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Bing Crosby Had Seven Children with His Two Wives – Meet All of the Star’s Kids

Busayo Ogunjimi
Aug 16, 2022
08:26 A.M.

Remember Bing Crosby? The famous singer and actor was married twice and had seven children during his lifetime. Here is a look at his family.

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Known as the first multimedia star, Bill Crosby is a Hollywood legend. From 1931 to 1954, the star dominated record sales, radio ratings, and motion picture grosses.

He was also married twice and fathered seven children. Here is a breakdown of each of Crosby's children and his marriage to their mothers.

Headshot of American entertainer Bing Crosby | Source: Getty Images

Headshot of American entertainer Bing Crosby | Source: Getty Images

GARY CROSBY

Gary Crosby, the singing legend's lookalike, is the eldest of Crosby's children, born on June 27, 1933, in Los Angeles. His birth name was Gary — after a close friend of his father Gary Cooper.

From a young age, Gary showed that he shared the same passion for entertainment as his iconic dad. At age 9, the Los Angeles native appeared on-screen for the first time, acting as himself in a 1942 production titled "Star-Spangled Banner."

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Gary soon left the movie industry to focus on his education. He graduated from Stanford University before fully launching into the entertainment industry.

Bing Crosby (1903 - 1977) with his wife, actress Dixie Lee and their children Gary, Phillip and Dennis in 1935. | Source: Getty Images

Bing Crosby (1903 - 1977) with his wife, actress Dixie Lee and their children Gary, Phillip and Dennis in 1935. | Source: Getty Images

Bing's firstborn starred in a fleet of TV shows and films, including "A Private's Affairs," "Holiday for Lovers," "The Night Stalker," "Mardi Gras," and "The Bill Dana Show."

Later on, he moved to performing and singing with "The Crosby Boys" from the 1940s to the 1960s, while he worked with his father on two songs, "Sam's Song" and "Play a Simple Melody."

Interestingly, the pair made magic! Gary's album that featured his dad became the first double-sided gold record in history.

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Actor Bing Crosby, his wife Dixie and their firstborn son Gary in 1933 | Source: Getty Images

Actor Bing Crosby, his wife Dixie and their firstborn son Gary in 1933 | Source: Getty Images

While they seemed like the perfect father and son match, their relationship was not as seamless as it appeared. Gary had a turbulent relationship with his dad, and according to his autobiography, the older Crosby was abusive.

In the 1983 publication "Going My Own Way," Gary alleged that his dad was violent towards him. Bing was obsessed about his first son maintaining a certain weight that he checked weekly. Whenever he gained an extra pound, Bing would beat him up with a cane.

Actor and singer Bing Crosby's firstborn son Gary in 1957 | Source: Getty Images

Actor and singer Bing Crosby's firstborn son Gary in 1957 | Source: Getty Images

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Following the book's release, Gary shocked the world with his revelation. But while he made quite a fortune, his family was disappointed at the claims. Mary, his half-sister, thought her half-brother acted greedily but later apologized as she said:

"And Gary said to me that the publishers had told him 'the worse it was the more books will sell.' And he was very clear about why he did it… years later he apologized profusely to us but by then the damage was done."

Unfortunately, Gary's life was cut short in 1995 after he died from lung cancer in Burbank, CA. He was 62 years old. He is survived by a son from one of his three marriages.

Gary Crosby and Dick Clark in 1962. | Source: Getty Images

Gary Crosby and Dick Clark in 1962. | Source: Getty Images

THE TWINS, PHILIP AND DENNIS CROSBY

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Bing's second and third children were twin boys, Dennis and Phillip Crosby. The boys were born on July 13, 1934, in Los Angeles. Robert Trachtenberg, a documentary expert, claimed they might have suffered fetal alcohol syndrome.

Trachtenberg satisfied his curiosity after he showed the boys' photos to USC specialists. They confirmed they looked "like a textbook case of fetal alcohol syndrome."

Despite their physical appearances, the twins performed wonders through their talents. Phillip established himself as an actor who earned minor roles in "Robin and the Seven Hoods" and "None But Brave." However, his movie career was short-term.

