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Famous Hollywood Entrepreneurs

Updated on October 5, 2022
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Mack Sennett

Mack Sennett; Creator of The Keystone Cops and Bathing Beauties

Mack Sennett was born in Quebec Canada on January 17, 1880 and christened Michael Sinnott. His parents were Irish Catholic immigrants who left their home country due to strangulating high taxes and wished to find a place in which they could start a business and keep a fair amount of their own money. They cherished the American dream but tried their luck in Canada, which provided more freedom than Ireland for the Sinnott family but its nearness to the United States was its best attribute. When young Michael Sinnott was only 17 the family moved to Connecticut, where the families hard work paid off and they began to prosper. Michael decided to pursue his dream and become an opera singer, but his family, still reeling from the stifling socialism that they had wanted so desperately to escape, wished for their son to find a more respectable and stable way to earn a living.

Sinnott had a natural flare for show business, changing his name to Mack Sennett because it looked better and "flowed". He then launched himself full throttle into his chosen profession, as an actor, clown, dancer and singer. Sennett's game plan was to be seen often and to get as much experience as possible. Movies were taking over, and the stage actors were losing favor to film actors. Sennett had gained the respect and trust of Adam Kessel and Charles O. Bauman, co-owner's of New York Motion Picture Company, and when Sennett talked up the idea of starting his own company in Edendale California, just a few miles away from Hollywood, the two men backed Sennett and his ambition of launching his own studio. Mack Sennett understood that his one possible way of winning in life would be to take a system that is already in place and imitate it. The foundation of a businessman.

Sennett built "The Keystone Studios" just outside of Hollywood. He focused on comedy and continued to study what people liked to see and what they found funny. Sennett created the Keystone cops because he discovered that people liked to see authority figures look foolish. He also found that beautiful women wearing fashionable bathing suits could easily draw an audience, he created the Keystone Bathing Beauties. Mack Sennett was soon known worldwide for his Keystone cops and bathing beauties film shorts.

Sennett worked relentlessly turning out numerous comedies and launching the careers of many stars such as Marie Dressler, Mabel Normand, and Anita Page. By 1915 he was a respected director and businessman, so much so that he joined forces with Thomas Ince and D.W. Griffith to form the Triangle Company. In 1917 Sennett sold the Keystone trademark and embarked on a new venture; The Mack Sennett Comedy Corporation.

During the 1920s his films had gained polish and were in high demand. Sennett was a hard worker and relentlessly pushed on for bigger and better things unfortunately when the great depression hit and FDR began pushing the New Deal, independent entrepreneurs who often swung on a shoestring had no fighting chance against the big money and power of larger business teams. Sennett's projects drifted into obscurity, but he kept afloat by writing and living off of his celebrity status. In later years just before his death in 1960 at the age of 80, a party was thrown in his honor. The modern Hollywood men who were in charge of the entertainment brought on a slew of girls clad in skimpy bikinis in honor of Mack Sennett's bathing beauties.
Ever the gentleman, Sennett gave an animated yawn before explaining, "the bathing beauties I introduced were in no way meant to degrade women. The suits they wore were stylish. These suits they wear today leave nothing to the imagination, that is why I yawned. "

Young Charlie Chaplin

"The Little Tramp" Charlie Chaplin

One of the most famous figures in the world is such a fixture to people of all ages that one can easily forget that Charlie Chaplin was once a flesh and blood man who struggled his way out of London poverty into an American multimillionaire. Born into the Victorian slums of England in 1889, Charlie Chaplin's mother, Hannah, was a moderately successful stage performer, and his father, Charlie Chaplin Senior, was a highly successful comedian of the London stage.

When Charlie was very young his parents separated, with Hannah taking charge of young Charlie and a son she had given birth to four years earlier, Sydney Chaplin. Charlie and Sydney did not share the same father and it is doubtful that Hannah was married to the man who impregnated her with her first son. The "family" life for the Chaplins' was in no way the traditional American ideal; with loving parents and a supportive unit, but was a rather liberal one, comparable to the modern family. Hannah had children and it was considered to be her responsibility, while Charles Chaplin Sr, caroused, spent his substantial money on himself and his mistresses, while Hannah struggled to find work in sweat shops. As Charlie and Sydney grew older, they would pool their money to help their mother, who had suffered from malnourishment, eventually being sent to a mental hospital.

