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.

At Warner Amex, 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.

[5] During Pittman's tenure, MTV responded to this criticism by Rick James by actively soliciting and championing videos by Black artists, including Michael Jackson and Tina Turner, and later launched Yo!

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.

[9] 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.

[11] Pittman and his team grew Century 21 Real Estate through a strategy that included brand-building and national marketing, a new franchise sales organization, and the early adoption of the Internet as a lead-generating tool.

[12] 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.

In April 2018, Pilot Group sold its stake in Casa Dragones tequila brand 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.

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.

Today Pittman is chairman and CEO of iHeartMedia, Inc., with multi-platform assets across broadcast radio; digital; podcasting; mobile; social; data; and live events.

Pittman is a philanthropist, building community and philanthropic projects into businesses he managed from Live Aid at MTV to educational efforts using the Internet at AOL.

Pittman has also served on the boards of companies including Electronic Arts, Atari Games, Excite, 3DO, MTV Networks, America Online, HFS/Cendant/Realogy and AOL Time Warner.

Pittman was one of the minority owners of the New York Mets, holding a 4% stake in the baseball team,[24] before selling his interest to Steven Cohen in 2020.