Actor and singer Bing Crosby with his wife Dixie and their children | Source: Getty Images

Actor and singer Bing Crosby with his wife Dixie and their children | Source: Getty Images

Although he was born into affluence, Phillip enrolled in the army in the mid-1950s, after his time at the Jesuit-run boarding school in San Francisco. He later attended Washington State University and became an impressive football player.

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When it was time to settle into family life, Phillip did not have a problem. He married the love of his life—twice, with whom he shared four kids; Mary Elizabeth, Dixie Lee, Phillip Crosby Jr., and Flip.

The Washington State University alum died from a heart attack on January 13, 2004. He was 69. Before his death, Phillip reprimanded his eldest brother over the claims in his autobiography.

Singer and film star Bing Crosby with his first wife, actress Dixie Lee, and their sons Gary, Lindsay. and twins Dennis and Phillip. | Source: Getty Images

Singer and film star Bing Crosby with his first wife, actress Dixie Lee, and their sons Gary, Lindsay. and twins Dennis and Phillip. | Source: Getty Images

He defended their father, explaining that Bing upheld the principles of corporal punishment but never acted out of order. In his words, per People:

"We never got an extra whack or a cuff we didn't deserve."

His twin brother, Dennis, also followed in their father's footsteps. Dennis was an occasional actor and a part of the family's band, "The Crosby Boys."

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Actress Dixie Lee, wife of singer Bing Crosby, relaxing outdoors with their twin sons Dennis and Phillip, circa 1935. | Source: Getty Images

Actress Dixie Lee, wife of singer Bing Crosby, relaxing outdoors with their twin sons Dennis and Phillip, circa 1935. | Source: Getty Images

But unlike his twin brother, Dennis had trouble keeping a marriage. Although he was married to Arleen Crosby for twenty-seven years, he experienced four failed marriages altogether and had more than three kids.

Towards the end of his life, Dennis was not close to his brothers, Gary and Phillip. They lived in the same city but never saw eye to eye. Gary maintained that their relationship was affected because of Dennis's alcohol abuse. He said:

"My problem with both Lindsay and Dennis towards the end of their lives was the fact that I was on a program – and they weren't."

Phillip Crosby, Bing Crosby, Dennis Crosby promotional photo for the ABC tv series 'The Bing Crosby Show'. | Source: Getty Images

Phillip Crosby, Bing Crosby, Dennis Crosby promotional photo for the ABC tv series 'The Bing Crosby Show'. | Source: Getty Images

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Sources confirmed that the twins hated each other passionately and rarely saw each other despite living three blocks apart. Relatives agree that Dennis and Phillip were the good and evil twins, and they spoke negatively about the latter.

Even after Dennis tragically committed suicide in 2006 at the age of 56 after struggling to deal with alcoholism, divorce, and the suicide of their youngest brother Lindsay, Phillip did not show up at the memorial service.

While Dennis never related well with his twin, he had an indestructible bond with Lindsay - his untimely death in 1989 affected him badly.

Bing Crosby pose for a picture with his three sons. | Source: Getty Images

Bing Crosby pose for a picture with his three sons. | Source: Getty Images

Following the deaths of the three brothers, family members played their roles in keeping the memories of the deceased alive. Phillip's goddaughter, Noonan, had some positive remarks about the actor.

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She explained that he was never an alcoholic but an insomniac who often reached out to her. Despite the alarming reports from his family members, Noonan maintained that Phillip was the good cop who wanted to respect his twin brother's wishes by not attending the funeral. She added:

"Phillip wouldn't have any part of one because {Dennis} just didn't want one."

Nurse Cradles Two-Month-Old Crosby Twins. | Source: Getty Images

Nurse Cradles Two-Month-Old Crosby Twins. | Source: Getty Images

LINDSAY COSBY

Lindsay was Bing's fourth son from his first marriage and the closest to Dennis. He was born on January 5, 1938. Unlike his older siblings, he had dark hair, but that was the only significant difference between him and the rest of the clan.