Chaplin worked tirelessly, taking jobs as a boy actor whenever he could, and working as an errand boy when acting jobs were nil. Even in London of the 19th century, Charlie was thinking big and wanted to reach the highest heights of living. As luck would have it, he got a solid job working for Fred Karno as a comedian. The company went on an American tour and while on tour Chaplin was spotted by Mack Sennet, who was anxious to replace his top comedian Ford Sterling. Mack signed Chaplin and his appearances in motion pictures so impressed audiences that they began asking to see more of him. Although Chaplin was thrilled with the huge salary he was receiving under Mack Sennet, he was anxious to earn even more. He opened his own studio and began acting, producing and directing his own movies.

Chaplin became one of the greatest success stories that Hollywood has ever produced. In the days of silent film creativity, and uniqueness were king, and Chaplin's films continued to improve during the late teens and through the 1920s. In his early days, while his main focus was on making money, he turned out twelve films in one year, but as his popularity grew, and he became a very rich man, and lavished years on the making of a single picture. Once he became a master film maker, Chaplin personally composed music for all of his films. One particularly well known piece was titled, "smile". He was the ultimate entrepreneur who wanted to conquer every challenge that life had to offer. Strangely, his political leanings were strongly to left which led many to feel suspicious of his motives. For why was it okay for he to earn great wealth by hard work and talent, yet he romanced liberal ideas that the lower class be limited. The frequently criticized McCarthy era was in full swing shortly after WWII. After the atrocities of natzi Germany America was determined to keep America free of public figures who preached harmful rhetoric that would hurt the future freedom of the country. Chaplin was suspected of being a communist sympathizer and when he refused to be questioned on his views was no longer considered welcome in the United States. He moved to Switzerland where he settled down to a very idealized American lifestyle where he would father eight children with his wife, Oona O'Neal well into his old age. On Christmas day 1977 Chaplin died at the age of 88 in a 35,000 acre Swiss home. A far cry from the slums in which he was raised.

Mary Pickford

America's Sweetheart

Charlie Chaplin wrote in his autobiography that Mary Pickford was such a brilliant business woman that it disturbed him. Charlie was a liberal minded man who thought that business sense and independence was unattractive in a woman. Unattractive or not, Mary had business sense in spades, and there were plenty of men who found her intelligence irresistible. Here was this beautiful woman who played loveable and innocent characters on the screen and was in real life a shrewd woman with a sense of her own future. She was born Gladys Smith on April 8, 1892 in Toronto Canada and had two younger siblings, Jack and Lottie.

They lived a simple and traditional life with their father working a variety of odd jobs when suddenly everything changed as their father died of a blood clot in 1898. Young Gladys' mother, Charlotte Smith, began working as a seamstress and took in boarders to keep food on the table. One such house guest was a stage manager who saw potential in the 7 year old Gladys and the precocious youngster was given small roles on the stage. After experiencing moderate success her brother and sister were also recruited to the stage.

By 1903 they were a traveling stage family and in 1906 Gladys was a seasoned actress who was receiving serious parts on the Broadway stage. It was around this time that she changed her name to Mary Pickford at the insistence of David Belasco, the man who produced some of her most important stage roles. After completing a major tour one of Mary's plays had reached an end and she was out of work in 1909. Not one to wait around and hope for a miracle Mary went to the Biograph company that was turning out movies in search of extra work so that she could make some money until landing another major part on Broadway. During the early 1900s well respected stage actors would not lower themselves to motion pictures but Mary, realizing that this was an entirely new medium with the potential to reach the whole world decided to try her luck.

The great D. W. Griffith gave Mary a screen test in which she lost the part she tried out for but gained the respect of the great director. He paid his actors $5 per day which was great pay for the time, and realizing that Mary was an experienced actress he hired her and gave her $10 per day.

After gaining celebrity status Mary demanded a higher salary and over the next decade she moved to several different studios demanding higher salary at each. By her early 20s she was earning over $300,000 per picture. As she continued to develop super star status she sold her story lines and gained artistic control of her films; demanding that her films be distriubuted independently.

Mary's trademark was her beautiful long golden hair that was styled in finger waves that graduated into long curls. There were numerous stars who copied her hair but none wore the style as well as Mary did. Her crowning glory can be compared to Farrah Fawcett's in the 1970s. Just about every woman was copying it in some form. When Mary decided that she needed to move on to more modern and sophisticated roles she was shrewd enough to cash in on having her hair cut.

The 1920s flapper was gaining popularity and all the big stars were jumping on the band wagon to have their hair bobbed in the flapper style. Mary wanted to shed what was quickly becoming an outdated look and at the same time give herself a new modern image. She called reporters to photograph and write stories about her trip to the beauty parlor.

Mary worked the media of the 1920s like Donald Trump works the media today. Audiences flocked to see Mary's new look and adjust to her new style.

In 1919 she divorced her husband Owen Moore and married Douglas Fairbanks. She then partnered with Doug, Charlie Chaplin and D.W. Griffith to form their own company called, United Artists.

