When it comes to Western music, very few people have influenced Americans as much as Roy Rogers. Known as the “King of the Cowboys”, he performed in numerous films during the ’40s and ’50s, and played country music throughout much of the ’30s. He was one of the brightest gems of America and is still revered today. We take a look at the life of an icon through these vintage photos.
Roy Rogers had a very humble start to his life. Originally named Leonard Slye, he was born to Andrew “Andy” Slye and Mattie Slye née Womack on November 5, 1911, in Cincinnati, Ohio.
The family lived in a small tenement building on the second street – the very same place where Riverfront stadium would be built later. However, soon after Rogers’ birth, the family decided to make some changes in their lives which set Rogers’ journey in motion as well.
Up the Ohio River
Soon after Rogers’ birth, the Slye family decided to seek out their fortune in greener pastures, away from the city life. In 1912, Andrew Slye and his brother Will built a 12 by 50 ft houseboat out of salvaged lumber and decided to sail their way up the Ohio River to Portsmouth, Ohio.
The family purchased a plot of land in Portsmouth where they intended to build a house, but the Great Flood of 1913 forced them to live in the houseboat for a few more years. This is where Roy Rogers spent the earlier part of his childhood.
Love for Horses
A few years after moving to Portsmouth, the Slye family relocated again in 1919, this time to Duck Run, a farm outside Lucasville, Ohio. Roy’s father, Andrew Slye took a job in a shoe factory in Portsmouth, only coming home on weekends and bringing gifts along.
One of the notable gifts was a horse, on which Roy Rogers learned the basics of horsemanship. He had always possessed a love for horses, and this gift from his father was what set him up to be a true western star.
Born to Perform
Roy Rogers’ rise to fame was no accident. Although it came much later in life, he was already popular in his neighborhood due to his extraordinary talents. Since the location of the farm was in a rural area, the sources of entertainment were limited – with no radio to listen to.
The Slye family would often invite neighbors for square dances, during which Rogers would sing, play the mandolin and call the dances. He also learned to yodel during this time. These early performances helped him discover his passion for entertainment, which he soon followed.
High School Days
Roy Rogers, who was still Len Slye back then, attended high school in McDermott, Ohio. He was a bright kid, but he would never graduate. After his second year in high school ended, the family moved back to Cincinnati again in 1927, where his father worked in another shoe factory.
He realized that his family needed financial help, so he joined his father at the factory in Cincinnati. He tried to balance work and studies by attending night school, but he kept falling asleep, and soon called it quits on his education.
Beginning of a Legend
The Slye family relocated a few times more, and in 1931, they lived in Inglewood, California. This is where Rogers would get his first chance to shine. Rogers appeared on a radio show called Midnight Frolic. His singing and yodeling caught the interest of a local music group called “The Rocky Mountaineers”.
The group toured around several states, playing in local bars and radio shows. They eventually changed their name to “The O-Bar-O Cowboys”. The group was only moderately successful, but it planted the seeds for Rogers to become an entertainer.
Rogers began dating Lucile Ascolese in 1932, whom he met during the acquisition of a palomino colt named Golden Cloud, which Rogers renamed as Trigger. Ascolese was an admirer of Rogers, and they tied the knot in 1933.
However, their honeymoon phase was short-lived. The couple soon realized they weren’t right for each other, and felt that they rushed into a commitment too soon. Their relationship turned sour fast, and Rogers and Ascolese split up in 1936.
Although his first marriage failed terribly, love soon blossomed in Rogers’ life again. During his tour with The O-Bar-O Cowboys, Roy met Grace Arline Wilkins in 1933 in Roswell, New Mexico, where she called in and promised to bake him a pie if he sang “The Swiss Yodel”.
Rogers followed through, and the two kept in touch. After his marriage with Ascolese ended, Rogers and Wilkins began dating – and eventually married in June 1936.
The O-Bar-O Cowboys
Roy Rogers hoped to make his big break with the O-Bar-O Cowboys but it failed poorly. Many musical artists struggle in the first steps of their careers, and it was no different for Rogers. He went on tour with the Cowboys across several states, and they were fairly popular locally and in radio stations.
