Bob Hope was the definition of a show business legend. For nearly a century, he was everywhere—headlining vaudeville stages, dominating radio airwaves, starring in blockbuster films, and cracking jokes on live television. He hosted the Academy Awards a record-breaking 19 times, entertained millions with his signature sharp wit, and dedicated decades to performing for U.S. troops overseas. His influence stretched across generations, making him one of the most enduring entertainers of the 20th century.
But while the world knew him as the king of comedy, few realized he had another remarkable talent: making tons of money.
Beyond the spotlight, Bob Hope quietly built a financial empire, making savvy investments that left even the biggest Hollywood power players in awe. His name was synonymous with laughter, but behind the scenes, his fortune was growing in ways that no one expected.
Bob Hope / Hulton Archive/Getty Images
Early Life & Career Beginnings
Bob Hope was born Leslie Townes Hope in Eltham, London, England, on May 29, 1903. The fifth of seven children, Bob Hope and his family members moved to the United States in 1908. They passed through Ellis Island and then moved on to Cleveland, Ohio, where the family settled down.
In order to make a little extra money for his family, he began performing on the street and in streetcars, earning change, singing, dancing, and telling jokes. He also competed in various talent competitions. His impersonation of Charlie Chaplin won him a prize in 1915. Throughout his teenage years, he worked as an assistant to a butcher and as a lineman. He subsequently decided that he missed performing. However, this time, he wanted to earn more than a little extra money. He enrolled in dance classes with his girlfriend, and they developed an act that soon had them earning $8 per night. After they had to retire their act (her mother did not like it), he joined forces with fellow student Lloyd Durbin. Their performances caught the attention of Fatty Arbuckle, the famed silent film comedian. He recommended them for the Hurley’s Jolly Follies, a touring vaudeville company. From there, he went on to form his own touring act called the “Dancemedians.” Hope toured for a number of years with George Byrne and a pair of conjoined twins who tap danced, known as the Hilton Sisters. He also performed a “Siamese twin” act with Byrne in blackface, but the act was quickly retired because it wasn’t as funny as Hope’s stand-up work.
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Broadway
Hope’s vaudeville career subsequently led to work on Broadway when he and Byrne were cast in the Broadway show, “Sidewalks of New York,” starring Ruby Keeler. At the urging of their agent, they began to work their way west from New York. Along the way, Bob Hope began announcing the coming attractions at each theater where they performed. Audiences ate up his pre-show schtick, and by the time they reached Pennsylvania, Bob Hope had become a solo act. He attempted to launch a screen career in Los Angeles in 1930 without luck, so he headed back to the East Coast, where he continued to work on Broadway. Between 1932 and 1936, he appeared in such Broadway productions as “Ballyhoo,” “Roberta,” “Say When,” “Ziegfeld Follies,” and “Red, Hot, and Blue.” He also began appearing in short comedies for the company Educational Pictures.
Radio Success
In 1934, he started working in radio, as well. By 1937, he had signed a contract with NBC Radio, hosting the “Woodbury Soap Hour.” It was a 26-week contract that led to his signing of a 10-year contract to host the “Pepsodent Show Starring Bob Hope.” He was making $2,500 per week hosting the show, and he paid his eight-member writing team and staff out of his own salary. As the radio program’s popularity grew, so did Hope’s staff, eventually leveling out at 15.
(Photo by UPI/Bettmann Archive/Getty Images)
Major Hollywood Success
His radio work, combined with his success on Broadway and the popularity of his comedic shorts, finally caught the attention of Hollywood. He was invited out west by Paramount Pictures, where he signed a contract and launched his film career with a role in “The Big Broadcast of 1938.” The film featured the song that would become known as his signature number, “Thanks for the Memory.” It was only up from there.
He went on to appear in over 70 films, receiving numerous honors and awards, including the Jean Hersholt Humanitarian Award and four honorary Oscars. He hosted the Oscars a record 14 times, and his Christmas specials for NBC were watched by more than 60% of the nation each year. He also tirelessly performed for US troops, touring as a member of the USO from 1941 to 1991. He received the Congressional Gold Medal, the Presidential Medal of Freedom, the National Medal of the Arts and was made an honorary member of the US Armed Forces by an act of Congress in 1997.
Wealth
As his paychecks grew, Bob began investing in real estate on the side. That side investment would eventually balloon into an empire.
