10 Underdogs We Can’t Help But Love

Close-up of a chessboard where a white pawn faces a black king.

Whether it has to do with sports, Hollywood, or a casino games table, everyone loves a good underdog story. The unexpected wins, seemingly impossible trials, and victory against all odds are heart-warming and triumphant moments for us all. Stories of unknown men and women who braved the stakes and became heroes, unexpected sports stars working hard to beat the odds, and those whose relentless commitment to their vision saw them becoming legends after much rejection, demonstrate the power of the human heart and inspire us towards greatness. 

Read on as we explore 10 compelling stories of the underdogs we simply can’t help but love! 

Muhammad Ali

When it was announced that 22-year-old Cassius Clay (as he was known at the time) would go head-to-head with heavyweight champion Sonny Liston in 1964, even with an Olympic gold medal already under his belt, no one thought the young fighter stood a chance. Liston was the most feared heavyweight of the time, who would destroy any and all competition. 

However, Clay beat Liston in only six rounds, and in their second fight a year later, Liston didn’t even last a single round against Muhammad Ali, aka “The Greatest,” who had by then changed his name.

Jim Carrey

Jim Carrey grew up in Toronto, Canada in a struggling family who were not strangers to sleeping in a VW van or in tents. He dropped out of school at age 16 and worked as a janitor in a factory. His first debut at a comedy club was a flop, and he failed a Saturday Night Live audition in 1980. However, Carrey was steadfast and kept at it, eventually building a name for himself through open-mic performances at local comedy clubs. 

As his popularity spread, Carrey eventually landed some significant roles including Ace Ventura: Pet Detective, Dumb and Dumber, and the outstanding movie, The Truman Show. That’s right: A once homeless kid from Toronto worked hard and went on to become one of our most-loved comedy stars of all time!

Ben Keeline

Ben Keeline was an Uber driver who could barely afford the entrance fee to the World Series of Poker Colossus II tournament in 2016. He borrowed money from his father and made his way, along with 22,000 other players, to the tourney and gave it his all. The path was not easy, and he thought about throwing in the cards many times during the initial stages. 

At one point, Keeline was forced to go all in when he had only one bet’s worth of chips left, but with an unparalleled string of double-ups, he managed to move forward in the tournament. In fact, he saw himself right through to the end: He went home champion with $1,000,000 in poker winnings, making himself the underdog all online casino table games fans were rooting on!

JK Rowling

JK Rowling onstage at the RFK Ripple of Hope Awards in New York, December 2019. (Photo by Dia Dipasupil/Getty Images)

JK Rowling was once a divorced mother living on welfare with clinical depression. In 1995, having finished Harry Potter and the Philosopher’s Stone, she was rejected by a dozen publishing houses.

Well, a few years later, it’s safe to say that her novels are some of the most famous ever, as is her name. Rowling has sold more than 400 million copies and the Harry Potter books are the best-selling series in history, having also spawned an entire franchise of movies, games and even theme parks!

Jim Morris

Baseball pitcher Jim Morris was drafted by the Yankees in 1982 and spent eight years in the minors, never advancing to the majors. He then retired and went on to teach and coach at a high school for a decade. 

In 1999, Morris made a deal with his high-school team that if they won district, he would try out one last time for a major league team. The team did indeed win and so Morris tried out for the Tampa Bay Devil Rays (as it was then known) at age 35. Clocking 98 miles an hour on the pitch, Morris was signed into the MLB and pitched for two years before retiring, having finally fulfilled his dream.

Louis Armstrong

Louis Amstrong was born in New Orleans in 1901. His mother had him at the age of 16 and his father abandoned the family soon after. Armstrong was raised in a poverty-stricken neighborhood locally known as “The Battlefield,” and was sent to a juvenile facility at the age of 11. 

Despite his difficult upbringing, Armstrong developed a strong connection with music and went on to become one of the best jazz musicians to have ever lived.

Colonel Sanders

Colonel Harland Sanders, founder of Kentucky Fried Chicken. (Photo by John Olson/Getty Images)

Every chicken lover’s favorite white-haired grandpa, Colonel Sanders (born Harland Sanders), was a seventh-grade dropout who, after having lied about his age to enter the army, tried everything from selling tires to operating ferry boats! Eventually, he opened a small restaurant in Kentucky, before setting off to travel the country (often sleeping in his car,) and spread the news of his secret recipe for the world’s best fried chicken. 

At the age of 62, Sanders sold his first “Kentucky Fried Chicken” franchise, and in 1964 at 73 years old, he sold the company for $2 million. We wonder if he could ever have imagined just how popular his fried chicken is today. We salute you, Colonel Sanders!

Golden State Warriors

In 2007, the Golden State Warriors finally made the NBA playoffs for the first time in 13 years. At the time, the Dallas Mavericks were the West’s No.1 seed, with the sixth-best mark in the league’s history. Channeling their slogan, “We believe,” San Francisco’s Warriors managed to beat the favored Mavericks, and became the first No.8 seed to defeat a No.1 seed in a best-of-seven series. However, the Warriors didn’t even need seven games – they won the series 4 games to 2!

Susan Boyle

Susan Boyle was raised in a coal-mining town in Scotland and lived with Asperger syndrome, which went undiagnosed for many years. When she first stood on stage at the age of 47 for her first audition at Britain’s Got Talent, she looked entirely out of place in front of the TV cameras and the audience. The judges were clearly unimpressed, having seemingly already made up their minds about her. When asked what her intention was, Boyle said, “To become a professional singer,” which many in the audience scoffed at. When asked why she’d not made it yet, she replied, “Because I haven’t been given a chance” – an experience many of us can relate to. 

However, when Boyle started singing “I dreamed a dream” from Les Misérables, she shocked the world with her incredible voice, and brought the audience (and two of the judges) to a standing ovation. Boyle has since gone on to fulfill her dreams with an incredibly successful singing career, and has sold nearly 20 million copies worldwide. (It’s well worth finding her audition on YouTube if you’ve never seen it before!)

Warren Moon

In 1978, Warren Moon, though being named the Rose Bowl game MVP, went undrafted because the NFL apparently didn’t believe an African-American could play at the highest level. Moon was thus forced to go to the Canadian Football League for five years, where he won the Grey Cup every year.

At the age of 28, Moon landed in the NFL, and managed to establish himself as one of the greatest quarterbacks of all time. He remains the only player ever to have been inducted into the Canadian Football Hall of Fame and the Pro Football Hall of Fame.

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