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21 — Jerry Seinfeld

Jerry Seinfeld Famous FailureBorn in 1954, in Brooklyn, New York, Jerry Seinfeld is a famous American comedian and actor best known for his role in the hit television series by his own namesake, Seinfeld, which aired from 1989 through 1998. However, it’s Seinfeld’s earliest failures that are most notable when speaking about his success in life.

In 1976, at the age of 22-years old, after graduating from Queens College, Seinfeld tried his hand at standup during an open-mic night in New York City where he froze on stage, forgetting the joke. From the second row, a heckler asked, “Is this your first time?” He was booed off the stage and felt miserable about the failure. But he didn’t stop. He simply kept going.

He continued his stint of standup acts over the next three years, which eventually led to an appear on an HBO Special for Rodney Dangerfield, and afterwards, to a role on the sitcom, Benson. In 1981, Seinfeld appeared adjacent to Johnny Carson on, The Tonight Show.

In 1988, at the age of 34-years old, Seinfeld created the semi-fictional series about his life with co-creator, Larry David and pitched it to NBC. It was originally named, The Seinfeld Chronicles, but was later changed to simply read, Seinfeld. In 2002, TV Guide ranked it as the greatest show of all time, then subsequently ranked it the second greatest show of all time in 2012.

22 — Jim Carrey

Jim Carrey Famous FailureBorn in 1962 in Ontario, Canada, Jim Carrey is a renowned comedian, actor and entrepreneur, and quite possibly one of the most famous comic minds of our time. However, his early years were distraught with a string of failures, with a childhood steeped in poverty, which didn’t help his cause or because his family was unable to help Carrey support his ambitions.

In 1977, at the age of just 15-years old, Carrey’s family ran into severe financial problems, forcing them to move to a Toronto suburb where they all worked at the Titan Wheels factory. Carrey took a job as a janitor, doing 8-hour shifts after school had let out. However, after they left their factory jobs, they lived out of a VW camper van until they could afford enough money to move back into a house.

Once Carrey’s family had financial stability, he made his standup debut at a Toronto comedy club called Yuk Yuk’s. Supported by his dad who made the drive to help aid his son to follow his dreams, he bombed during his first time on stage. However, he didn’t give up, even after the painful failure that it caused to be heckled and booed off stage, much like Jerry Seinfeld experienced initially.

Carrey kept at it. In fact, he dropped out of high school to pursue his passion. Eventually, in 1979, at the age of just 17-years old, Carrey moved to Los Angeles, and found his way into a regular standup gig at The Comedy Store on Sunset Blvd in Hollywood. However, after a failed marriage, and 5 years had passed, Carrey threw himself into acting roles. Initially, it didn’t pan out, but he kept at it.

In 1990, after 11 years of trying to pursue his dreams, he got his break to appear on a show called, In Living Color. But it wasn’t until 1994, at the age of 32, when he got his biggest break to star in the film, Ace Ventura, 15 years after arriving in Hollywood. It was that role that helped to catapult him into stardom. While he suffered through major failure along the way, Carrey’s fame is now much talked about around the world.

23 — J.K. Rowling

Famous Failures: J.K. RowlingQuite possibly one of the most famous and renowned former-failures of our time, J.K. Rowling is the author of the wildly-popular Harry Potter series of books. Born in 1965, she grew up with a tumultuous childhood that included a difficult and oftentimes-strained relationship with her father, and dealing with the illness of her mother.

In 1982, at the age of 17-years old, she attempted to gain acceptance to Oxford University. She failed and was rejected, instead enrolling at the University of Exeter where she received her Bachelor of Arts in French and Classics. After graduating from university, at the age of 21-years old, she moved to London to work for Amnesty International in 1986.

After London, she moved to Manchester with her boyfriend. It was there, in 1990, at the age of 25-years old, while on a 4-hour-delayed train, when the idea of a young wizard popped into her mind, later stating that it came “fully formed,” and all she needed to do was flesh out the details.

