Bob Hope was the epitome of a show business icon. For nearly a century, he dominated entertainment—starring in vaudeville, radio, film, and television. He hosted the Academy Awards a record 19 times, brought laughter to millions with his quick wit, and dedicated much of his life to entertaining U.S. troops overseas. His influence spanned generations, making him one of the most enduring figures in 20th-century entertainment.
However, while the world knew him as a comedy legend, few realized he had another remarkable skill: accumulating immense wealth.
Beyond the spotlight, Bob Hope quietly built a financial empire, making strategic investments that left even Hollywood’s biggest players in awe. Though his name was synonymous with humor, behind the scenes, his fortune was growing in unexpected ways.
Early Life & Career Beginnings
Born Leslie Townes Hope in Eltham, London, on May 29, 1903, he was the fifth of seven children. In 1908, his family immigrated to the U.S., settling in Cleveland, Ohio.
To help his family financially, Hope performed on streets and in streetcars, singing, dancing, and telling jokes for spare change. His talent led him to enter various competitions, and in 1915, his Charlie Chaplin impersonation won him a prize. During his teenage years, he worked in different jobs, including as a butcher’s assistant and a lineman. However, he missed performing and decided to pursue it professionally.
Hope took dance classes with his girlfriend, and together, they developed a routine that earned them $8 per night. When their act ended due to her mother’s disapproval, he partnered with Lloyd Durbin. Their performances impressed silent film star Fatty Arbuckle, who recommended them for the touring vaudeville company Hurley’s Jolly Follies. From there, Hope formed his own act, the “Dancemedians,” and toured with George Byrne and the tap-dancing conjoined Hilton Sisters. He also briefly performed a “Siamese twin” act in blackface with Byrne, but it was quickly abandoned in favor of his more successful stand-up routines.
Broadway Breakthrough
Hope’s success in vaudeville led to Broadway opportunities. He and Byrne were cast in Sidewalks of New York, starring Ruby Keeler. As they toured, Hope began introducing acts before performances, and audiences loved his humor. By the time they reached Pennsylvania, he had become a solo act.
He attempted to break into Hollywood in 1930 but found little success and returned to Broadway. Between 1932 and 1936, he appeared in productions like Ballyhoo, Roberta, Say When, Ziegfeld Follies, and Red, Hot, and Blue. Around the same time, he began appearing in short comedy films for Educational Pictures.
Rise to Radio Fame
Hope transitioned to radio in 1934, and by 1937, he had signed a contract with NBC to host the Woodbury Soap Hour. This led to a 10-year contract for The Pepsodent Show Starring Bob Hope, which paid him $2,500 per week. Out of his salary, he personally covered the costs of his writing team, which grew to 15 as the show’s popularity soared.
Hollywood Stardom
Hope’s radio fame, Broadway success, and comedic shorts finally caught Hollywood’s attention. Paramount Pictures signed him, and he made his film debut in The Big Broadcast of 1938, which featured what would become his signature song, Thanks for the Memory.
From there, his career skyrocketed. He starred in over 70 films, won numerous honors—including the Jean Hersholt Humanitarian Award and four honorary Oscars—and hosted the Academy Awards a record 14 times. His Christmas TV specials captivated audiences, with over 60% of the nation tuning in annually.
Hope also dedicated himself to performing for U.S. troops. As a USO entertainer from 1941 to 1991, he traveled the world, bringing joy to soldiers. His contributions earned him the Congressional Gold Medal, the Presidential Medal of Freedom, the National Medal of the Arts, and honorary membership in the U.S. Armed Forces in 1997.
A Fortune Built on Real Estate
As his earnings grew, Hope began investing in real estate—a decision that would ultimately make him one of the richest entertainers of all time.
A well-known story recalls Hope hiking with Bing Crosby in the 1940s. While overlooking the undeveloped San Fernando Valley, Crosby remarked:
“This is the Beverly Hills of tomorrow.”
Inspired, Hope began purchasing large amounts of land wherever he saw potential. His daughter, Linda, later noted:
“The way some people collect stamps or rare coins, Bob Hope collected property.”
Over the decades, Hope’s portfolio expanded to include ranches, subdivisions, and commercial properties across California and beyond.
In 1967, Time Magazine reported that he owned 8,000 acres in Palm Springs, 4,000–5,000 acres near Phoenix, and 7,500 acres in Malibu—claiming his holdings were 50 times the size of Monaco.
By 1983, Forbes ranked Hope among the 400 richest Americans, estimating his net worth at $200 million (approximately $640 million today). Hope, however, dismissed the estimate, saying:
“If my estate is worth over $50 million, I’ll kiss your ass. I mean that.”
Forbes later revised their estimate to $85 million, but Hope never made good on his promise.
By the 1990s, he had sold much of his real estate empire. At the time of his passing in 2003, his net worth was approximately $150 million (around $250 million today). His estate retained two of his most prized properties:
Palm Springs Mansion
Hope’s iconic Palm Springs home, designed by modernist architect John Lautner, was a futuristic 23,366-square-foot estate featuring a concrete dome, panoramic desert views, and a skylight resembling a volcano’s crater. It included 10 bedrooms, 13 bathrooms, a pool, tennis courts, and putting greens.
Despite its architectural fame, the mansion struggled to sell. Originally listed at $50 million in 2013, it eventually sold in 2016 for $13 million to billionaire Ron Burkle.
Toluca Lake Estate
Hope’s 5.2-acre Toluca Lake estate was his home from 1939 onward. Originally a Tudor-style residence, it expanded into a 15,000-square-foot mansion with eight bedrooms, a private golf hole, a movie theater, and a vault storing decades of his jokes.
After his wife Dolores passed in 2011, the estate was sold for $15 million, again to Ron Burkle. Burkle restored the property, and in 2022, it resold for $26 million, setting a San Fernando Valley real estate record.
Legacy
Bob Hope’s impact extended beyond wealth and real estate. He was a master entertainer, a philanthropist, and a shrewd businessman. His investments, both in property and in people, left a lasting mark.
Hope’s ability to captivate audiences spanned generations, and his dedication to entertaining troops made him a national treasure. As Nancy Reagan once said, he was “America’s most honored citizen and our favorite clown.”
While his fortune was impressive, his true legacy was the joy he brought to millions—something money could never buy. But, as Hope proved, making a fortune along the way wasn’t a bad thing either.