However, the timing was ill-fated. The Great Recession soon hit hard, and people did not have enough to pay for concerts, thus ending their tour in complete failure.
Sons of the Pioneers
Rogers’ success with The O-Bar-O Cowboys didn’t see much light, and the musical group split up by 1933. Rogers looked to form a new group, and he teamed up with Bob Nolan and Tim Spencer to form The Pioneers Trio. The Pioneers Trio was later joined by Hugh Farr, a fiddle player who added a bass voice.
Whilst performing for a radio show, an announcer changed their name to “Sons of the Pioneers”, stating they were too young to be pioneers themselves. The group graciously accepted the renaming and went along with it.
Roy’s rise to success began with music – whilst working with the Sons of the Pioneers. Since their rechristening by the radio announcer, their popularity grew widely. By the summer of 1934, their popularity extended beyond the Los Angeles area.
In the same year, they also signed a recording contract with Decca Label. The Sons of the Pioneers paved the way for Roy to get into films. The Sons had a few parts in movies as background character roles, but Roy made himself stand out and eventually found himself landing a few minor gigs in Hollywood.
Entry to Film
Rogers began to take his career as an entertainer seriously, and from 1935, he began to take baby steps into the film industry. He would often appear in supporting roles at the beginning of his career.
He made his big break in 1938 when he auditioned for a “singing cowboy” star for Republic Pictures. Rogers got the part, and he made his starring debut in 1938 in the film Under Western Stars. The film was very popular and paved his way into Hollywood.
The Split of the Sons of the Pioneers
Rogers found his first big musical success through the Sons of the Pioneers, where he worked with musicians like Bob Nolan, Tim Spencer, and Hugh Farr – with whom he would remain friends for life. However, due to contract complications, he eventually had to leave the group.
The group was contractually obligated with Columbia Pictures to appear in a few films. Thus, in order to seriously pursue his film career, he had to leave the Sons of the Pioneers to sign up with Republic Pictures.
Roy Rogers married Grace Wilkins in 1936, and they were extremely happy together. However, tragedy struck when they began trying for a baby. Doctors informed them that due to medical reasons, they would not be able to conceive naturally.
The couple was demoralized, but this did not stop them from attempting to have a family. Roy and Grace adopted Cheryl Darlene Rogers in 1941 – their first and newest addition to the family.
Surprises and Heartbreaks
Whilst doctors informed them otherwise, Roy and Grace were overjoyed to realize that they were wrong about the couple’s inability to get pregnant. Grace was pregnant soon after the adoption of their first daughter, and in 1943, they welcomed Linda Lou Rogers into the world.
In 1945, Grace was pregnant once again. She gave birth to their first son, Roy Jr. in 1946. However, it came with heartbreak for Roy as well. Grace passed away a few days later due to complications, leaving Roy Rogers devastated and widowed.
Grace’s loss was a big blow to Rogers emotionally, having spent more than a decade together. He was still determined to raise his three children by himself, but he didn’t need to. Soon after Grace’s passing, Roy reconnected with the charming actress Dale Evans.
Roy had met Evans earlier on the set of a film in 1944. After Grace passed away, the two found themselves with feelings for one another, and they married each other in 1947. The two remained married until he passed away in 1998.
Roy Rogers and Dale Evans met on set in 1944, and fell in love after his second wife, Grace Arlene passed away in 1946. They wed each other in 1947 – but it was undoubtedly a tumultuous event, which was a cause for laughs a few years afterward. The wedding was held in a ranch in Davis, Oklahoma.
The minister was delayed because of a snowstorm and had to ride up there on horseback. A fire also started in one of the upstairs bedrooms – which Roy and his best man put out, but it left Dale confused and wondering where her groom was for several minutes at the altar.
Since his first great gig in 1938, Rogers soon made a name for himself. He was arguably the biggest advocate of the Western genre with his unique charisma and natural talent for music.