However, it was just a few short months after that her mother, Anne, died from Multiple Sclerosis, leaving her extremely distraught and upset. In the wake of her mother’s death, only a few months afterwards, she moved to Porto, in Portugal, to teach English. There, she met a man, got married, got pregnant, and gave birth to her daughter, who was born in 1993.

The relationship was a very strenuous one, with reports of domestic abuse, resulting in a separation and eventual divorce. With only three chapters of Harry Potter completed, at the end of 1993, when she was at the age of 38-years old, she moved to Edinburgh, to live with her sister.

At that point, she considered herself a major failure. She had failed at just about everything she had ever attempted to do in life. She was diagnosed with clinical depression and was suicidal. Two years later, in 1995, five years after the initial idea had come to her, she managed to finish the manuscript for Harry Potter and the Sorcerer’s Stone. She located an agent, but after one year of trying to get it published, all 12 major publishing houses had rejected her book.

It wasn’t until 1996, when a small literary house in London named, Bloomsbury, gave the green light and a very small advance of£1500, only due to the behest of the owner’s daughter, that the book was published. In 1997, seven years after the initial idea for the young wizard, the first Harry Potter book was published. By 2004, Rowling had become the first author to become a billionaire through book writing, according to Forbes.

24 — Jack London

Famous Failures Jack LondonBorn in 1876, Jack London is an American novelist who penned the poignant classics, The Call of the Wild and White Fang. He was put up for adoption by his biological mother who had attempted suicide at the time. She shot herself after news of the pregnancy after William Chaney, her husband at the time, demanded that she have an abortion.

At the age of 21-years old, in 1897, while in attendance at the University of California in Berkley, London wrote to his father, Chaney, who denied that he was the boy’s dad, instead sending him a letter that chastised him and his biological mother. Completely distraught by this, London quit Berkley and moved to the Klondike to live in the wilderness for a year.

Upon returning, he had committed to mastering the art of writing, deciding to write at least 1,000 words per day no matter what the situation. Realizing that mastery would come only through this method, he followed through with his goals, working from sunup until sundown, every single day without fail.

Yet, with every piece that he would mail to a newspaper or magazine, with the enthusiasm that he would get published, failure after failure returned in the envelopes that were sent back. No one was willing to publish his writing. After some time, he tired of the feeling of failure and rejection.

However, by 1899, after the rise of lower-priced technologies for printing presses that resulted in a boon for magazines, his first story had been published. In that year, he had earned a respectable $2,500 through his writing, equivalent to about $70,000 in today’s dollars when accounting for inflation.

Yet, London suffered through more than 50 separate rejections during a 5-month period of sending out his manuscripts and writing to various publishers. Just a few short years later, in 1903, at the age of 27-years old, London’s celebrated novel, The Call of the Wild had been published, and he had reached a dizzying height of success in his career.

25 — Jon Hamm

Jon Hamm Famous FailureBorn 1971, Jon Hamm is an American actor most famous for his role in the hit television series, Mad Men, which aired from 2007 through 2015. However, it’s Hamm’s early failures, and how he overcame desperation in his career to achieve success, that’s the most notable here.

Interestingly enough, after he had moved to Los Angeles, he couldn’t land a single gig. It was so bad, in fact, that his talent agency in Hollywood cut him. Distraught, Hamm began working as a waiter and had contemplated giving up entirely on the acting business, considering himself a major failure at the time.

During that period, he gave himself an objective — either he would find stable work before he reached the age of 30, or he would entirely quit the acting business. To his delight, he found work on Mel Gibson’s Vietnam War story, We Were Soldiers, deciding to then stick it out in show business.

Good  thing he did. This famous failure would eventually land the role of a lifetime in 2007’s Mad Men, turning him, not only into a famous actor, but also a cultural icon. When he was cast as Don Draper, he states that he was at “the bottom of everyone’s list.” It just goes to show you what people can accomplish when they refuse to give up on their hopes and their dreams.

26 — Katy Perry

Katy Perry Famous FailureBorn in 1984 in Santa Barbara, California, Katy Perry is an American singer and songwriter best known for her hit, I Kissed a Girl. Perry experienced a seemingly-sudden rise to fame. But did she really? In fact, Perry experienced numerous heart-wrenching failures on the path towards stardom before she ever became a household name.

