50 super successful college dropouts

For many, college provides a road to success. But it's not the only road. Here's a look at dozens of tech, business, political and media stars of the 20th century and beyond who left school without undergrad degrees, but with plenty of ambition and talent to make things happen. 

First up: Oprah Winfrey.  The Apple co-founder "may ... be one of the most famous dropouts in history," per Reed College, the liberal arts school in Oregon which Steve Jobs left after just one semester. ("I ran out of money," Jobs explained in a 1991 commencement speech at the school.)  In 2017, the Facebook CEO was a commencement speaker at Harvard University. Mark Zuckerberg dropped out of the Ivy League school in 2005 to focus on his then-young but growing social media platform.  In the late 1990s, according to an Oprah magazine interview with singer-songwriter Alicia Keys, the future Grammy-winner left Columbia University after four weeks for a music deal with Columbia Records. She was all of 16 at the time.  According to the Yale Daily News, Dick Cheney dropped out of the Ivy League school twice. (Biography.com and other sources describe the departures as Cheney having "failed out.")  Joel Osteen dropped out of Oral Roberts University as a freshman in the early 1980s. The pastor went on to help build his father's Houston evangelical church, Lakewood, into the biggest megachurch in the United States, with about 43,500 weekly visitors in pre-COVID times.  Like many elite athletes, Tiger Woods left college early to pursue his sport professionally. In his case, he exited Stanford after his sophomore year. "[T]he only regret I have in life is not spending another year at Stanford," Woods said in 2016.  The future philanthropist left Harvard after the end of his sophomore year. He would return, but drop out for good after completing his junior year. Both times, Bill Gates exited school to focus on the company he co-founded in 1975: Microsoft.    Oscar-winning actor and producer Brad Pitt is the college dropout who almost wasn't. He told "Fresh Air" that he left the University of Missouri for Los Angeles just two weeks shy of graduation. "I just felt I was done," the former journalism major explained. "I was done with it. I knew where I wanted to go." Future TV talk show host and Food Network star Rachael Ray dropped out of New York's Pace University after two years, she told Vanity Fair, because her tuition was pricey — and "it was more like I was going to school for hobbies." Her next move? Taking a job at the candy counter at Macy's.  Jack Dorsey, the co-founder of Twitter and Square, dropped out of college twice. According to a New Yorker profile, Dorsey left Missouri University of Science and Technology in his junior year for a job in New York, and then exited New York University just shy of graduation for a short-lived West Coast venture. "I felt like a failure," Dorsey would recall of his mid-20s self.   Daniel Ek is the CEO and founder of Spotify. According to a Forbes profile on the streaming mogul, Ek dropped out of Sweden's Royal Institute of Technology after just eight weeks.  Ellen DeGeneres dropped out of the University of New Orleans after "less than a semester," Parade noted. "School was just not interesting to me," she told the outlet. DeGeneres went on to find her way in stand-up comedy, sitcoms, TV talk shows and Oscar-hosting duties.  In the late 1990s, Ashton Kutcher was studying biochemical engineering at the University of Iowa when he dropped out to pursue modeling. The decision ultimately put him on the path to becoming an actor and tech investor.  When the teenaged Quincy Jones left the Berklee College of Music to take a gig with jazz great Lionel Hampton, he told the school he intended to return. "[B]ut I guess down inside ... when you go with a band like that you never go back," the music legend told NPR.  By Ralph Lauren's own bio, the future designer and founder of the famous Polo brand dropped out of New York City's Baruch College after two years to enlist in the U.S. Army.   Steven Spielberg dropped out of Cal State Long Beach in the late 1960s to direct for TV. After winning three Oscars, the blockbuster filmmaker resumed his studies, and earned his bachelor's degree at Long Beach in 2002.  Kat Cole is the former president of Focus Brands, the parent company of Cinnabon, Auntie Anne's and more. She dropped out of the University of North Florida at age 20 because she was finding it difficult to juggle studies with her growing responsibilities at Hooters, the restaurant chain where she'd begun working as a teenager.  According to Hunter College, future box-office star Vin Diesel was an English major at the New York campus in the late 1980s. He left school to pursue acting.  Asked by the San Francisco Chronicle where he went to school, JetBlue Airways founder David Neeleman put it succinctly: "University of Utah. But I dropped out." Neeleman said a Mormon missionary experience in Brazil broadened his horizons; the "A" student would leave school to start his own travel business.  