The romance sounded like the beginning of an old Hollywood fairy tale.
One of America’s most beloved entertainers had recently become a widower. The beautiful blonde entering his life was a rising model and television performer, already celebrated for her warmth and resemblance to the screen’s most famous women.
Their relationship reportedly became serious.
He proposed marriage.
But she did not become his second wife.
Follow @allchronologyIn a twist that would have stunned even Hollywood’s most imaginative screenwriters, she later walked down the aisle with his son.
Long before entering one of entertainment’s most famous families, she was a working-class girl from San Francisco.
Born in 1931, she grew up with two brothers. Her childhood contained an early tragedy when her older brother Arthur, a promising baseball player, entered military service during World War II. He was killed after the bomber on which he served was shot down over Germany.
For the young girl left behind, public recognition arrived through an entirely different route.
In 1949, she won a local competition carrying the wonderfully wholesome title “Miss Milkmaid.” The crown led to public appearances and opened the door to further beauty contests.
A year later, she became Miss San Francisco.
She reportedly secured the title by performing a dramatic monologue rather than relying solely on physical appearance. In 1951, she advanced to the Miss California pageant, where she finished sixth.
Her personal life was already moving quickly.
At 19, she married George von Duuglas-Ittu in Nevada. Their son was born later that year, but the marriage ended in divorce in 1954.
By then, Hollywood had begun noticing her.
Howard Hughes—the eccentric billionaire, filmmaker and aviation pioneer—reportedly discovered the striking blonde and signed her for appearances in productions connected to his studio interests.
She appeared in The French Line, a musical built around Jane Russell and marketed with the kind of sensuality that made censors nervous. She also entered the exotic spectacle of Son of Sinbad, another Hughes production whose release was delayed partly because of objections to its revealing costumes.
The roles were often small and uncredited.
But the camera loved her.
She appeared as a handmaiden, harem girl, model, dancer and glamorous background beauty in films such as The Adventures of Hajji Baba, Kismet, Daddy Long Legs, Man with the Gun and Guys and Dolls.
For the latter, she reportedly worked as one of the Goldwyn Girls—an elite group of dancers selected as much for visual glamour as for their ability to perform.
Television offered her a greater opportunity to develop a recognizable identity.
She appeared on Queen for a Day, The Colgate Comedy Hour, The Jimmy Durante Show, The Milton Berle Show and The Chevy Show. In 1956, NBC signed her to a contract, an unusual achievement for a performer whose movie appearances had largely consisted of small parts.
The network invested in her development.
Oscar-winning actress Agnes Moorehead reportedly coached her in acting, while celebrated composer Meredith Willson helped train her voice. The blonde model was being prepared for something more substantial than simply decorating the background.
The press responded with extravagant nicknames.
She was described as “Television’s Marilyn Monroe,” “the Blonde Rita Hayworth” and even “the Rich Man’s Jayne Mansfield.” Each comparison reflected Hollywood’s habit of defining an emerging woman through the image of someone already famous.
But her private connections soon became more intriguing than any studio publicity campaign.
She was linked romantically to several recognizable men, reportedly including Frank Sinatra and actor Rod Taylor.
Then Bing Crosby entered the story.
Crosby was one of the most successful entertainers of the 20th century, a relaxed singer and actor whose voice had become inseparable from American popular culture. His first wife, Dixie Lee, died from ovarian cancer in 1952, leaving him a widower with four sons.
Follow @allchronologyAccording to later accounts, Crosby began dating the young blonde sometime after his wife’s death. Their relationship grew serious enough that he reportedly proposed.
She declined—or the relationship otherwise failed to reach the altar.
Years later, the story acquired its astonishing final twist.
While performing as a showgirl at the Tropicana in Las Vegas, she became involved with Dennis Crosby, one of Bing’s twin sons. On May 4, 1958, they married at the same hotel.
The woman once considered as a possible second wife for Bing Crosby had become his daughter-in-law.
Dennis adopted her child from her first marriage, who became known as Gregory Crosby. The couple also had two sons together, Dennis Jr. and Patrick Anthony.
But the marriage was not an easy escape into domestic happiness.
Dennis and his brothers had grown up beneath the immense shadow of their famous father. Decades later, the Crosby family’s private struggles—including allegations concerning harsh discipline, alcoholism and emotional pain—would become subjects of public debate.
The marriage ended in divorce in 1964.
Before that, however, she achieved one final burst of pin-up fame.
In October 1958, only months after marrying Dennis, she appeared as a Playboy Playmate of the Month. In an unusual first for the magazine, she shared the monthly distinction with actress and model Mara Corday.
Her centerfold was photographed by Sam Wu.
Decades later, that photograph appeared briefly in the Clint Eastwood film Space Cowboys, creating an unexpected final connection between her 1950s image and a new century of movie audiences.
Her own film career had already ended with a small appearance in the 1958 musical Gigi.
She gradually withdrew from entertainment. In later years, she reportedly worked for Gucci and lived in Beverly Hills with her longtime friend Gloria Haley, the daughter of The Wizard of Oz actor Jack Haley.
Follow @allchronologyShe survived cancer but died from a heart attack in January 2006. She was 74.
Her journey had begun with a “Miss Milkmaid” crown and carried her through beauty pageants, Howard Hughes productions, network television, Las Vegas showrooms and the complicated private world of the Crosby dynasty.
Yet one extraordinary detail continues to make her story irresistible.
The San Francisco beauty who was reportedly proposed to by Bing Crosby before marrying his son Dennis was Patricia Ann “Pat” Sheehan.
