Bing Crosby was the voice of a generation. When you hear "White Christmas," you aren't just hearing a song; you're hearing the soundtrack of 20th-century Americana. But away from the velvet microphone and the "Der Bingle" persona, the man had a massive, complicated family life that basically split into two different eras.
So, let's get right to it. How many children did Bing Crosby have? Bing Crosby had seven children in total. He fathered four sons with his first wife, Dixie Lee, and then had two more sons and a daughter with his second wife, Kathryn Grant.
Honestly, the way these two families grew up couldn't have been more different. It's almost like Bing lived two entirely separate lives as a father. While the first four boys grew up in the shadow of their father’s skyrocketing fame and strict discipline, the younger three experienced a much mellower, older version of the star.
The First Family: Four Sons and a Lot of Friction
Bing married Dixie Lee, a singer and actress, back in 1930. They were the "it" couple of the era. Together, they had four sons who were born in quick succession during the height of the Great Depression and the start of World War II.
- Gary Crosby (1933–1995): The eldest. Gary was the one who eventually blew the lid off the family's private life with his 1983 memoir, Going My Own Way.
- Dennis Crosby (1934–1991): One half of the Crosby twins.
- Phillip Crosby (1934–2004): The other twin. Unlike Gary, Phillip often defended his father, though he didn't deny that things were "tough" at home.
- Lindsay Crosby (1938–1989): The youngest of the first batch.
These four boys actually tried to follow in their dad's footsteps. They formed a harmony group called The Crosby Boys in the late 1950s. They played the big Vegas rooms and did TV spots, but they never quite escaped the "son of Bing" label.
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Tragically, the lives of the first four sons were marred by struggles with alcoholism and depression. Lindsay and Dennis both died by suicide, and Gary’s book painted a picture of a father who was emotionally distant and physically punishing. Bing was a product of his time—he believed in "spare the rod, spoil the child," but by modern standards, it was a rough upbringing.
The Second Family: A New Start with Kathryn Grant
After Dixie Lee passed away in 1952, Bing eventually remarried. In 1957, he wed Kathryn Grant, an actress who was thirty years his junior. This second marriage brought three more children into the world, and by all accounts, Bing was a changed man.
- Harry Crosby (Born 1958): He did a bit of acting (you might remember him from the original Friday the 13th) but eventually left Hollywood for a successful career in investment banking.
- Mary Crosby (Born 1959): The only daughter. She’s famous in her own right for playing Kristin Shepard on Dallas—the woman who actually shot J.R. Ewing.
- Nathaniel Crosby (Born 1961): The youngest. He became a high-level amateur golfer, winning the 1981 U.S. Amateur, which probably made his golf-obsessed father incredibly proud.
By the time these three were growing up, Bing was in his 60s and 70s. He was semi-retired and much more present. Mary has often spoken about how "warm and funny" her dad was, which stands in stark contrast to the "Captain Bligh" persona Gary described in his book. It’s a classic case of a man learning from his past mistakes, though that was little comfort to his older sons.
The inheritance "twist" that people still talk about
One of the most interesting (and kinda harsh) things about Bing’s relationship with his children was his will.
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Bing didn't just hand over the keys to the kingdom. He set up a spendthrift trust for his first four sons. They couldn't access the bulk of their inheritance until they were 65 years old.
Think about that for a second.
Bing wanted them to earn their own way and feared that handing them millions would only fuel their existing struggles with alcohol. Ironically, only Phillip lived long enough to actually see that money. Gary, Dennis, and Lindsay all passed away before they hit the age of 65.
What we can learn from the Crosby legacy
When you look at the question of how many children Bing Crosby had, you’re looking at a tale of two very different Hollywood experiences.
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If you're researching the Crosby family, don't just stop at the names. The real depth is in the nuance of how the culture of parenting shifted between the 1930s and the 1960s. Bing went from a strict, touring superstar to a doting, older father.
Takeaways for fans and researchers:
- Check the sources: If you're reading about the "abusive" Bing, you're likely reading Gary Crosby's perspective. If you're reading about the "saintly" Bing, you're reading Mary or Nathaniel's. The truth is probably somewhere in the middle.
- The Talent was Real: All seven children were gifted. Whether it was music, acting, or sports, the "Crosby Gene" was powerful.
- Legacy Matters: Despite the family drama, the Crosby name remains synonymous with a specific era of class and talent.
If you want to understand the man behind the voice, start by watching his 1954 film The Country Girl. He plays an alcoholic actor, and many critics believe it’s the most honest he ever was on screen—partially because he was drawing from the very real struggles he saw in his own home.