Now famous for flashing her smile on the red carpet, Sofia Vergara studied dentistry in college in her native Columbia. "But I didn't finish," the "Modern Family" star said in a 2016 talk-show appearance.  President William McKinley is one of only two college dropouts to serve in the 20th century White House.  The future rap and Yeezy mogul attended both the American Academy of Art and Chicago State University, but he graduated from neither. In the end, West earned a batch of Grammy Awards for his 2004 album, "The College Dropout."  Madonna called herself a "famed high-school dropout" in a 1983 "American Bandstand" interview with Dick Clark, but she's actually a college dropout: According to the University of Michigan, the pop icon studied at the Big Ten school for two years before moving to New York — and into the spotlight. In 2015, a few years after including R. Donahue Peebles on its list of the wealthiest Black Americans, Forbes pegged the real estate developer's net worth at more than $700 million. Decades earlier, Peebles dropped out of Rutgers after his freshman year to get his real estate license.  Obituaries of H. Wayne Huizenga in 2018 led with the tidbit that the man who built Blockbuster into a brand name, and owned three pro sports franchises, including the NFL's Miami Dolphins, was a once-upon-a-time dropout of Michigan's Calvin College.  Rachel Lim is a co-founder of Love, Bonito, described by CNBC as a "multimillion-dollar" fashion brand.  Harry Truman is the second college dropout to serve as U.S. president in the 20th century.  The late Paul Allen is another college dropout who went on to become a billionaire NFL owner. Allen left Washington State University after two years to take a job in Boston — where, not coincidentally, his high school computer pal Bill Gates had enrolled at Harvard. A co-founder of Microsoft, Allen owned the Seattle Seahawks from 1997 until his death in 2018.    According to Cal State Northridge, future Grammy winner and TV host Paula Abdul studied broadcast journalism and participated in cheer at the suburban Los Angeles campus from 1980-1984. Hired as a Los Angeles Lakers cheerleader as a freshman, Adbul left school, sans a degree, as her dance and choreography career heated up.   According to the University of Wisconsin-Madison, Frank Lloyd Wright "took classes part-time for two semesters" there in the late 1880s. That was the beginning and end of Wright's college career. He would go on to design New York City's Guggenheim Museum, and be hailed in his lifetime as "the greatest architect of the 20th Century." Life hasn't always been smooth for the billionaire mogul behind Beanie Babies. In court documents, it was stated that Ty Warner had to drop out of Michigan's Kalamazoo College in the early 1960s "because he could no longer afford tuition." Warner pleaded guilty to tax evasion in 2013.  On her way to becoming an acclaimed author, Jamaica Kincaid took night classes in photography at the New School for Social Research in New York City. She would go on to attend New Hampshire's Franconia College, she would say, "because I thought maybe I should go to college." But writing assignments beckoned — and Kincaid left school to nab them.  "I didn't last long there," footwear designer and fashion mogul Steve Madden once told CBS News of his college years at the University of Miami.  In 2014, Sean "Diddy" Combs was a commencement speaker at Howard University. The future Bad Boy music mogul and Sean John fashion  entrepreneur dropped out of the school in 1990 after two years of study.  Ryan Seacrest studied journalism for one year at the University of Georgia before dropping out in 1992, according to the campus news outlet, the Red & Black. Seacrest left to pursue the radio and TV gigs that would make him the media impresario he is today.   New York University's Tisch Drama includes the Grammy- and Oscar-winning Lady Gaga on its alumni list; the former Stefani Germanotta attended the school in the late 2000s, but did not stick around to graduate.  James Dean arrived at UCLA in 1950 as a pre-law transfer student from Santa Monica College. In short order, the future "Rebel Without a Cause" icon changed his major to drama, won his first stage role in a campus production of "Macbeth," got a bad review — and dropped out to try his luck on the New York stage.  Like James Dean a year before him, Paul Newman dropped out of college — in Newman's case, Yale — to head to New York. Newman and Dean would both become famous for their movies and for helping popularize the methods of method acting.    The daughter of Broadway star John Raitt, Bonnie Raitt was an African studies major at Harvard's Radcliffe College when she fell in with the blues music scene that would take her to Philadelphia (her first break from college) and a 1970 tour with the Rolling Stones (her second break).   