In her childhood, her family faced severe struggles, oftentimes living in poverty, having to use food stamps just to get by, which had a big impact on Perry’s upbringing. From an early age, she realized that things weren’t easily obtained, and that she would have to work hard for it, something that clearly stuck with her through the failures.

Growing up, her and her siblings listened to Gospel music often. At the age of 13, she was gifted a guitar, and shortly thereafter she began performing the songs that she wrote using that very guitar. However, she was far from famous. In fact, fame was going to elude her for quite some time.

In 1999, at the age of 15-years old, she dropped out of high school after completing her GED in order to pursue music full time. She moved to Tennessee where she signed with Red Hill Records and debuted a Gospel record entitled, Katy Hudson in March, 2001 at the age of 17-years oldIt sold only 200 copies before the label ceased its operations a few months later.

In 2004, at the age of 20-years old, she signed with another label called Java, which was associated with The Island Def Jam Music Group, to work on her solo record. However, after Def Jam dropped Java, the record was shelved. Afterwards, Perry signed with Columbia Records, and recorded new music over the next two years. But before the record was completed, she was dropped from that label as well.

However, her big break came in 2007 when she signed with Capitol Records. In 2008, when she released the would-be-hit song, I Kissed a Girl, Perry was 24-years old. What seemed like an overnight success actually took 9 years to accomplish from the time that she had dropped out of high school.

27 — Keanu Reeves

Keanu Reeves Famous FailureIn 1964, the world welcomed Keanu Reeves, one of the most famous, gifted, kind-hearted and generous actors to have ever graced the Silver Screen. However, Keanu’s life was wrought with failures, most of which were completely out of his control and his hands. To say that Keanu suffered through a monumentally-difficult upbringing would be an understatement.

In fact, nothing about Keanu’s life was straightforward, nor was it common. Born in Beirut, Lebanon, where his mother, who is of English descent from Essex, met his father, an American from Hawaii, while working in the country. At the age of 3-years old, however, his father abandoned the family. Reeves kept in touch with him for the next few years, but then didn’t see him again until he was 13-years old.

His childhood was spent in multiple locations. Initially, it was in Australia, but then, he was led to Canada. His mother had married and divorced 4 times and he had been to four separate high schools in a 5-year period. When he was 17-years old, he dropped out of high school and moved to Los Angeles, obtaining a green card through his stepfather, Paul Aaron, a Hollywood director.

In 1998, Reeves married Jennifer Syme with whom he fathered a baby, who unfortunately was stillborn at eight-months old, which led to the disintegration of the couple’s relationship. Tragically, 18 months after the relationship ended, Syme died in a car accident.

Reeves starred in numerous minor roles in films prior to his breakthrough role in River’s Edge, which led to the role in the widely-popular film, Bill and Ted’s Excellent Adventure Ultimately, however, it was his role in the 1999 blockbuster movie, The Matrix, that resulted in an unprecedented rise to fame.

28 — Madonna Ciccone

Famous Failures: MadonnaBorn in 1958, Madonna Veronica Ciccone, who goes by the stage name, Madonna, is an American pop culture icon who’s often referred to as the Queen of Pop. Born in Michigan, where her father worked as an engineer in the automotive industry, Madonna lost her mother early on to breast cancer at the age of just 5-years old, which had a great impact on her life.

In 1978, while attending the University Michigan School of Music on a dance scholarship, she dropped out to move to New York City to pursue her dreams of becoming a professional dancer. With little money to support herself, she took a job at Dunkin’ Donuts. However, after an incident that occurred shortly after she was hired, where she squirted jelly on a customer accidentally, she was fired.

With only $35 in her pocket on arrival in New York City, Madonna searched for other work. She took random jobs where she could, primarily dancing as a backup dancer for modern dance troupes. One night, when she was returning home after a rehearsal, she was robbed at knife point by two men, leaving her scorned and fearful about her choices to abruptly move to New York City.