He worked in popular movies like King of the Cowboys and Son of Paleface. He retained the position of the number one actor in Westerns for over a decade, a legacy that would eventually be taken over by legends like John Wayne and John Ford.
A Man of Business
Roy Rogers was not only talented in the field of entertainment, but in the field of commerce as well. He knew what he was worth. So in 1940, he wrote into his contract that he would preserve the rights to his name, likeness, and voice.
This had some serious implications. He gained tons of money from the merchandising of his identity and characters. There were Roy Rogers toys, comics, and action figures – all of whose profits were kept by Rogers.
Rogers’ first contract was with Republic Studios, which offered him the lead position of Under Western Stars in 1938. Whilst his film career with Republic was very successful, he wanted to move into television, a move that was vetoed by the studio.
Later, Rogers discovered that Republic were trying to make TV shows out of his films during the peak of popularity. Rogers owned the rights to his name and was able to stop them. He was dropped from the contract by Republic, which worked out for the best, as it gave birth to The Roy Rogers Show.
Emergence in Television
Having achieved insurmountable success in radio and film, Rogers challenged the field of television next. He ventured into The Roy Rogers Show – a western television series that portrayed Rogers as a cattle rancher who brought justice to the city.
He represented a western version of Batman, if you will. The show ran from 1951 to 1957, and still maintains an astonishing rating of 7.2 on IMDB. The show also featured his wife Dale Evans, along with his horse Trigger, and was appreciated by viewers around the US.
The Flipside of the Coin
Rogers’ career was not all highs, though. Just like a mountain has its ups and downs, so did Rogers’ time in television. Five years after The Roy Rogers Show ended, Rogers and Evans began to film The Roy Rogers and Dale Evans Show in 1962.
This show, however, did not see the light of success. It was canceled before the first season, and foreshadowed the demise of Rogers’ and Evans’ stardom – no longer being the center of the Hollywood western genre the way they once were.
Rogers’ love for horses was well known in Hollywood, and his favorite was Trigger – the palomino colt he had acquired in California. Trigger accompanied him in several films and competed with him in terms of popularity. Trigger learned over 150 tricks and even outshined Rogers in some performances.
They worked together in several films, including Rainbow Over Texas and Song of Nevada. Trigger even got his own musical film called My Pal Trigger.
Hall of Fame
Rogers was a popular figure both in the musical and the film scene, and it was only natural that he received recognition for it. He was one of the most popular figures in country music at that time.
Rogers was inducted into the Country Music Hall of Fame twice – the only person to accomplish that. His first induction came as a member of Sons of the Pioneers, and the second as Roy Rogers himself.
Walk of Fame
The Country Music Hall of Fame was not enough for Rogers; he pushed boundaries in Hollywood as well. He’d been recognized by the Hollywood Walk of Fame – and so, he received three stars to his name for his work in radio, film, and television.
Later in life, he received several other awards and accolades. In 1983, he was awarded the Golden Boot award. This followed him in 1996 when he received the Golden Boot Founders’ Award as well.
Being a celebrity has its quirks, and even more so during the ’40s and ’50s. As one of the top western actors of his time, Rogers had a very dedicated fan base. Rogers handled his fame graciously.
He would constantly receive letters from fans who would praise him, ask for his autograph, or even ask to meet him. He once received over 78,000 fan letters in a month. There were even reports of fan clubs dedicated to his horse, Trigger!
Roy Rogers and Dale Evans were immensely popular in their lifetimes, and they even had a whole museum for it. The Roy Rogers-Dale Evans museum was set up in 1967 and included a collection of memorabilia that were presented by Roy himself.
The Roy Rogers-Dale Evans museum was set up in Branson, Missouri, and included several artifacts from the couples’ careers. The museum eventually closed down in 2009 due to decreasing visitor rates.
Roy’s entry to a film career, however, was not easy. Hollywood back then put a lot of emphasis on looks, and many big stars were turned down at first because studios were not happy with their appearance.
