Jann Wenner, Founder, Rolling Stone, and chairman, Wenner Media

Magazine publishing magnate Jann Wenner once captioned his high-school yearbook picture "Greatness knows itself." Greatness might have, but Harvard didn’t; in 1964 the college rejected Wenner’s application. Perhaps it sensed, as The Nation later suggested, that Wenner only applied to Harvard to further his “social ambition.” After dropping out of Berkeley, Wenner put his greatness to work as founder of Rolling Stone, the music magazine that chronicled the counterculture of the 1960s and ’70s. Since then Wenner’s publishing ventures have included Outside, Men’s Journal, and Us Weekly magazines. Wenner has never publicly acknowledged a bruised ego over the rejection, or the fact that his sister, novelist Kate Wenner, did matriculate at Harvard, but he has often held court with the Cambridge diaspora: he once wooed William Randolph Hearst III to edit his Outside magazine, and Prozac Nation author Elizabeth Wurtzel has written for Rolling Stone. RS has long since abandoned its original San Francisco home to set up shop in New York, and become an entrenched and profitable biweekly, prompting Nirvana’s Kurt Cobain to appear on its cover in a T-shirt that declared “Corporate Magazines Still Suck.” Rejected by the Establishment, Jann Wenner went out and created a new one.

Ted Turner, Founder, Turner Broadcasting System

When Ted Turner was a boy, every step of his education was shaped by his domineering father. Edward Turner steered his son first to military school, and then, when young Ted had his sights set on the U.S. Naval Academy, lobbied hard for Harvard. But in 1957, Turner, an average student, was rejected by Harvard, thus solving that problem. He ended up at Brown, where he excelled at sailing (a childhood passion) and aspired to major in classics. But in his junior year, Turner was expelled for chronic tomfoolery and went back home to join the family billboard business, Turner Outdoor Advertising. After his father committed suicide in 1963, Turner wholly revamped the business, expanding into new markets, most notably cable television. His masterstroke was the 1980 creation of CNN, the first 24-hour news channel. Since 1999 Turner has been a member of the Board of Trustees and Corporation at Brown, his record of delinquency apparently expunged: By today’s standards, "he certainly wasn't involved in any disciplinary action that would be considered a serious infraction," according to the Vice President for Alumni Relations, Lisa Raiola. With a net worth estimated at two billion dollars, he’s a “major donor” to the university, Raiola confirms; press accounts have put Turner's donations in the eight-figures. In 2001, Turner received the Goldsmith Award for journalistic excellence from Harvard's Shorenstein Center on the Press, Politics and Public Policy. During his acceptance speech the mogul reminded his audience that he lacked not just a Harvard degree, but any college diploma. "I want you to know how unsmart I am," he said. "This isn't rocket-science work."

Tom Brokaw, Journalist

The chronicler of The Greatest Generation and one of the premier journalists of his own time, Brokaw spoke at Harvard Class Day in 1996, where he boldly confessed his own shortcomings: After being rejected from Harvard in 1958, Brokaw told graduates, he'd "wandered that cold, hard place reserved for those who have no Harvard degree." He appears to have been referring to the Midwest. The newsman subsequently left the University of Iowa—where, he once declared, he majored in "beer and coeds”—and retreated to his home-state University of South Dakota, where he earned a bachelor’s degree in political science. After sojourns reporting for local TV news in Iowa, Nebraska, and Georgia, Brokaw went to work for NBC in Los Angeles. Clearly a young man in a hurry, he became NBC’s White House correspondent, then anchor of NBC Nightly News, a position he held until his retirement in 2004. Since stepping down, Brokaw has continued to write. He is also a donor to various conservationist causes and, of course, to the University of South Dakota.

Matt Groening, Creator, The Simpsons

In a typically hilarious episode of Matt Groening's animated sitcom The Simpsons, brainy Lisa gets a zero on a test and imagines her fate as sealed: she'll never get into Harvard. There is probably some autobiographical thread in that storyline, because when Groening applied to Harvard in 1973, the college turned him down. Harvard may not have been the right place for him; Groening admits that he only applied to the college because he "always wanted to join the Lampoon." Instead, the Portland-born cartoonist later attended The Evergreen State College, in Olympia, Wash., an experimental school founded in 1967 whose Latin motto translates, roughly, to “let it all hang out.” Groening studied philosophy there and drew the ire of his classmates by lampooning hippie-dom in cartoons for the school newspaper. Groening's restless creativity lasted well beyond college, of course. In addition to The Simpsons—a feature film of which comes out this summer—Groening created the brilliant “Life In Hell” comic strip and the sci-fi cult favorite Futurama. But Groening never completely turned his back on Harvard: The Simpsons writing staff has consistently been stocked with Lampoon veterans, whom Groening warmly refers to as "Harvard-grad-brainiac-bastard-eggheads."

Art Garfunkel, Singer and songwriter

Singer-songwriter Art Garfunkel has always reveled in his anti-establishment credentials. While performing at Sanders Theatre in 2002, the 65-year-old guitarist joked that, in 1960, Harvard had rejected him. "I had to go to Columbia” instead, he said. College in Manhattan had its advantages: Garfunkel had already enjoyed local success as half of Tom & Jerry, a teen pop-duo he formed with high-school chum Paul Simon. Thinking about becoming an architect, Garfunkel commuted from his home in Queens to Morningside Heights. He earned a B.A. in art history and a master's degree in mathematics, but, in the end, architecture was not for him. Instead, Garfunkel and Simon headed off to another Columbia—the record label—where, as Simon & Garfunkel, they recorded some of the most beautiful and long-lasting music of their era. Harvard’s decision to reject Garfunkel may have been popular music’s gain, but it probably cost the university: In 2003 Garfunkel and Simon donated half a million dollars to the Mailman School of Public Health at Columbia University.

Scott McNealy, Chairman and co-founder, Sun Microsystems

Scott McNealy, the ever-quotable tech entrepreneur, once told reporters that if archrival Bill Gates had not dropped out of Harvard, Gates might have learned what a monopoly is. Unlike Gates, McNealy earned an A.B. from Harvard in economics. But McNealy, famous for preferring hockey to class, was rejected when he applied to Harvard Business School in 1976. HBS was apparently not the only place concerned about McNealy’s work ethic: Stanford’s business school said no twice before finally accepting him. It turned out to be a good move for all parties. In 1982, Stanford classmates Vinod Khosla and Andy Bechtolsheim approached McNealy with an idea they had for networking computers. By age 30, McNealy was chairman of Sun Microsystems. McNealy didn’t forget Harvard, though; one of his teaching fellows in economics, William Raduchel, became his chief information officer.

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