However, instead of giving up, even through all the failure and setbacks, she pushed forward. She landed small parts singing and performing with bands such as the Breakfast Club, and eventually she caught the eye of Sire Records founder, Seymour Stein. In 1982, at the age of 24-years old, she debuted her single, Everybody, followed by, Burning Up, both which became huge club hits.

Subsequently, she released her self-titled album, Madonna, and has since become one of the most famous singers to have ever lived, influencing many other modern-day singers and professional dancers.

29 — Marilyn Monroe

Marilyn Monroe Famous FailureOriginally born, Norma Jeane Mortenson, in 1926, in Los Angeles, California, Marilyn Monroe is an American actress and model who achieved extraordinary fame in Hollywood. Monroe never knew her biological father and had a sister and brother that she didn’t know about until she was 12-years old.

Monroe’s mother suffered a mental breakdown in 1934 and was diagnosed with paranoid schizophrenia. She was in and out of mental institutions for the rest of her life and Monroe had become a ward of the state, moving in and out of foster homes for the next several years, where she was sexually abused, became withdrawn and also developed a stutter.

In 1936, her mother’s family friend, Grace McKee Goddard, became her legal guardian, but she was molested by Goddard’s husband, Doc. She was in and out of homes again subsequent to that and eventually attended Van Nuys High School, but dropped out in 1942 at the age of 16-years old, marrying the son of a neighbor in order to stay in the state after the Goddard’s had to leave to West Virginia.

In 1946, after a stint of appearances on the covers of 33 magazines, she secured a contract with an acting agency, and ultimately, a 6-month contract with 20th Century Fox. During that time, she procured no work, and instead focused on taking dancing, acting and singing lessons while also spending time in the studio to observe others acting. Her contract wasn’t renewed when it came to an end, but she was determined to make things work.

However, in 1948, at the age of 22-years old, she was signed to Columbia Pictures, and starred in a low-budget movie called, Ladies of the Chorus. Still, her contract at Columbia was also not renewed. Later that same year, she signed with the William Morris Agency, with the persistent attitude to never give up.

Still, her big breakthrough didn’t come until 1950, when she had appearances in a couple of critically-acclaimed films. Since then, her films went on to gross over $200 million, and subsequently turning her into a pop culture icon and sex symbol.

30 — Mark Cuban

Mark Cuban Famous FailureBorn in 1958 in Pittsburg, Pennsylvania, Mark Cuban is an American entrepreneur and pop culture icon, owner of the Dallas Mavericks and star of the hit television show, Shark Tank. However, things weren’t always so rosy for Cuban. He learned failure the hard way, by failing numerous times, again and again before he ever attained any semblance of fame.

In his earliest years, Cuban was always a tinkerer with an entrepreneurial spirit. From selling garbage bags to running newspapers and everything in between, Cuban learned early on how the mechanics of business worked, but that didn’t mean he didn’t experience the gut-wrenching pain of failure along the way.

In 1982, at the age of 24-years old, he moved to Dallas, Texas, on the word of some of his college friends, in a 1977 Fiat X19 that had a hole in the floorboard. Upon his arrival, he worked numerous odd jobs. He simply couldn’t find something that he was good at.

He failed at bartending because he couldn’t open a bottle of wine without the cork falling in. He failed at short-order cooking because he never knew when the food was ready unless he cut off a piece and tasted it. And he failed as a salesman at a computer distributor when he was fired after less than a year on the job.

Cuban simply couldn’t get anything right. At the age of 25 years-old, one year after he arrived in Dallas, he decided to start his own company, MicroSolutions, selling software, doing training and configuring networks and computers. He grew that company to $30 million dollars in revenue, and it was later acquired by CompuServe in 1990 at the age of 32-years old.

That gave him the ability to create Broadcast.com in 1995, at the age of 37-years old, a company that was later acquired by Yahoo in 1999 when it was sold for $5.7 billion in stock. Cuban was 41-years old, famous and wealthy beyond measure. Although he had failed numerous times and been through the ringer, he never gave up.