Rogers was no different. In 1937, he appeared for a screen test for Universal Film Studios. The studio turned him down because apparently, he looked too young. Rogers got the last laugh though, turning out to be one of the biggest stars on the planet.
Becoming Roy Rogers
As we’ve mentioned earlier, Rogers was born as Leonard Slye. So how did he become Roy Rogers? And why did he choose the name Roy Rogers, in particular?
In Hollywood, studios often change the screen names of actors to get the right feel. Leonard Slye began acting with the pseudonym, Dick Weston. In 1938, when he first signed a deal with Republic Studios, they bestowed the name “Roy Rogers” upon him – as a tribute to the recently deceased Will Rogers.
Charity and Public Appearances
Roy Rogers knew he was popular, but he never let it get to his head. Instead, he used his popularity to achieve other means – such as giving back to the public in the form of charity and appearances.
One of his favorite things to do was visit sick children in hospitals, as Rogers was the most popular amongst the younger demographics. He would even take Trigger with him sometimes, who could climb stairs and navigate hospital floors.
Hollywood celebrities get a lot of spotlight from their fans, which is why many celebrities eventually turn to politics after they retire. For example, Ronald Reagan served as the President of the United States.
Rogers was asked to make a bid for the House of Representatives, but he was adamant in his position. He maintained a neutral stance in politics, citing that he had fans across the political spectrum and didn’t want to upset any of them.
The Muppet Show
Running from 1976 to 1981, The Muppet Show created by Jim Henson was one of the greatest shows to ever hit the television. The show was star-studded with guest appearances, and Roy Rogers and Dale Evans were also invited.
In an episode in 1979, Rogers and Evans appeared as a couple on the show – the only one besides Robert Shield and Lorene Jansson, and Kris Kristofferson and Rita Coolidge. The episode premiered on May 17, 1979.
What comes to your mind when you think of westerns? Desert rodeos, train robberies, a hero in a cowboy hat, and of course, a sidekick! Movies back then always included a sidekick with the hero, and Rogers was joined by one as well.
His sidekicks were often the same faces. He often co-acted with veteran sidekick actors such as Smiley Burnette, George Hayes, and Pat Brady, who were acclaimed by the audience as well.
Food for Thought
As we’ve already established, Rogers was a very intelligent and capable businessman – creating a merchandising franchise of his own name. But he was not only limited to toys and action figures. He founded restaurants as well.
In 1968, Rogers agreed to give the Marriott Company a license to establish a series of restaurants by his name. The Roy Rogers Restaurants popped up throughout the Mid-Atlantic and the North-East. As of 2019, there are still 48 locations of Roy Rogers Restaurants in the US.
Trigger was not the only horse that was loved by Rogers. He had been a fan of horses since his childhood, and he had a penchant for raising them as well. He was particularly fond of a racehorse he owned, who was called Triggairo.
Triggairo was moderately successful in his field, just like his owner. Triggairo won 13 races in the race tracks, including the El Encino Stakes in 1975, a prestigious annual race run held in Arcadia, California.
Love for Creation
Roy Rogers did not settle for acting in TV shows and movies alone, although he was certainly earning a lot of dough from it. He eventually decided to take matters into his own hand so that he could create his own projects the way he wanted to.
He set up his own production company “Roy Rogers Productions” – the same company that made The Roy Rogers Show. The company also produced Brave Eagle, the first television show with a Native American as the lead character.
To the Skies
Roy didn’t stop at horses alone. Indeed while people see him and his horse-riding intertwined immensely in his character, Roy Rogers was a fan of other modes of transportations as well. He wanted to soar high and had a passion for flying aircraft.
With his wealth, he bought a World War II-era plane- the Cessna AT-17 Bobcat. This plane wasn’t just for show though, as he also earned a pilot’s license along with it.
Roy Rogers was a family man and his wife Dale Evans shared the notion. While they already had a family owing to having children from their previous marriages, their boundless love did not stop there. They wanted more siblings for their children.