Lindsay worked as an actor like his family members, appearing in films like "The Glory Stompers," "Bigfoot," and "The Mechanic." He was among the "The Crosby Boys" singing group, but they broke up in 1962, following his nervous breakdown.

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But that was not the only tragedy that befell him. Lindsay had three failed marriages and fathered five children. On his third marriage Susan Marlin, he began to search for other means to make money.

Bing Crosby and his son LIndsay Crosby in 1952. | Source: Getty Images

Bing Crosby and his son LIndsay Crosby in 1952. | Source: Getty Images

His financial crisis strained the marriage between him and Marlin. Sadly, the investments set aside by his deceased mother for her sons had run dry.

Lindsay could not handle the pressure; he had been burdened with his mother's death, divorce, mental health, and drinking problems for a long time. On December 11, 1989, he took his life at his Calabasas home.

Singer and actor Bing Crosby (second left) and his sons (L-R) Lindsay, Gary, Dennis and Phillip, all wearing baseball uniforms and kneeling with baseball bats, circa 1950. | Source: Getty Images

Singer and actor Bing Crosby (second left) and his sons (L-R) Lindsay, Gary, Dennis and Phillip, all wearing baseball uniforms and kneeling with baseball bats, circa 1950. | Source: Getty Images

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HARRY COSBY

Bing had three children from his second marriage. His first was Harry Crosby, born on August 8, 1958. He also followed in his father's footsteps and became an actor. His acting credits include "Friday the 13th" and "Double Trouble."

Apart from acting, Harry earned a master's degree from Fordham University and ventured into investment banking after his dad's death. He also shares Bing's singing passion; he still makes appearances in clubs, singing and currently supports the performing arts at Lincoln Center in New York.

Harry was formerly married to Lisa, but now, he is with his second wife, Mihaela, with whom he shares two kids, Nicholas and Thea.

Bing Crosby (1901 - 1977) at his home in San Francisco with his sons Nathaniel and Harry and his daughter, Mary. | Source: Getty Images

Bing Crosby (1901 - 1977) at his home in San Francisco with his sons Nathaniel and Harry and his daughter, Mary. | Source: Getty Images

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Unlike his older siblings, Harry had a close bond with his dad. He was on an international tour with the iconic singer when he died at age 74 in Spain. The pair had performed at Brighton on October 10, 1977, before Bing began to feel unwell. Unfortunately, this was the last time father and son saw each other. Harry confessed:

"Dad and I had a really strong relationship, both professionally and personally."

American singer and actor Bing Crosby (1903-1977) with his son Harry Crosby, wearing hats and smiling as they sit on a wooden fence, 1965. | Source: Getty Images

American singer and actor Bing Crosby (1903-1977) with his son Harry Crosby, wearing hats and smiling as they sit on a wooden fence, 1965. | Source: Getty Images

MARY COSBY

Bing's only daughter, Mary, is exceptional. At age four, Mary received her Actor's Equity card. She also graduated high school at 15 and enrolled in the University of Texas, Austin, that same year. However, Mary quit college to follow her acting passion. She studied at the American Conservatory Theatre in Los Angeles.

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Mary found success in the entertainment industry. Her TV credits are "Tapeheads," "The Legend of Zorro," "The M word," and "The Seagull." 20-year-old Mary also played the legendary actress behind the character "Kristin Shepard," who shot JR in the cult-classic TV drama "Dallas."

Although, while auditioning for "Dallas," the producers were concerned that the public might not accept that Bing's daughter would fit the role description; however, it was a success and has remained her most notable role.

Nathaniel Crosby, Kathryn Crosby, Mary Crosby and Harry Crosby pose during the AMERICAN MASTERS "Bing Crosby Rediscovered" panel | Source: Getty Images

Nathaniel Crosby, Kathryn Crosby, Mary Crosby and Harry Crosby pose during the AMERICAN MASTERS "Bing Crosby Rediscovered" panel | Source: Getty Images

Bing was close to his daughter, but he was a no-nonsense father, unwilling to compromise. Before his death, he confessed that he would stop speaking to his daughter if she ever lived with a man without being married.

