Crooning Through History: Bing Crosby’s Hollywood Stardom and Rancho Santa Fe Roots

by Debbie L. Sklar

Bing Crosby, one of the most beloved entertainers in American history, became a household name for his warm baritone voice, magnetic screen presence, and innovative contributions to entertainment. Known for classics like Holiday Inn (1942) and his rendition of “White Christmas,” Crosby’s career spanned more than five decades, reshaping music, film, and television. Yet, away from Hollywood’s spotlight, he was said to have found solace in Rancho Santa Fe, a retreat that reflected his love for golf, family, and a quieter lifestyle.

Trailer for Holiday Inn 1942 via YouTube

A Sanctuary in Rancho Santa Fe

Historians report Crosby fell in love with Rancho Santa Fe in the late 1940s and purchased an expansive estate in this secluded San Diego County community. Far from the glitz and glamour of Hollywood, the property became his family’s haven, complete with a grand home, lush grounds, and a private golf course.

1935 postcard of the home of Bing Crosby in Rancho Santa Fe near San Diego via Ebay .

The nearby Rancho Santa Fe Golf Club held a special place in Crosby’s heart, becoming a favorite spot for him to play with friends. His presence in the area contributed to the tight-knit feel of the community. Crosby’s estate also featured a small recording studio where he hosted intimate gatherings with colleagues and worked on creative projects away from the pressures of his professional life.

Early Life and Rise to Stardom

Born Harry Lillis Crosby Jr. on May 3, 1903, in Tacoma, Wash., Crosby grew up in Spokane as the fourth of seven children in a devout Catholic family. His journey to stardom began when he discovered his passion for music and comedy.

Bing Crosby at 9-years-old, circa around 1912, image from the Radio Mirror, February 1935. Uncredited, Public Domain, via Wikimedia Commons.

Crosby attended Gonzaga University, intending to study law, but his love for music led him to join local bands as a singer and drummer. His big break came when he joined Paul Whiteman’s Rhythm Boys in the late 1920s, performing alongside some of the era’s top jazz musicians. By the 1930s, Crosby’s pioneering use of the microphone as an instrument helped him craft the crooning vocal style that won millions of fans worldwide.

His career exploded with hits like “Pennies from Heaven” and roles in hit films, cementing him as one of the most versatile entertainers of his era.

Bing Crosby singing “Pennies from Heaven” via YouTube

Family Life in Rancho Santa Fe

Crosby’s personal life saw two marriages — first to Dixie Lee, with whom he had four sons, and later to actress Kathryn Grant, with whom he had three children, including actor and singer Harry Crosby. The estate in Rancho Santa Fe provided the ideal backdrop for family gatherings, a peaceful refuge from his almost constant place in the limelight.

Crosby was deeply invested in his children’s lives, and they spent their formative years enjoying the tranquility of Rancho Santa Fe. His ability to balance stardom with fatherhood made him an admired figure both in public and private, according to reports.

Contributions to the Del Mar Racetrack

Crosby’s Southern California connection extended beyond Rancho Santa Fe to the Del Mar Racetrack. A passionate horse racing enthusiast, Crosby co-founded the racetrack in the 1930s. He even personally greeted visitors on its opening day in 1937 as Del Mar quickly became a hotspot for Hollywood’s elite, including stars like Jimmy Durante, due in no small part to Crosby’s involvement.

Bing Crosby at the Del Mar Racetrack when he was also a co-owner with other celebrity friends via YouTube

It is said Crosby also owned several racehorses, deepening his connection to the sport. His association with Del Mar Racetrack added an air of glamour and solidified its reputation as a premier racing destination.

Death and Legacy

On Oct. 14, 1977, Crosby passed away suddenly from a heart attack while playing golf at La Moraleja Golf Course near Madrid, Spain. His death marked the end of an entertainment era, but his legacy lives on through his timeless music, films, and contributions to the entertainment industry.

Gravestone of Bing Crosby at the Holy Cross Cemetery in Culver City via FindaGrave.com

Crosby was laid to rest at Holy Cross Cemetery in Culver City, in the Grotto Section, Lot L-119, Space 1. The cemetery is also the resting place for other Hollywood legends, making it a pilgrimage site for fans.

The Sale of Bing Crosby’s Rancho Santa Fe Estate

After Crosby’s passing, his iconic Rancho Santa Fe estate became a point of interest for fans and real estate enthusiasts alike. The property, set on 210 acres of scenic land, boasted a stately home, private golf greens, and lush surroundings. In 2000, the estate was sold to a new owner, marking the end of its association with the Crosby family.

The sale underscored the timeless appeal of Rancho Santa Fe’s luxurious properties and its association with Hollywood legends. Despite changing ownership, the estate continues to symbolize Crosby’s life away from the spotlight, reflecting the entertainer’s love for relaxation, family, and golf.

Video of The Crosby at Ranch Santa Fe as it is today via YouTube.

Bing Crosby’s Enduring Impact

Crosby remains a cultural icon decades after death and his innovative techniques in recording, acting, and television paved the way for modern entertainment as we know it. As the voice behind “White Christmas,” the world’s best-selling single, Crosby’s influence continues to resonate, especially during the holiday season.

Bing Crosby singing “White Christmas” via YouTube

Crosby’s Rancho Santa Fe estate, along with his involvement in Del Mar and his ties to Southern California, speaks to his multifaceted personality. Whether as a crooner, a father, or a community member, Crosby left an indelible mark that endures in history and memory.

Debbie L. Sklar is a long time contributing editor to the Times of San Diego. For more historical stories about Hollywood’s Golden Age visit here.

Films, TV, Accolades

From several Oscars to many TV shows, here is a link to Crosby’s many projects and achievements.

Sources

Details on Death and Burial – Holy Cross Cemetery

Bing Crosby’s Early Life and Career – Bing Crosby Official Site

Rancho Santa Fe and Estate Details – California Dreaming

Contributions to Del Mar Racetrack – Del Mar Thoroughbred Club

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