Bing Crosby has maintained a legacy not only through his illustrious music career but also with his seven children.
One of the most successful music acts of the 20th century, Bing was widely known for his Christmas specials and his acting career, during which he won the Best Actor Oscar for the 1944 classic Going My Way. Throughout his life, Bing married twice and welcomed seven children who went on to continue their dad’s legacy through music, acting and even sports.
The singer was married to his first wife, actress and singer Dixie Lee, from 1930 until her death in 1952 from ovarian cancer. The pair welcomed four sons together: Gary, twins Dennis and Phillip, and Lindsay, who are all deceased. Music bonded the brothers and their father together as they all performed on his radio shows and even recorded a song together in 1950 titled “A Crosby Christmas Medley.”
Bing then met actress Kathryn Grant while doing interviews for her column on the set of his 1954 film White Christmas. The couple married in 1957 and were together for 20 years before the singer’s death in 1977 at age 74 from a heart attack. Throughout their time together, Bing and Kathryn welcomed three children: Harry Lillis III, Mary and Nathaniel. Kathryn died of natural causes in September 2024. She was 90 years old.
While Bing’s youngest three have recalled fond memories of their dad, his oldest four sons shared more complicated feelings about their father.
“The idea was to be ordinary,” Gary wrote in his 1983 memoir Going My Own Way. “There were a few problems with being just an ordinary kid. For one thing, Dad didn’t seem to be just an ordinary father.”
Here’s everything to know about Bing Crosby’s seven children: Gary, Dennis, Phillip, Lindsay, Harry Lillis III, Mary and Nathaniel.
Gary Crosby
Bing and Dixie welcomed their first child, Gary, on June 27, 1933.
He followed in his dad’s footsteps and pursued a career in music alongside his brothers Dennis, Phillip and Lindsay as part of the singing group The Crosby Boys. The foursome performed on their dad’s radio shows and released music throughout the 1950s and ‘60s. The others continued as a trio after Gary departed from the group in 1959.
The eldest Crosby son also duetted with his father on “Sam’s Song” and “Play a Simple Melody” which became the first double-sided gold record in history.
Gary went on to pursue a career in acting and starred in numerous TV shows including Adam-12, The Bill Dana Show and Hunter. He also made guest appearances on popular shows like The Twilight Zone, Matlock and Murder, She Wrote. On film, Gary largely played supporting roles throughout the 1950s and early ‘60s and appeared alongside the likes of Pat Boone and Frankie Vaughan in films including Mardi Gras and The Right Approach.
In 1983, six years after his father’s death, Gary released an autobiography titled Going My Own Way in which he accused his dad of abusing him and his brothers. The memoir went into detail on the alleged emotional and physical abuse Gary experienced and was met with mixed reactions from the Crosby family.
His brother Dennis described the book as “Gary’s business” in a 1983 interview with PEOPLE, while Lindsay said that he hoped the memoir “clears up a lot of the old lies and rumors.”
Bing’s brother, Bob Crosby, came to the crooner’s defense after the autobiography was released, saying that Bing was a “disciplinarian,” as their mother and father had been, and reiterated that he and Bing were also “brought up that way.”
In his personal life, Gary had three marriages and welcomed a son, Steven, with his first wife Barbara Cosentino. He later became a lecturer for Alcoholics Anonymous after his own journey with alcoholism. Gary died of lung cancer in 1995. He was 62.
Dennis Crosby
Bing and Dixie welcomed their second and third sons, twins Dennis and Phillip, on July 13, 1934.
Like his older brother Gary, Dennis performed as part of The Crosby Boys but didn’t pursue a career in music following the group’s disbandment. “I guess I wasn’t cut out to be an entertainer,” Dennis once said, per his 1991 obituary in The Washington Post. “I was always painfully self-conscious out there in the spotlight with my brothers.”
Outside of his complicated relationship with music, Dennis briefly pursued a career in acting, appearing as himself in films like Duffy’s Tavern and Out of this World, and playing roles in later films and TV shows like Sergeants 3 and Ben Casey.