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But that did not stop Mary from moving in with her boyfriend, who later became her first husband— a year after Bing's demise. At the moment, Mary, whose latest feature was in 2014, lives with her husband Mark Brodka and their two sons in her Los Angeles residence.

Bing Crosby's only daughter Mary on July 23, 2014, in Beverly Hills, California. | Source: Getty Images

Bing Crosby's only daughter Mary on July 23, 2014, in Beverly Hills, California. | Source: Getty Images

NATHANIEL COSBY

The youngest of the Crosby children is Nathaniel Patrick Crosby. He was born on October 21, 1961. He was dragged into performing like his other siblings but never liked it; neither was he good for the entertainment business.

Even though he did not follow in his father's footsteps, Bing had a good relationship with Nathaniel. The singer's youngest son claimed that his dad never hit him and always spent time with his second family.

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Nathaniel claimed that Bing did not raise them to be spoiled. On the contrary, he wanted them to have value for money, so during summer breaks, they were made to do manual labor on the ranch.

 Captain Nathaniel Crosby speaks to the crowd during closing ceremonies on Day Two of The Walker Cup at Seminole Golf Club on May 09, 2021 in Juno Beach, Florida. | Source: Getty Images

Captain Nathaniel Crosby speaks to the crowd during closing ceremonies on Day Two of The Walker Cup at Seminole Golf Club on May 09, 2021 in Juno Beach, Florida. | Source: Getty Images

Despite the training process, Nathaniel yearned to be with his father. He learned golf so that he could spend time with the singer. Later, he became a golfer and won the 1981 U.S Amateur, among other competitions.

Nathaniel became father to four kids and two stepchildren from his two marriages. Although he is not a golf player, he sells luxury timeshares on the world's top golf courses.

Bing Crosby with his second family -- wife Kathryn, sons Harry and Nathaniel and daughter Mary. | Source: Getty Images

Bing Crosby with his second family -- wife Kathryn, sons Harry and Nathaniel and daughter Mary. | Source: Getty Images

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BING COSBY'S TWO WIVES

Bing was first married to the stunning actress and nightclub singer Dixie Lee. She met him when she was just 20 years old, and on September 29, 1930, the pair tied the knot. They were happily married when Lee was diagnosed with ovarian cancer and passed away in 1952.

Together the couple had four sons, Gary, twins Dennis and Phillip, and Lindsay. Lee famously inspired the 1947 film, "The Smash-Up: The Story of a Woman," based on her life. Before she passed away, their family resided at 10500 Camarillo Street in North Hollywood for over five years.

After her death, Crosby went on to date model Pat Sheehan and actresses Inger Stevens and Grace Kelly. He later fell in love with his second wife, Kathryn Grant.

Bing Crosby (1904 - 1977) with his first wife, Dixie Lee (1911 - 1952) | Source: Getty Images

Bing Crosby (1904 - 1977) with his first wife, Dixie Lee (1911 - 1952) | Source: Getty Images

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Kathryn Grant's full name was Olive Kathryn Grandstaff. The Texas-born actress graduated from the University of Texas with a Bachelor of Fine Arts in 1955 and married Crosby two years later.

She was more than thirty years his junior. They had three children, Harry, Mary, and Nathaniel, together. She mainly was retired after their marriage but made a few tv appearances, and after his death in 1977, she began accepting minor movie roles.

 Bing Crosby (1903 - 1977) with his wife, American actress and singer Kathryn Crosby | Source: Getty Images

Bing Crosby (1903 - 1977) with his wife, American actress and singer Kathryn Crosby | Source: Getty Images

On November 4, 2010, she suffered severe injuries in a car accident in Sierra Nevada. Her second husband, 85-year-old Maurice William Sullivan, was killed in the accident.

Before her demise, Grant gushed about her ex-husband's popularity. She admitted that everyone was in love with the powerhouse— which is not far from the truth. To date, Bing Cosbyis remembered as a Hollywood legend, talented singer, and great father.

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