Despite being struck with the news that they would be unable to conceive any children, they did not give up. They saw adoption as a suitable option and hence the other four children named Dodie, Debbie, Mimi, and Sandy came to be a part of a larger than life family.
Sorrows Under the Smile
Pictures of Roy were always characterized by his immensely charming and cheerful smile. It is the same smile that made people unaware of the tough and dark times he had to go through.
As popular and inspiring as he was an icon of the Western genre, there was a lot of sadness and sorrow in his life that tends to take many people by surprise. His first marriage fell apart and he lost his second wife to childbirth. Unfortunately, his sorrows continued with his children.
Losing your own child is an indescribable sadness and both Rogers and Evans felt that when their biological daughter, Robin, who passed away right in front of their eyes because of heart failure.
Their world had been shattered and the news of them being unable to conceive children made it even more painful. Despite this tragedy, Rogers and Evans awoke with a newfound compassion and undying love for children and life.
While adopting is seen as a viable option in this day and age, back then it was met with disdain. However, it did not bother Roy in the slightest. Five of his nine children were adopted and they were all loved and cared for greatly and equally.
One of his adopted kids came from a previous marriage – Cheryl Darlene Rogers. After losing Robin, their biological daughter, the couple adopted four more children: Mimi, Dodie, Sandy, and Debbie.
Like Father, Like Daughter
Roger had lost three of his nine children. The oldest daughter, Cheryl Darlene Rogers grew up to be quite similar to her father. She lives an adventurous and romantic life with a similar love for western film and music as well as traveling.
She had fallen in love and later married her high school friend Larry Barnett. The two live happily together roaming the countryside in their trailer alongside their seven children. Truly like father, like daughter.
Influential and Inspirational
Considering how much of an influence Roy Rogers was in the film and music industry then, it is not much of a surprise to see how much he had inspired his own kids to pursue the arts.
Acting and performing were natural to them and no other better example is there except for Mimi Rogers. She grew up to be an iconic American actor with recurring roles in popular TV shows such as Mad Men, The X-Files, and Bosch. She was also the first wife of Tom Cruise, another charismatic actor much like Roy himself.
While Roy Rogers is often seen as the epitome of charisma and confidence his path to Hollywood wasn’t so easy at first. He was faced with difficulty and failure due to his shy nature and struggled to perform in many shows including his own radio show.
Yet Roy’s attempts to overcome his shyness and triumph over it make his story both relatable as well as inspirational. He believed that he could do it and never gave up.
Turning Sadness Into Strength
The Rogers and Evans couple had to go through several hardships in their personal life. They lost Robin to Down syndrome, and another daughter passed away due to mumps before her second birthday.
Knowing what it is like to deal with Down syndrome, the parents realized the importance of raising awareness about the condition. Dale Evans later wrote a book called Angel Unaware, which highlighted the care that she and Rogers gave to the baby.
Rogers and Evans were immensely successful in their careers, and were the hottest couple in Hollywood for quite a while. They knew this could affect their kids, and cause them to grow up spoiled.
Luckily, Rogers and Evans were role models as parents. They raised their kids on a ranch – away from stardom and surrounded by nature. They wanted to keep their children away from Hollywood, but even then, their son Dusty acted in two movies even before leaving high school.
Between 1935 and 1951, Roy Rogers was a name in every American household. Everyone had heard of him – either through movies, radio, or television. During that time, he appeared in at least two films a year.
However, once his family began to grow, he started to take things a bit more slowly. Whilst sometimes he still acted in as many as eight films in a year, he began to concentrate more on his family and slowly deviated from the glamor of Hollywood.
Not only is Roy Rogers popular, but his residences are popular as well. His place of birth – the original home of the Slye family – was a tenement building in Cincinnati.
The building was later demolished to make room for the Riverfront Stadium, one of the most popular stadiums in America, responsible for being the host to several Cincinnati sports teams, including the Cincinnati Bengals of the NFL and the Cincinnati Reds of MLB. Rogers later joked that he was born on second base.
