the Frontiers of Marketing." The show is produced by iHeartRadio.

Pittman was the CEO of MTV Networks and the cofounder and programmer who led the team that created MTV. Pittman joined the predecessor company Clear Channel in November 2010 as an investor and the company’s Chairman of Media and Entertainment Platforms, was named CEO in 2011 and Chairman in 2013. Clear Channel became iHeartMedia, Inc. in September 2014 to reflect its new multiplatform business. Pittman has also been the former Chairman and CEO of Clear Channel Outdoor, CEO of AOL Networks, Six Flags Theme Parks, Quantum Media, Century 21 Real Estate and Time Warner Enterprises, and COO of America Online, Inc. and AOL Time Warner.

At MTV, he oversaw the creation and growth of MTV and the transition of Nickelodeon from a failing network geared to preschoolers to the highest rated channel aimed at older kids as well as overseeing the launches of VH-1 and Nick at Nite, and led the initial public offering for MTV Networks and its expansion into international markets. Under Pittman's leadership, MTV became the first profitable cable network; then-Time Warner Co-Chairman and Co-Chief Executive Officer Steve Ross also noted that MTV became the most profitable basic cable network during Pittman's tenure there. During his tenure at MTV, the network was criticized harshly for its initial reluctance to play videos from African American artists.. For his development of the MTV brand, Advertising Age selected Pittman in 2010 as one of the ten most influential marketers who transformed American Culture.

In November 2010, Pittman took on the role of Chairman of Media and Entertainment Platforms for Clear Channel, and made a personal equity investment in the Company. In this role, Pittman worked to leverage the Company's media assets and spearhead the further development of a digital strategy for Clear Channel Radio, particularly with regard to its iHeartRadio digital radio platform. At this time, the company was burdened with $20 billion in debt as the result of a 2008 leveraged buyout. In September 2014, the company transformed to iHeartMedia, Inc. to better reflect the company's multi-platform focus. Today Pittman is Chairman and CEO of iHeartMedia, Inc., with multi-platform assets across broadcast radio; digital; podcasting; mobile; social; outdoor; data; and live events. Under Pittman's leadership the company's debt was significantly reduced -- from $16.1 billion to $5.75 billion -- and the company emerged from restructuring in May 2019. At that time, T. Rowe Price referenced the company as one that had been revived by disruptive change. iHeartMedia, Inc. is now the No. 1 commercial podcast publisher globally, and in October 2018 closed its acquisition of podcasting pioneer Stuff Media, LLC, the leading for-profit publisher of entertaining and informative podcast content, which includes the HowStuffWorks (HSW) brand and content. Pittman played a pivotal role in developing the iHeartRadio Music Festival, the biggest live concert festival in radio history, the first of which took place in Las Vegas on September 23–24, 2011 in conjunction with the launch of the New iHeartRadio. The company has since expanded its national tentpole live events platform to include the nationally televised iHeartRadio Music Awards; the iHeartRadio Country Festival; iHeartRadio Fiesta Latina; the iHeartRadio Summer Pool Party; and the iHeartRadio Jingle Ball Tour. In December 2016, the company launched its two new on demand subscription platforms, iHeartRadio Plus and iHeartRadio All Access.

Pittman joined a number of his longtime operating team colleagues when he co-founded Pilot Group LLC, a private investment firm based New York in 2003. Pilot Group previously owned and sold investments including Thrillist, which is now part of Group Nine and in which Pilot Group is still a minority investor; DailyCandy, sold to Comcast Ventures for a reported $125 million; IdealBite, which was sold to the Walt Disney Company; and entertainment research company OTX (sold to Ipsos America). Pilot also owned and sold significant minority investments in David's Bridal and Nutrisystem, and owned and sold the Barrington Broadcasting television group to Sinclair Broadcast Group in 2013 for $370 million and its radio station group Double O Radio to a variety of regional radio station groups including Town Square Media. Pilot and Pittman have also held various minority positions in digital content and technology venture companies including social gaming company Zynga, in which Pilot was an early investor; Huffington Post and Facebook. In April 2018, Pilot Group sold its stake in Casa Dragones Tequila to BDT Capital Partners LLC — Warren Buffett's banker -- which is taking the lead investor role and providing capital to take Casa Dragones to the next level -- although Pittman, as the co-founder, maintained his personal stake and remains on the board.

While at Century 21, Pittman met Steve Case and joined the board of directors of America Online, Inc.; he joined the company as President and CEO of AOL Networks in 1996 and later became President and COO of America Online Inc. While at AOL, Pittman led the operating team that moved AOL from 6 million members to over 30 million; took the company profitable; and continued the mission of making the Internet as easy for consumers to use as the telephone or television. During Pittman's tenure, AOL had almost 50% of all Internet traffic in the U.S. and pioneered the development of digital advertising. The company’s most memorable ad of that time had the tagline “America Online: So easy to use, no wonder it’s number one”. After AOL merged with Time Warner in 2001, Pittman became the Co-COO (and eventually COO) of the combined AOL Time Warner before leaving the company in 2002.

After Pittman led a process that led to Time Warner selling a controlling interest in Six Flags to Boston Ventures in 1995, he left to join Century 21 Real Estate as CEO. Pittman and his team grew Century 21 Real Estate through a strategy which included brand-building and national marketing, a new franchise sales organization, and the early adoption of the Internet as a lead-generating tool.

After MTV, Pittman founded Quantum Media with MCA (one of the company's ventures was the Morton Downey Jr. show, an early television shock talk show), and in 1989, he bought out MCA, sold the assets to Warner Communications and became senior advisor to Warner Communications CEO Steve Ross just as Warner was merging with Time Inc. to create Time Warner. In 1990, Pittman was appointed President and CEO of Time Warner Enterprises, the new business group of Time Warner, and in 1991 became Chairman and CEO of Six Flags Theme Parks where his team oversaw the revitalization of the Six Flags brand, taking attendance from 17 million to 25 million using a “classic second-place strategy” with their “Bigger than Disneyland, closer to home” positioning of the brand.

Pittman married Sandy Hill, a merchandise editor at Mademoiselle, in July 1979; they divorced in 1997. They have one son. Pittman married Veronique Choa in 1997. They have two children.

Son of a Methodist minister, Pittman was born in Jackson, Mississippi, but raised in Hattiesburg and Brookhaven where he attended Brookhaven High School and became a radio announcer at the age of 15 to earn money for flying lessons. He was an announcer in a number of cities and then successfully programmed radio stations in Pittsburgh, Chicago (WMAQ AM 670 and WKQX FM) and finally at the NBC flagship station, WNBC (AM), in New York when he was 23 years old. He also produced and co-hosted a music video and news show in 1978 that ran on NBC's O&O Television stations. He did learn to fly and has been a pilot for almost 40 years: He now has over 6,000 flight hours; currently holds an Airline Transport Pilot's license for airplanes; and is rated for helicopters and 3 types of jets.

Robert Warren Pittman (born December 28, 1953), is an American businessman.