In 1958, Dennis married showgirl and model Pat Sheehan, whom his father had also briefly dated. The pair welcomed two sons together, Dennis Michael Jr. and Patrick Anthony, and Dennis adopted Sheehan’s son from a previous marriage, Gregory. Following his divorce from Sheehan, Dennis married Arleen Newman and the couple welcomed two daughters, Erin Colleen and Kelly Lee. As in his first marriage, Dennis also adopted Newman’s daughter from a previous relationship, Catherine.
Dennis also welcomed daughter Denise, during a relationship with Marilyn Miller Scott, who rose to prominence for her portrayal of Tasha Yar in Star Trek.
In 1991, Dennis was found dead from a gunshot wound that authorities said appeared to have been self-inflicted. Dennis’ death was treated as a suicide. He was 56.
Phillip Crosby
Bing and Dixie welcomed their son Phillip on July 13, 1934.
After performing as part of The Crosby Brothers, Phillip went on to launch his own solo act performing on The Ed Sullivan Show and appearing alongside Bob Hope for several acts including The Bob Hope Christmas Special. Similar to his twin and older brother, Phillip also briefly pursued acting, appearing in films in the 1960s like Robin and the 7 Hoods and None but the Brave.
In his personal life, Phillip was married four times and welcomed several children, including daughter Dixie Lee and son Brian from his first marriage to Sandra Jo Drummond, and daughter Mary Elizabeth and son Flip from his second marriage to Mary Joyce Gabbard. Philip also welcomed a son, Philip Jr., with his fourth wife, Peggy Compton.
Following the release of Gary’s autobiography, in which he alleged that his dad abused him and his siblings, Phillip disputed the claims, causing friction between him and his brother. “We never got an extra whack or a cuff we didn’t deserve,” Philip told PEOPLE in 1983.
The actor also said that he believed his parents had a “very good marriage,” and that he “understood Dad probably better than anybody in the whole family.”
Like his elder brother, Phillip was vocal about his struggles with alcoholism throughout his life. In 2004, Philip was found dead of natural causes. He was 69.
Lindsay Crosby
Bing and Dixie’s youngest son, Lindsay, was born on Jan. 5, 1938.
Like his brothers, Lindsay pursued a career in music in the 1950s performing as part of The Crosby Brothers and sometimes individually on his dad’s radio show. As a teenager, Lindsay made two solo records with John Scott Trotter and his orchestra for record label Decca titled “That’s What I Want for Christmas” and “Dear Mister Santa Claus.” When The Crosby Brothers disbanded, Lindsay went to work reading scripts for his dad.
As he grew older, Lindsay also dabbled in acting, appearing in films in the 1960s and early ‘70s like The Mechanic, Bigfoot and The Glory Stompers. Throughout his life, Lindsay married three times to Barbara Diane Fredrickson, Janet Sue Schwartze and Suzy Crosby. He had four sons.
Unlike his brothers Phillip and Dennis, Lindsay voiced support for his older brother Gary when his autobiography was published. “I’m glad he did it,” Lindsay told PEOPLE in 1983. “It was something Gary had to do.” Although he recognized that Bing could be tough, Lindsay told PEOPLE, “Dad would say, ‘Goodnight, I love you,’ and that to me was heaven.”
“I still miss him,” Lindsay added at the time. “I probably didn’t realize how much I’d miss him when he died.” The singer went on to say that he chose to remember “all the good things I did with my dad and forget the times that were rough.”
Like his siblings, Lindsay struggled with alcoholism throughout his life. He died in 1989 in a suspected suicide and was found by authorities in his Calabasas home. He was 51 years old.
Harry Lillis Crosby III, 66
Bing and Kathryn Grant’s first child together, Harry Lillis III, was born on Aug. 8, 1958.
In his early life, Harry appeared on Christmas specials with his father and recalled what the experience was like in the 2014 documentary Bing Crosby Rediscovered. “I went down to watch him do the Hollywood Palace at age 6, and they asked me if I knew any songs,” Harry shared.
“And I said, well, I just learned a Christmas carol. So, of course, that fit well and ended up doing the show with them—complete black tie and shorts and shiny black shoes,” he continued. “And that was the beginning of the Christmas shows.”