The California Ranches
In 1955, Rogers and Evans purchased a 168-acre ranch near Chatsworth, California along with a hilltop ranch house. After their daughter Debbie was killed in a bus accident in 1964, they moved away to the Double B Bar Ranch in Apple Valley, California where he and Evans raised their children.
The Double B Bar Ranch which was estimated to be worth $3.7 million in 2019, when it was looking for a buyer.
Roy Rogers passed away on July 6, 1998, in his home in Apple Valley, California. He was 86 years old, with his wife Dale Evans and other family members at his side.
Besides his frail age, he had also undergone numerous heart surgeries in his later years, which contributed to his death. Known as “King of the Cowboys”, he may have left the world, but still resides in our hearts – beloved for his extraordinary performances, superb musical skills, and firm personality.
The Richest Songwriters of All Time and Their Net Worth
Songwriting can be a lucrative field, especially if your music is featured in a successful advertising campaign or film. Some songwriters choose to write music for other artists, whilst others want to hold onto the glory and sing their own tunes. Keep reading to find out about the richest songwriters of all time.
Ariana Grande – $50 million
Ariana Grande originally found fame on Broadway before moving onto television. After a few other gigs, Grande decided to pursue a career in music. To this day, all five of her albums have been certified platinum.
Paul Simon – $55 million
As part of folk duo Simon and Garfunkel, Paul Simon’s music has captured hearts across the globe. He was responsible for writing some of their most famous hits, including “The Sound of Silence,” and “Bridge Over Troubled Water.”
When they decided to call it a day in 1970, Simon continued to write hits, releasing a host of albums under his own name. His timeless solo efforts such as “Me and Julio Down by the Schoolyard” have earned him 16 Grammys!
Michael Bublé – $60 million
Every Christmas, homes and shopping malls across the world are filled with the dulcet tones of Michael Bublé, thanks to his chart-topping festive albums. However, his own music is also highly successful, and he has sold millions of records worldwide thanks to his soulful voice and catchy, swing-inspired pop songs.
In 2018, there were rumors that he was set to retire from the music industry, but thankfully, his manager denied these claims. He shows no signs of stopping just yet!
Bruno Mars – $150 million
Before he was famous, Bruno Mars (born Peter Gene Hernandez) lived a humble life in Hawaii. In 2003, he decided to pursue music and moved to Los Angeles, where he hustled, gigged, and honed his songwriting craft.
It was a fruitful move, and he was signed to Atlantic Records in 2009. Some of his most famous hits include “Grenade,” “Lazy Song,” and “Finesse.” He has also written a host of hits for other artists including Adele, B.O.B, and The Vamps.
Janet Jackson – $275 million
While she may not have made as much money as her most famous sibling, Janet Jackson is still one of the richest songwriters of all time. The youngest Jackson’s first taste of stardom came in 1976 when she performed on their family variety show, The Jacksons.
Her big break came in 1991, when she signed a multi-million dollar recording contract with Virgin Records. Thanks to her powerful stage presence, memorable songs, and dancing ability, she has become a pop icon.
Tim Rice – $200 million
If you’re a musical theater nerd, then you know all about Tim Rice. He’s most famous for being Andrew Lloyd Webber’s right-hand man, co-writing some of the most successful stage shows of all time, such as Joseph and the Amazing Technicolor Dreamcoat.
He has also worked with Swedish megastars ABBA and written songs for Disney’s Aladdin and The Lion King. In 1992, he was given a knighthood by Queen Elizabeth II for his contribution to the music industry.
Calvin Harris – $220 million
Born Adam Richard Wiles, Calvin Harris began his career recording music in his bedroom in Dumfries, Scotland. He was discovered by record label execs on early social media platform MySpace, and since the release of his debut album I Created Disco in 2007, he has become an international success.
He has topped Forbes‘ list of the world’s highest-paid DJs for six consecutive years from 2013 to 2018, thanks to his lively, energetic, crowd-pleasing music — spanning genres from EDM to funk.