When Travis Kalanick dropped out of UCLA, his disappointed parents held their tongue because, as his dad once explained to the HuffPost, they "knew something was going to work out for [him]." And it did. In 2009, Kalanick co-founded the ride-hailing giant Uber.   "If you don't know, I should confess," tech mogul Michael Dell said in an address at the University of Texas at Austin's 2019 spring commencement. "I dropped out of UT after two semesters." Dell was in a hurry to devote himself to his namesake computing business.  According to an early Newsday profile of the comic actor in 1981, Eddie Murphy attended New York's Nassau Community College for two weeks. Not long after, he would drop into "Saturday Night Live," and, at age 19, become a breakout star.  R. Buckminster Fuller, the innovative architect and engineer who gave the world the geodesic dome, is a two-time college dropout via expulsion. In 1914, per Fuller's official biography by the Buckminster Fuller Institute, the future great was dismissed from Harvard "after excessively socializing and missing his midterm exams." Upon a return to campus in 1915, Fuller was expelled again.  CNN founder and former Atlanta Braves MLB owner Ted Turner is another who left college via expulsion. According to a New Yorker profile, Turner was kicked out of Brown University "for smuggling a coed into his room." Within a few years, Turner's father would commit suicide and the 24-year-old would inherit and exponentially grow the family's advertising company.  In the 1970s, future professional poker champ Johnny Chan studied hotel and restaurant management at the University of Houston. But he dropped out at age 21. Dustin Moskovitz dropped out of Harvard along with roommate Mark Zuckerberg to work on Facebook. The co-founder of the social media giant told Startups.com that it wasn't their intent to "permanently" leave the campus.  David Geffen dropped out of the University of Texas at Austin after less than a year, according to a PBS timeline of the agent turned media mogul. Geffen went on to co-found DreamWorks with Jeffrey Katzenberg and fellow college dropout Steven Spielberg.  According to Apple co-founder Steve Wozniak, he "never dropped out" out of the University of California, Berkeley — he "simply took a year off to earn money for [his] fourth year of school," and didn't return for more than a decade.  Micky Arison dropped out of the University of Miami to help his father, Ted Arison, run the one-ship operation that originally was Carnival Cruise Lines. He would become a regular on lists of the world's wealthiest people, and hoist three NBA Finals trophies as owner of the Miami Heat.  In 1975, the future media mogul and philanthropist left Tennessee State University for a TV job one credit shy of completing her four-year degree. A decade later, after launching her talk show and earning an Oscar nomination, Winfrey resumed her studies. She graduated as a member of Tennessee State's Class of 1986.  The future U.S. vice president would eventually settle into higher education and earn bachelor's and master's degrees at the University of Wyoming.  "I pursued something I was passionate about and … I haven't felt like I've worked a day even though I work every day," Kutcher told Newsweek of leaving college. "So, that was the right decision for me." Cole is a different kind of dropout on this list because while she never earned a bachelor's degree, she does hold an MBA. She pursued the graduate degree after becoming a Hooters vice president in her mid-20s.   According to Pennsvlvania's Allegheny College, which McKinley attended, it's not known why the future U.S. president didn't complete his degree. The school says McKinley called his lack of a diploma "one of the greatest regrets of his life."  "I was kind of bored with school," Peebles told C-Suite Quarterly. "I wanted to be busier."   Lim was months away from graduating from Nanyang Technological University in her native Singapore when she bet on her then-fledgling business.  Sources generally list Truman's higher-education resume as consisting of a semester at an unnamed Kansas City, Missouri, business school, and night classes at what was then known as Kansas City Law School. He didn't earn a degree at either campus.  Madden dropped out after his father stopped paying the tuition and ordered the disinterested student to get a job.  "I'm going to take a leave of absence," the future Grammy winner told Radcliffe, she later related to Oprah.com, "but this is only going to last a year." Spoiler alert: It didn't. "I just couldn't work 9 to 5," Chan told New Times. "The action always gets me. The action makes me who I am." "[But] it would be impossible to run the company while we were also going to school," Moskovitz said. "I don't know how we thought that was ever going to work." True to his word, if not timeline, Wozniak earned his bachelor's of science degree from Berkeley in 1986.