Bing Crosby was the voice of Christmas. For decades, he was the ultimate "dad" figure in America—pipe in hand, sweater on, crooning "White Christmas" with that smooth-as-butter baritone. But if you peel back the layers of the Technicolor Hollywood dream, the reality of his domestic life was a lot more complicated than a three-minute pop song.
So, let's get the math out of the way first. Bing Crosby had seven children total. He didn't have them all at once, though. His family life was essentially a tale of two very different "acts." The first act was with his first wife, Dixie Lee, and it was famously rocky. The second act came years later with Kathryn Grant, and it looked like a totally different movie. People still argue today about which "Bing" was the real one: the strict disciplinarian of the 1930s or the mellowed-out father of the 1960s.
The First Four: The Crosby Boys and the "House of Terror"
In 1930, Bing married Dixie Lee, a rising star in her own right. Together, they had four sons. If you’ve ever seen old newsreels of the "Crosby Boys," they looked like the perfect All-American quartet. But behind the scenes? Not so much.
- Gary Crosby (1933–1995): The eldest. He’s the one who eventually blew the lid off the family secrets with his 1983 memoir, Going My Own Way.
- Dennis and Phillip Crosby (1934–1991/2004): Identical twins. Dennis’s life ended in a tragic suicide, while Phillip lived a bit longer but struggled with the weight of the family name.
- Lindsay Crosby (1938–1989): The youngest of the first batch. Like his brother Dennis, he also tragically took his own life.
Gary’s book described Bing as a father who used a leather belt for the slightest infractions. He claimed Bing would weigh his sons and, if they were over a certain limit, subject them to "thrashes." It’s heavy stuff. Honestly, when the book came out, it nearly destroyed Bing’s reputation. People couldn't reconcile the "Der Bingle" they loved with the man Gary described.
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But here’s the kicker: the other brothers didn't always agree. Phillip once called Gary a "whining brat" and defended their dad, saying the discipline was just a product of the times. It's a classic case of how two people can grow up in the same house and have completely different versions of the truth.
The Second Act: A New Start with Kathryn Grant
After Dixie Lee passed away from ovarian cancer in 1952, Bing eventually remarried Kathryn Grant in 1957. She was more than 30 years younger than him. This is where the story gets a bit surreal. It’s like Bing decided to do a "parenting do-over."
With Kathryn, Bing had three more children:
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- Harry Crosby (born 1958): He dabbled in acting (you might remember him from the original Friday the 13th) before becoming a successful investment banker.
- Mary Crosby (born 1959): The most famous of the second group. She played Kristin Shepard on Dallas—the woman who actually shot J.R. Ewing.
- Nathaniel Crosby (born 1961): He followed in his dad’s footsteps on the golf course, winning the U.S. Amateur in 1981.
This second group of kids had a vastly different experience. By the time they were born, Bing was older, wealthier, and—by all accounts—a lot more patient. He was less "belt-and-braces" and more "let's go to the golf course." Mary Crosby has often spoken about her father with nothing but warmth, describing a man who was present and loving. It makes you wonder: did he change, or was he just a different man for a different generation?
Why the Inheritance Caused a Rift
You’d think the kids of one of the richest men in the world would be set for life, right? Well, Bing was a bit "kinda" eccentric about his money. He set up blind trusts for his first four sons that they couldn't fully access until they were 65.
Think about that for a second. Sixty-five. By the time that money became available, Gary, Lindsay, and Dennis were already gone or deeply embattled. Some family historians argue this "tough love" financial move actually contributed to the depression and struggles of the older boys. They were "Crosbys" to the public, expected to live a certain lifestyle, but they didn't have the liquid cash to support it without working in their father's shadow.
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Meanwhile, the second family seemed to navigate the legacy with more ease. Whether that’s because they had a more stable upbringing or simply because the 1960s were a more "chill" time to grow up, nobody really knows for sure.
How Many Kids Did Bing Crosby Have? The Legacy Today
So, when people ask how many kids did Bing Crosby have, the answer is seven, but the story is about the divide between them. You have four sons from a era of strict, old-school parenting and three children from a more modern, televised era of celebrity.
It’s a cautionary tale about fame. Bing was a perfectionist. That perfectionism made him the biggest star in the world—the first real multimedia icon—but it also made him a difficult man to live with.
Actionable Takeaways for History Buffs:
- Read Gary Crosby’s Going My Own Way: If you want the gritty, unfiltered side of the story, this is the source. Just remember to balance it with Phillip Crosby’s rebuttals.
- Watch the 1970s Christmas Specials: You can see "Late-Era Bing" interacting with Harry, Mary, and Nathaniel. It’s a fascinating look at his second chance at fatherhood.
- Check out Denise Crosby: If the name sounds familiar, she’s Bing’s granddaughter (Dennis's daughter) and played Tasha Yar on Star Trek: The Next Generation. The talent definitely stayed in the bloodline.
Ultimately, Bing Crosby’s family tree is a mix of immense talent and deep tragedy. He wasn't just a voice on the radio; he was a man who struggled to balance the demands of being a global icon with the messy, human reality of raising seven very different individuals.