Comedian Tom Dreesen spent 14 years opening for Frank Sinatra, traveling the world with the Chairman of the Board, and sharing moments few ever witnessed. But beyond the glitz of Las Vegas stages and sold-out arenas, it was what Sinatra shared off stage that left the deepest impression.

In this candid interview, Dreesen reveals what Frank Sinatra taught him about showbiz at the highest level, the role of faith in both of their lives, and the meaning of real friendship — forged in midnight conversations, private Masses, and unspoken loyalty.

From emotional backstage memories to laugh-out-loud stories about Sammy Davis Jr., Smokey Robinson, and even a surprise moment with Robin Williams, this episode of Arroyo Grande is a heartfelt tribute to an era of class, grit, and genuine connection.

If you’ve ever wondered what it was like to really know Sinatra — this is the conversation you’ve been waiting for.

🔔 Subscribe for more inspiring conversations: Arroyo Grande, available on YouTube, Apple Podcasts, iHeart, and everywhere you listen, watch & stream.

Comedian Tom Dreesen spent 14 years opening for Frank Sinatra, traveling the world with the Chairman of the Board, and sharing moments few ever witnessed. But beyond the glitz of Las Vegas stages and sold-out arenas, it was what Sinatra shared off stage that left the deepest impression.
In this candid interview, Dreesen reveals what Frank Sinatra taught him about showbiz at the highest level, the role of faith in both of their lives, and the meaning of real friendship &mdash; forged in midnight conversations, private Masses, and unspoken loyalty.
From emotional backstage memories to laugh-out-loud stories about Sammy Davis Jr., Smokey Robinson, and even a surprise moment with Robin Williams, this episode of Arroyo Grande is a heartfelt tribute to an era of class, grit, and genuine connection.
If you&rsquo;ve ever wondered what it was like to really know Sinatra &mdash; this is the conversation you&rsquo;ve been waiting for.
🔔 Subscribe for more inspiring conversations: Arroyo Grande, available on YouTube, Apple Podcasts, iHeart, and everywhere you listen, watch &amp; stream.

Raymond Arroyo, host of Arroyo Grande navigates and analyzes the culture with insight, satire, and style.  The New York Times Best Selling author, award-winning producer, chart topping vocalist and broadcaster wades deep into the manners, lifestyle trends, people, faith, and art of the moment-- celebrating the best, while lampooning the rest.  During his surprising conversations with celebrities, thought leaders and culture-makers, you’ll discover life lessons, practical advice, and inspiring examples to live by. This fun, entertaining and unifying show helps listeners transform their lives into a broad, thriving Arroyo Grande.  Each episode bursts its banks- and wait until you hear “How It Ends…”

Raymond Arroyo, host of Arroyo Grande navigates and analyzes the culture with insight, satire, and style.&nbsp; The New York Times Best Selling author, award-winning producer, chart topping vocalist and broadcaster wades deep into the manners, lifestyle trends, people, faith, and art of the moment-- celebrating the best, while lampooning the rest.&nbsp; During his surprising conversations with celebrities, thought leaders and culture-makers, you&rsquo;ll discover life lessons, practical advice, and inspiring examples to live by. This fun, entertaining and unifying show helps listeners transform their lives into a broad, thriving Arroyo Grande.&nbsp; Each episode bursts its banks- and wait until you hear &ldquo;How It Ends&hellip;&rdquo;

Arroyo Grande with Raymond Arroyo

Tom Dreesen: What Frank Sinatra Taught Me About Life, Faith… and Real Friendship

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/311ab425-0bd1-4786-87d6-b2eb0069d805/transcript