Mary continued to make movies in the 1920s but had slowed down her pace considerably. She made a few more talkies before retiring from the screen to devote her time and energy to charities and fundraisers.

The Business Man Comedian

Harold Lloyd

Born in Nebraska on April 20, 1893. His father, nicknamed "Foxy", was forever searching for a way to make millions while his mother tried to live a more simple and routine life. Harold Lloyd was greatly influenced by his father and when the strain of uncertainty caused his parents to separate, Harold stayed with his father while his older brother Gaylord stayed with his mother.

At the age of 12 Harold began taking acting jobs on the stage and after "Foxy" made good on an accident involving a truck that hit him while crossing the street, the two took the cash settlement and moved to California. The two men would take a portion of the cash and leverage it. Foxy opened up a Saloon that featured pool tables while young Harold attended High School and focus on drama courses.
It was not long before the two men were flat broke leading Foxy to suggest Harold try to get a job as a movie actor as the two lived in San Diego and it just so happened that the Edison Company was shooting a film in downtown San Diego. As luck would have it Harold met Hal Roach on his very first day of filming. Roach already had plans in his back pocket to become a major producer and he informed Lloyd that once he had his own studio he would make him a big star.

Soon Roach opened his own company called Phun Philms, and later renamed it Rolin. After Roach bought out his partner he contacted Lloyd tomake good on his promise to star him in comedies. Being the big fish in the little pond was a great way for Harold to gain notoriety and confidence in the new medium. He was given full creative control and eventually came up with a comedy character named, Lonesome Luke. The character was an obvious Charlie Chaplin knock off, but through the repetition of turning out reel after reel, Lloyd's creative juices were stirred.

It is unclear how Harold Lloyd eventually dropped his Lonesome Luke character and developed what was to become his trademark of horn ripped glasses and the look of an every day man. Lloyd was unique in that during the early part of the 20th century comedians had a funny or comic look. Lloyd was the first to look normal.

He soon left Roach and started his own studio, where he was the producer, director and star of his feature films. Lloyd employed both is brother Gaylord and his father to manage his financial affairs and went on to become one of the wealthiest Hollywood stars living in Beverly Hills. Lloyd was at the height of his fame in the 1920s and tapered off during the late 20s, retiring after making a few successful talkies. Harold and his wife Mildred spent the 1930s and 40s raising their family, assisting in charities by opening their home to Veterans, and having parties.

Harold Lloyd & Harold Lloyd Jr.

Dick Powell

The Wise Crooner

Dick Powell was born November 14, 1904 in Mountain View Arkansas. He became a singer in the early 1920s, singing with the Charlie Davis Orchestra and even cutting a few records. Powell moved to Pittsburgh for unknown reasons in the 20s and due to his natural charm along with a pleasing tenor voice he made a local success of himself as a Master of Ceremonies at one of Pittsburgh's biggest theaters. Powell was now entertaining on weekends and signed with the Vocalion record label. In 1930 Warner Brothers bought out Vocalion and were so impressed with Powell's charming stage presence and singing voice that they signed him to a film contract. Powell was introduced to American audiences in the movie, Blessed Event in which he basically imitated his stage style from the Pittsburgh theater. Shortly after making his film debut he was cast as a lead actor in the huge success 42nd Street and his film career took of like a bullet.

Powell made a string of films such as Gold Diggers of 1933, Flirtation Walk, and Footlight Parade. He was blessed with a cute and boyish style that appealed to audiences of the early 1930s, and his persona was unlike any male star ever since. He was every girls dream boyfriend; handsome, classy, respectful, charming and romantic. His movies were popular and to compound his success in musicals, his records sold by the thousands. Powell's persona was one that could not last however, it was the personification of youth and innocence and being an entrepreneur at heart Powell knew that if he were to let Warner Brothers keep control of his career he would be a has been within ten years. As his youth deteriorated Powell fought for challenging parts that were far and away from the lovable teddy bear he had been playing. He lobbied to play the lead role in Double Indemnity with Barbara Stanwyck, but the role eventually went to Fred MacMurray who was a huge success in the film. This further fueled Powell to pursue other roles along the same lines. He believed that in the part of a tough guy his image could be remade and thus his career would have longevity.

His break came in 1944 when he landed the role of Philip Marlowe in Murder My Sweet. Powell played a hardened detective who bore no resemblance to the former smiling and singing Dick Powell of Warner Brothers Musicals. Powell's career was jump started once again and he could play in movies well into advanced age with the new image that he had created. But Powell never put all of his eggs in the same basket. He invested in real estate; flipping houses, buying and holding enormous mansions and then selling when the market took off again. To keep his career thoroughly diversified he began directing and producing too.