Justin Timberlake – $250 million
It could be argued that Justin Timberlake has Disney to thank for his career. He started out as a member of The All New Mickey Mouse Club in the early 1990s, appearing on the popular show alongside future stars Britney Spears, Christina Aguilera, and Ryan Gosling.
Since then, he has made pop history as a member of boyband NSYNC and as a solo artist, winning numerous accolades including 10 Grammys, four Emmys, three Brit Awards, and nine Billboard Music Awards.
Herb Alpert – $250 million
Whilst his name may not be as recognizable as some of the pop stars on the list, Herb Alpert’s musical legacy is incredible. A successful jazz artist and trumpeter, he founded The Tijuana Brass band in the 1960s.
However, he has also made a considerable fortune from co-founding reputable label A&M Records with Jerry Moss in the same decade. He has writing credits on many famous songs, such as “Baby Talk” by Jan and Dean, as well as Sam Cooke’s “Wonderful World.”
Phil Collins – $260 million
Phil Collins is a multi-talented man. He’s a drummer, singer, songwriter, producer, and actor — who made his name in the 1970s as part of rock band Genesis. His drumming style has influenced percussionists all over the world, with stars such as Foo Fighters’ Taylor Hawkins citing Collins as an inspiration.
Alongside Paul McCartney and Michael Jackson, he is one of only three recording artists who have sold over 100 million records worldwide as both a soloist and a band member.
Lady Gaga – $275 million
Lady Gaga is a household name known for her outrageous outfits, elaborate music videos, and powerful voice. Ever since the release of her debut album in 2008, Gaga has captured the public’s attention.
Whether she’s making headlines for wearing a dress made of meat or raising money for her non-profit organization — The Born This Way Foundation — she is always in the press. Nonetheless, her musical talent speaks for itself, making her the fourth highest-earning female musician of the 2010s.
Mick Jagger – $300 million
From a pop diva to a rock legend, Rolling Stones leading man Mick Jagger is another musical icon. His bold stage presence, gravelly voice, and songwriting talents have earned him a place in the Rock and Roll Hall of Fame.
At the age of 77, he’s still recording music and touring. Jagger’s influence on popular culture is significant, as his music defined a generation. He was even the subject of a series of paintings by famous artist Andy Warhol.
Michael Jackson – $350 million
Michael Jackson is one of the most famous solo artists ever, so it’s no surprise that he is also one of the highest-earning. Having made his name as part of the family band The Jackson 5, his fame skyrocketed in the late 1970s and early 1980s.
It was during this time that he released a host of successful singles from his debut solo album Off the Wall, including “Don’t Stop ‘til You Get Enough” and “Rock With You.” He’s called ‘The King of Pop’ for a reason!
Sting – $500 million
Gordon Matthew Thomas Sumner — known by the catchier stage name of Sting — is an English musician, songwriter, and actor. His band, The Police, was one of the biggest acts of the 1980s. Following their split, he launched a fruitful solo career.
His most famous song, “Every Breath You Take,” has been remixed and covered by countless artists, and in 2002 he was awarded the Ivor Novello Award for Lifetime Achievement from the British Academy of Songwriters, Composers, and Authors.
George Harrison – $400 million
It could be argued that The Beatles is the most famous band of all time. Hailing from Liverpool, their music reached a global audience and had a major impact on the development of pop and rock music.
Whilst his bandmates, John Lennon and Paul McCartney, often receive the most praise, Harrison was an integral part of the band and wrote many of their hits. Following his untimely passing in 2001, he left a considerable fortune due to his incredible career.
Jimmy Buffett – $400 million
Despite the fact that he was born on Christmas Day, Jimmy Buffett’s music is all about life in a summery, tropical island paradise. His feelgood music has made him an American national treasure, with songs like “Margaritaville” and “Cheeseburger in Paradise” selling millions of copies across the country.
He is also a savvy businessman, owning a chain of popular restaurants inspired by the island lifestyle featured in the lyrics of his songs. He’s the king of Caribbean rock and roll!
