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.

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0:00 - Introduction
0:44 - The Macron’s Love Shove
2:16 - Interview Begins
2:45 - Favorite night with Sinatra
4:57 - Growing up in Chicago
5:42 - Breaking into Comedy
6:44 - The Show Shine Incident
10:05 - Tim Reid
15:56 - Why Tom’s Act Worked
18:39 - Why did Tim & Tom break up?
22:10 - Playing the Tonight Show
26:00 - Sammy Davis Jr.
29:19 - Smokey Robinson
30:31 - Jack Benny
32:27 - Writing a Comedy Set
33:36 - Robin Williams
34:40 - The Power of Comedy
36:40 - What’s missing in Today’s Comedy
39:41 - Frank Sinatra
44:09 - Church with Frank
46:51 - Frank’s Goodbyes
50:58 - Did Frank Warm Up Before Shows
52:06 - Sinatra and his Tux
55:48 - Uncle Frank
1:01:04 - The Night Sinatra Fell
1:03:51 - What did Sinatra Teach You
1:14:01 - The Sound of Laughter
1:15:51 - Arroyo Grande Questionnaire