Wingmen Show

About Wingmen Show

Two Dope Boys in a Navy jet. The Wingmen Show is a weekly podcast about challenges and opportunities in everyday life. Your hosts are two guys born in Harlem, New York previously unknown to each other. Separately, they became Navy pilots flying high performance jet aircraft on and off of aircraft carriers patrolling the world’s oceans. Their paths did not cross formally until they ended up flying for the same airline after their active-duty military service had ended. They have a wide range of experiences spanning the worlds of basketball and boxing. Drew’s father is Drew Bundini Brown, Muhammad Ali’s Wingman and coined the iconic phrase “Float Like A Butterfly Sting, Like A Bee". Martial Arts and Show Business are also areas of mutual interest. Drew has been featured nationally on television programs such as the Donahue Show and the Today Show. He has also appeared in hundreds of newspapers and magazines. Both are published authors as well as former Navy jet pilots and Commercial Airline Pilots; they retired after having flown the Boeing 777 airliner. The cultural mix of religions, immigrant parents and grandparents from Europe and the Caribbean gives them an uncommon perspective on racial matters. Melding the cultures of New York City, Pittsburgh, New Orleans, Memphis, the Caribbean and Atlanta has helped shape their worldview when combined with the life they have seen and experienced having flown extensively to countries throughout the world.They are wingmen to each other, providing advice, guidance and constructive criticism when needed. The goal of the show is to inspire and entertain those unafraid to expand their minds and perhaps learn something new in the hope that the listeners can become wingmen to others. Each one, teach one.

Publisher

Drew Brown and Paul Thompson

Category

education · news · society & culture

Language

en

Explicit

No

First episode

19 Apr 2021

Latest episode

3 Nov 2026

Latest episodes

250 episodes in the feed.

1. 

   3 Nov 2026

   Teach Them the Gouge--Pass On the Inside Information

   Sent us text! We would love to hear from you! You fought your way through the door. Now what? In Episode 268, Commander Drew Brown and Dr. Paul Thompson ask a question every person who has made it should answer: Are you holding the door open or telling the next person to fight just as hard? Drawing on their experience as Black naval aviators, the Wingmen make the case that passing on the gouge isn’t lowering the standard. It’s knowing where to put the work. Explain the process, make the intro...

2. 

   27 Oct 2026

   When Nobody Answers: Follow Up—or Move On

   Sent us text! We would love to hear from you! You sent the application. You made the call. You wrote the proposal. And then—nothing. In Episode 267, Commander Drew and Dr. Paul take on one of the most frustrating spots in any career or life: the silent inbox. When do you keep knocking, and when do you take your energy somewhere it will be put to use? Drawing on their years as Black aviators in the Navy, the Wingmen make the case for keeping the mission while being willing to change the ...

3. 

   13 Oct 2026

   What the Hell Is Life All About?

   Sent us text! We would love to hear from you! Every now and then you have to stop chasing the next thing long enough to ask the big question: what is life really all about? In Episode 265, Commander Drew and Dr. Paul turn to Japan for some strong gouge—five time-tested philosophies that offer practical ways to live with more purpose, gratitude, and peace. From ikigai (your reason for getting up in the morning) to wabi-sabi (finding beauty in a few dents in the fuselage), the Wingmen mak...

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

169,865

Score snapshot 15 Sept 2025

Apple Podcasts (US)

5.0 / 5

11 ratings

Podcast Authority Score: 72 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

80

Social presence

0

YouTube

82

Engagement

77

Contact Wingmen Show

Guest appearances

Does not typically book guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

Questions about Wingmen Show