Dolly Parton – $450 million
Her unforgettable songs have made her a country music icon — everyone knows the words to “9 to 5,” “Jolene,” and “Here You Come Again.” You may be forgiven for thinking that “I Will Always Love You” is a Whitney Houston classic, but Dolly actually wrote and originally performed the track!
These hits have made her a household name, earning her place in the Country Music Hall of Fame. Her career began in 1956 and is still going strong. Go, Dolly!
Jay-Z – $475 million
Rappers are known for boasting about their wealth and success, and Jay-Z has definitely earned his bragging rights. Not only is he part of one of the music industry’s most famous power couples (#TheCarters!), but he has also carved out an illustrious career as a rapper, songwriter, businessman, and producer — spanning four decades.
He holds the record for the most Grammy awards held by any rapper, and he has sold over 50 million albums worldwide. You simply can’t knock his hustle.
Mariah Carey – $500 million
Mariah Carey is the ultimate pop diva. She signed to Columbia Records in 1988 and released her eponymous debut album two years later. She is known for her incredible vocal range and impressive whistle register.
She was inducted into the Songwriters Hall of Fame for her contribution to the contemporary pop and R&B genres, with her many hits including “Emotion,” “All I Want for Christmas Is You,” “Hero,” and “Fantasy” — influencing many of today’s popular artists, such as Ariana Grande.
Elton John – $500 million
Elton John is world-famous for his heartfelt piano ballads, selling millions of copies across the globe. In the 1960s, he initially worked as a songwriter and session player for other musicians, until the release of his debut album, Empty Sky, in 1969.
He didn’t achieve mainstream success until his second album, with its first single “Your Song” reaching the top ten in the UK and US. He has also written for musicals including The Lion King and Billy Elliot.
Sean Combs – $550 million
Also known professionally as P-Diddy, Puff Daddy, Puffy, and Diddy, Sean Combs is a man of many names and many talents. His impressive resume lists the job titles of rapper, record label executive, producer, singer, songwriter, and actor.
As a result, he’s one of the wealthiest men in the music industry. Through both his own music and his work with other artists — such as Mary J. Blige and Notorious B.I.G — he has revolutionized the hip-hop genre throughout his career.
Bono – $600 million
The frontman of Irish rock band U2, Bono is a highly influential singer, songwriter, actor, and philanthropist. His musical journey began as a schoolboy in Dublin, after he responded to an ad posted by classmate Larry Mullen Jr, who was looking for musicians to start a band with.
After a few line-ups and name changes, U2 was born. They rose to success throughout the 1980s, with albums such as The Joshua Tree and The Unforgettable Fire selling millions of copies.
Paul McCartney – $800 million
Paul McCartney’s musical legacy is difficult to summarize in a few words. As part of The Beatles, he wrote some of the most iconic pop songs of all time including but not limited to “Penny Lane,” “Can’t Buy Me Love,” and “Love Me Do.”
He has also released several successful albums as a solo artist and member of the band, Wings. A truly eclectic and diverse artist, McCartney loves collaborating with other musicians such as Johnny Cash, Elvis Costello, and even Kanye West.
Andrew Lloyd-Webber – $1.2 billion
This next one may surprise you. It’s not held by a legendary rockstar or pop diva — this songwriter has made his millions from transforming the world of musical theater.
Andrew Lloyd Webber is the man behind iconic stage shows such as Cats, Jesus Christ Superstar, Evita, The Phantom of the Opera, Starlight Express, and Joseph and the Amazing Technicolor Dreamcoat — amongst many others. Without him, London’s famous West End would be a very different place.
Bob Dylan – $200 million
A truly iconic figure in folk music history, Bob Dylan is known for his distinctive voice and emotive, politically-charged songs. His most famous compositions include “Hurricane” and “Blowin’ in the Wind,” which have been closely linked with protest movements.
Perhaps his most famous song, “Times They Are a-Changin” has been adopted by humanitarian and pro-civil rights causes. In 2016, he was the first musician to be awarded the Nobel Prize for Literature for his impact on American culture and tradition.