What the Chauffeur Knew: The Hidden Story of Rudy Vallée

From one descendant to the next, nobody expects the unexpected in their family tree. Grandma ran the local switchboard. Aunt Bonnie made the best pies! Cousin Jim was a respected mechanic. Great-grandpa worked at the old mill. Well, what if you found out that your great-grandpa was the personal driver for Rudy Vallée. That was the discovery and legend for the family of Silvana de la Osa.

Silvana came across this fact repeated by her family over the years, but it wasn’t until she inherited her great-grandfather’s personal writings that the bigger picture unfolded and a world of mystery behind America’s First Pop Star became a years-long hunt for answers.

In a podcast series entitled, The Rudy Vallee Files: Secrets of America’s First Pop Star being premiered on Substack, Ms. de la Osa is shining a light on what her grandfather knew and couldn’t tell about Mr. Megaphone’s rather dastardly alter-ego.

In Sylvana’s own words:

Ralph de la Osa Sr. was my great-grandfather, and, yes, he was the chauffeur to Rudy Vallée (1931-37 in NYC), and something that he called Rudy’s “aide de camp”. Over the course of the early episodes, I will share with the audience the story as my great-grandfather told it regarding how Rudy and his lawyer ruined Fay Webb Vallée (Rudy’s second wife’s) reputation.

In later episodes, I dive a little deeper into what Gramps (as I call him for a shorter moniker) didn’t include and why that might be the case. I will also share what I discovered when I started researching Rudy and his lawyer. There will be discussions of direct connections to mobsters, manipulation of the press, and speculation regarding deaths that happened around Vallée.

What sets Vallée apart from most stars is that he was the very first one. He opened the door for Sinatra and Crosby. He made the careers of many people. He’s a more influential figure to the American psyche and the infrastructure of the entertainment industry than we give him credit for. Bill Clinton played his saxophone on TV. Ronald Reagan and Richard Nixon called him their friend. All of the most powerful and the most corrupt people in New York City in the early 1930s loved him and wanted to leverage Rudy for themselves or be his friend.

I have always been interested in the music of the times, with my favorites being primarily Billie Holiday and Ella Fitzgerald. Learning more about Rudy the way that I have, has not endeared me to him. I do enjoy some of the songs he plays, but it does help to know he will no longer benefit financially from my listening to them.

My immediate grandfather, Ralph Jr, was a piano player and even played on the radio for a bit as a child. He was always musically inclined and shared a lot of the music from the era.* (*Ralph Jr. and his sister Dorothy were taught piano by their father Ralph Sr., who had his own musical inclination, on a cardboard keyboard cutout, which is all the family could afford, later earning their own regional claim to fame on radio in the ’30s and ’40s as duo pianists on stations in NY such as WJZ, WMCA and even on CBS’ Major Bowes Amateur Hour)

What this project has done is bring me a lot closer to my family, including distant family I didn’t know before I started this research. I’ve learned so much about my great-grandfather as well and what his life experience was like, which has helped me better understand my grandfather and mother too. Empathy grows through understanding.

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Perhaps more scandalous than Vallée’s outs with the paparazzi and press during his years of fame, we get the opportunity now in the 21st century to hear the inner workings of this once beloved bandleader and crooner from the words of the literal man “behind the wheel,” all thanks to a great-grandaughter with a super sleuth’s knack. Don’t miss this!

Silvana’s podcast can be found on her Substack page: whatsurfaced.substack.com, and Ralph de la Osa’s now-published manuscript, The Secrets My Great-Grandfather Tried to Tell: The Hidden Story of Rudy Vallée as Told by His Chauffeur, is available through amazon.com.