A famous anecdote recalls Hope hiking in the hills above Los Angeles with his close friend Bing Crosby in the 1940s. Gazing over the undeveloped San Fernando Valley, Crosby told him:
“This is the Beverly Hills of tomorrow.“
Taking that cue, Hope began buying up huge swaths of land wherever he saw potential. As his daughter Linda would later recall:
“The way some people collect stamps or rare coins, Bob Hope collected property.“
Over the decades, Hope’s portfolio grew to include ranches, subdivisions, and commercial parcels across California and beyond.
In 1967, Time Magazine published what was thought to be a factual account of his real estate holdings. The article stated that he owned “8,000 acres in Palm Springs, 4,000 to 5,000 acres near Phoenix, more than 7,500 acres in Malibu,” and their list went on. In fact, they believed his holdings were 50 times the size of Monaco.
In 1983, Forbes Magazine added Bob to its list of the 400 richest Americans with a net worth of $200 million. That’s the same as being worth around $640 million today. Bob was not amused with the magazine’s wealth estimate. When he was asked about it soon thereafter, Bob retorted:
“If my estate is worth over $50 million, I’ll kiss your ass. I mean that.“
In the end, Forbes adjusted the magazine’s estimate down to $85 million. Bob did not follow through on his promise to kiss a rear.
By the 1990s, Bob had sold off many of his real estate investments. At the time of his death in 2003, and Bob Hope’s net worth was worth $150 million. That’s the same as around $250 million in today’s dollars. His estate retained two Crown Jewels of his former real estate empire:
- An eye-popping modernist mansion in Palm Springs
- The family estate in Toluca Lake
Palm Springs Mansion
Bob Hope’s Palm Springs mansion, designed by modernist architect John Lautner, became an architectural icon with its dramatic concrete dome and panoramic desert views. Often likened to a mushroom or volcano, the 23,366-square-foot residence featured a massive circular skylight, 10 bedrooms, and 13 bathrooms. Built in 1979 atop six acres in Palm Springs’ exclusive Southridge enclave, it was designed as the ultimate entertainment space for Hope and his wife, Dolores. The expansive grounds included a swimming pool, tennis court, putting greens, and even a boulder that jutted into the living room, blending the home into its rocky hillside setting.
Despite its fame, the mansion struggled to sell after the Hopes’ passing. Originally listed for $50 million in 2013, it remained on the market for three years before billionaire Ron Burkle purchased it in 2016 for $13 million, recognizing its architectural significance.
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Toluca Lake Estate
Bob Hope’s Toluca Lake estate was an expansive 5.2-acre retreat in Los Angeles that served as his home from 1939 onward. The property, originally a 1930s Tudor-style residence, was expanded in the 1950s into a 15,000-square-foot mansion with eight bedrooms, staff quarters, a movie theater, and a personal study. Hope even built his own one-hole golf course, complete with a putting green and sand traps, allowing him to practice without leaving his backyard. The estate also featured swimming pools, formal gardens, a tennis pavilion, and a vault where Hope stored decades’ worth of jokes and scripts.
After Dolores Hope’s passing in 2011, the estate hit the market. In 2018, it was purchased for $15 million, with proceeds benefiting the Bob and Dolores Hope Foundation. Once again, the buyer was billionaire Ron Burkle. Ron carefully restored the home while preserving its historical charm, including Hope’s private study and joke vault. In late 2022, the fully revitalized property sold again for $26 million, setting a record for the San Fernando Valley—a final nod to the legend of Bob Hope.
Legacy
Bob Hope’s legacy is far greater than the wealth he accumulated or the homes he owned. He was a master of entertainment, a philanthropist, and a businessman who understood the value of investing—whether in real estate or in people. His ability to captivate audiences spanned generations, and his dedication to bringing joy to others, particularly through his tireless USO performances, made him a national treasure.
Beyond the laughter, Hope’s success in Hollywood and his real estate empire demonstrated his foresight and ambition. He didn’t just entertain—he built, he invested, and he left behind something tangible. As Nancy Reagan once called him, Bob Hope was “America’s most honored citizen and our favorite clown.” In the end, his influence wasn’t measured in dollars, but in the countless lives he touched—and that’s a legacy no amount of money can buy… but earning a fortune isn’t so bad either.