Dick Powell kept his mind open to other business ventures and discovered that real estate investing was one of the easiest ways for average Americans to leverage their incomes. Powell continued to flip homes and profited greatly in real estate before passing at the age of 58 from throat cancer.

Bob Hope


Bob Hope was born May 29, 1903 in Eltham London England. He was the 5th of 7 sons to a family of vaudevillians. The family immegrated to the United States in 1908 and and settled in Cleveland Ohio. Bob learned to tap dance, sing and tell jokes like a pro by the age of 12 and in 1915 he won a cash prize for his impersonation of Charlie Chaplin. Hope also attended the Boys Industrial School in Lancaster, Ohio as he took odd jobs as a butcher and a lineman to earn a living.

A popular and charming young man, Hope had a steady girlfriend and it was while dating her that the two decided on show business for a living and they took dancing lessons together and choreographed routines. In 1925 Roscoe "Fatty" Arbuckle saw hope and members of his dancing team performing and he hooked them up with the Hurley's Jolly Follies, several months later Hope formed a team called the Dancemedians. They were a team of vaudeville performers, tap dancers and comedians. Hope had been moderately successful for five years in the vaudeville and stage performers circuit and decided to give films a whirl. He made a screen test for Pathe in 1930 but was turned down but Hope did not give up. He went on to radio and then to New York where he made a series of short films for Educational.

By the early 1940s Bob Hope was a thoroughly well rounded actor now accepted by Hollywood as his career really took off. Hope may not have been accepted by Hollywood right off the cuff but he forced his presence upon the film industry by becoming a familiar voice on radio and in the lesser known movie companies to which Hollywood would have to respond had he become a big enough success. Soon Bob Hope was paired with Bing Crosby in the famous "Road" movies, along with countless guest appearances and radio spots. Hope also became a regular host at the Academy Awards Ceremonies for 15 years straight. Bob Hope's relationship with Bing Crosby was purely a business one. They invested in oil wells, real estate and other businesses together, and as Hope came into his own at the beginning of WWII he began putting on special shows for the soldiers which soon led to his family and then other celebrities joining him on USO tours. Bob Hope was a crusader for the men who were putting their lives at risk during the war.

Hope started playing golf in the 1930s and became such a perfectionist in his chosen sport that in his prime he was playing with a 4 handicap. Hope eventually played well over 100 charity events and in 1960 The Bob Hope Classic was born, Which made history when in 1995 Hope created a foursome of Gerald Ford, George W. Bush and Bill Clinton.

Bob Hope accumulated enormous wealth through the purchase of real estate. In the 1940s he purchased large parcels of land in the Beverly Hills and Hollywood area after taking note of the vast number of people moving to California to be near Hollywood.

Desi Arnaz

Lucy and Desi

The Cuban Who Embraced America

Desi Arnaz was born March 2, 1917 in Santiago de Cuba, Cuba. His father was a respected citizen who became the cities youngest mayor and a member of the house of representatives. Due to the hard work and discipline of his family they owned three ranches, a beach home and a mansion on the main land. The family were robbed of their property during the Cuban revolution of 1933 when democrat socialist Fulgencio Batista came into power. Desi was a lifelong Republican after seeing the hypocritical and damaging theft and violence of the left wingers. After the Arnaz family were robbed by the government Alberto Arnaz senior was jailed for six months while the dictators established a firm footing on the country. After Alberto's brother-in-law pressed the new government for six moths Alberto was released and the family immediately fled to Miami Beach Florida. Young Desi attended Catholic schools and worked hard to learn English and Desi realized that the quickest way to gain something in this foreign land was to head straight for the entertainment industry.

With his intense good looks, personality and talent Desi was a shoe in as a bandleader, extra in Hollywood. He was given a few parts that capitalized on his good looks and during the 1940s when Latin dancing was the rage Desi was in the right place at the right time.

Desi was not hurting for money. As soon as he got his feet planted in the United States the sky would be the limit. He created his own orchestra, traveled the country, and even married movie star, Lucille Ball. After years of show business he and Lucy decided that rather than he travel with his band and she try out for parts, they would pull their talents together and appear on their own television show, I Love Lucy. The show turned out to be the most popular television show of all time. But, Desi was the master mind who created Desilu productions in which he profited on many other shows of the 1950s.

Desi retired to real estate ownership, and said that this country allowed him to be a success and after the tragic communist uprising of Cuba, he was deeply grateful to the U.S. A.

This content reflects the personal opinions of the author. It is accurate and true to the best of the author’s knowledge and should not be substituted for impartial fact or advice in legal, political, or personal matters.

© 2014 Glenda Goddard


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