Despite the bright lights in his childhood, Harry recalled, “You know we were raised kind of as normal kids, we thought so, in San Francisco. And you know, we loved him as a dad.”
In his later career, Harry pursued acting and was widely known for playing Bill in the 1980s film Friday the 13th. He also had roles in TV shows like Double Trouble.
Harry now works in business as an investment banker. He began his career at Lehman Brothers and went on to assume partner roles at Cranemere and Snow Phipps. In 2019, he joined Trilantic North America as a partner of business development.
Harry received a master’s degree from the London Academy of Music and Dramatic Art and a business degree from Fordham University.
In Bing Crosby Rediscovered, Harry reflected on his upbringing and how his mother made sure the kids realized they were “kind of in a public light.”
“He was an integral part of our family as first as the father. You know, I loved what he loved about music and the fact that he imparted that on us but in a very casual way,” Harry shared. “He was a very low key guy and part of the reason I think we were in San Francisco as a family is because he wanted to kind of stay low key.”
Harry continued, “He engaged when he had work, and we recognize that we were all kind of in a public light. My mother instilled that in us, you know, early on. So we would try and stay out of trouble for the most part.”
The businessman married Dr. Mihaela Skobe in 2003 and the pair share at least two children. Bing’s grandkids even keep up a tradition in honor of their grandfather. Each Christmas, Harry told The Express, “My son, Nicholas, and daughter, Thea, sing and play “White Christmas” on the piano for everyone.”
Mary Crosby, 65
Bing’s only daughter, Mary Crosby, was welcomed by the singer and his wife, Kathryn, on Sept. 14, 1959.
Although she appeared in her dad’s Christmas specials, unlike her siblings, Mary never pursued a career in music and instead worked as an actress. She is widely known for playing Kristin Shepard on the hit soap opera Dallas from 1979 to 1981.
Mary’s extensive TV résumé also includes roles in popular shows like Starsky & Hutch, Beverly Hills, 90210, Murder, She Wrote and Star Trek: Deep Space Nine.
The actress also had a slew of roles on film, appearing in the 2005 flick The Legend of Zorro alongside Antonio Banderas and Catherine Zeta-Jones. Her last film was Henry Jaglom’s 2014 comedy/drama The M Word starring Michael Imperioli, Corey Feldman and Tanna Fredrick.
Mary was married to Eb Lottimer from 1978 to 1989 — she then tied the knot with Mark Brodka in 1998. The pair have welcomed at least two children together.
Nathaniel Crosby, 63
Bing and Kathryn welcomed his youngest son, Nathaniel, on Oct. 29, 1961.
Rather than continuing his dad’s legacy through music, Nathaniel picked up another one of Bing’s passions: golf. On his website, the golfer shared that Bing was “determined” that Nathaniel and his siblings “didn’t grow up to be Hollywood brats.” Part of this goal included Nathaniel learning how to play golf to “spend more time” with his father.
At age 15, Nathaniel won the championship at his family’s country club, Burlingame Country Club, and his father told him, “Today is the happiest day of my life.”
Nathaniel went on to become the U.S. Junior Medalist in golf in 1979, and won the U.S. Amateur Championship in 1981. He also played on the European Tour from 1985 to 1987, and competed in three Masters, the U.S. Open, two British Opens and was on the winning teams for the World Amateur and Walker Cup.
After retiring as a touring professional, Nathaniel has continued to work as a golf industry executive and is the founder and president of AppleTree Management Group which, per his LinkedIn page, coordinates “private golf clubs into an ultra-affluent golf membership program.”
In 2016, Nathaniel co-authored a memoir with John Strege titled 18 Holes with Bing: Golf, Life, and Lessons from Dad in which he shared anecdotes and memories from spending time on the golf course with his father.
As of 2016, Nathaniel and his wife Sheila shared six children: four from his first marriage and two from hers.
If you or someone you know is considering suicide, please contact the 988 Suicide and Crisis Lifeline by dialing 988, text “STRENGTH” to the Crisis Text Line at 741741 or go to 988lifeline.org.
Source: People
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