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Phil Crosby, jazz singer and grandson of Bing Crosby, talks about his legendary grandfather, the Bing Crosby and Bob Hope “Road” movies, growing up around Dean Martin and the influence of his stepdad, Jack Klugman. From his start in the LA music scene to life as a jazz singer, Phil has a rich story to tell.
On this episode of Relatively Famous, I get the chance to have a great conversation with Bing Crosby’s grandson, Phil Crosby Jr.
Phil’s father was one of the four boys from Bing Crosby and Dixie Lee’s marriage. And as Phil puts it, “I’m sort of from the black sheep side of the family.”
His grandfather, of course, was the legendary Bing Crosby, a singer and actor who won the Oscar for Best Actor Oscar in Going My Way (1944). Bing had an incredible musical career with 396 chart singles and 41 number one hits. But for a lot of us, he’ll always be associated with White Christmas, both the song and the movie (1942). It’s a family tradition in our house to watch it every year around the Christmas holidays.
I suggest everyone take a few minutes to Google Bing Crosby. He really did leave a huge mark on entertainment history.
Phil and I talk a little about his grandfather and how those famous Bing Crosby and Bob Hope “Road” movies came about after an on-stage improv session at a charity event. Phil describes the Bob & Bing as “frenemies,” which I thought was a great way to put it.
We also get into Phil’s own journey through music. He talks about trying to break into the LA rock scene, eventually leaving that Hollywood music lifestyle behind, and traveling around the country trying to figure out who he was and what he really wanted to do. That journey ultimately led him to jazz, where he found his path.
You might think being Bing Crosby’s grandson would give you a pretty easy ride in the entertainment business. And while a famous last name can certainly open a few doors, it also comes with a lot of expectations and comparisons. Sometimes you have to work even harder to prove yourself as your own person and not just somebody’s grandson.
Phil put in the time, did the work, and developed his own style. Today, he’s a respected and successful world-class jazz singer, making his own mark in the music world.
Phil once performed with my friend Ricci Martin, Dean Martin’s son, and Louis Prima’s son Louis Prima Jr. with hopes of expanding the show. If you follow this podcast, you know I love these family connections, we had Louis Prima’s daughter, Lena Prima on in Season 2 Episode 47.
Now, White Christmas is certainly a classic, but the Bing Crosby and David Bowie duet of “Peace on Earth / Little Drummer Boy” has always fascinated me. I think it’s beautiful. So naturally, I had to ask Phil who he would love to do a duet with.
Corey Feldman was not the answer I was expecting. And neither was the reason why! You’ll have to listen to that part of the conversation for yourself.
With White Christmas being such a big part of the Crosby legacy, we discussed his Christmas at home and what the holidays were like with the Crosbys. Let’s just say that Godzilla and Star Wars hold some pretty deep memories for Phil!
Phil gives us the lowdown on what it’s really like being a professional jazz singer, performing in jazz clubs and venues around the world, and how life on the road as a jazz musician compares to life as a rock star.
We also talk about his life as a dad, his mom dating Dean Martin, who always called him “The Kid,” and the influence his stepfather, Jack Klugman, had on his life. We ended with a really touching conversation about Jack, the love he showed Phil’s mom, and the impact he had on both of them.
There are so many interesting stories in this conversation, from growing up connected to Hollywood royalty to finding your own identity and building a career on your own terms.
I hope you enjoy spending some time with Phil as much as I did. And if he’s performing in your area, go get yourself some tickets! Tell him you heard his episode here on Relatively Famous.
Phil Crosby Jr. https://philcrosbyjr.com/ https://www.instagram.com/crosbycrooner/ https://www.facebook.com/PhilCrosbyJr https://www.tiktok.com/@philcrosbyjr
Crosby/Hope “Road” movies: https://www.imdb.com/list/ls063633377/
Website: https://www.relativelyfamous.net/