Skip to content

Macy Gray

October 28, 2026 · 59 min

Show notes

On this week’s episode of Artist Friendly, Joel Madden sits down with Macy Gray.


Born in Canton, Ohio, Gray took her stage name from a family friend who used to shoot pool at the house. She headed west to study at USC, then was dropped by her first label before her debut could come out and moved back home to pursue teaching. In 1999 she released On How Life Is, a multi-platinum debut that produced “I Try,” the song that won her the Grammy for Best Female Pop Vocal Performance in 2001. Since then, she’s sold more than 25 million records across ten studio albums and has been inducted into the National Rhythm & Blues Hall of Fame in her hometown. Now she’s gearing up for a new album, The Trouble with the Truth, and a tour to match.


In conversation with Joel, Macy digs into what AI and streaming mean for working artists, what “Redemption Song” taught her about freedom on stage, growing up in a Canton steel-town family, and why her parents never saw a music career coming.


(0:00) – When Music Careers Were a New Idea
(1:04) – What 'Redemption Song' Means to Macy
(7:50) – Staying Sensitive in a Busy City
(10:18) – How the Music Industry Has Changed
(12:22) – Making Sense of an AI Future
(31:44) – Canton Roots and Midnight Radio
(40:42) – A Voice Like No Other
(47:01) – Acting, Streaming, and Album Plans

Learn more about your ad choices. Visit megaphone.fm/adchoices

All episodes of Artist Friendly with Joel Madden

Settings

Display

Language

Decides which stations you see first on the home page.

History

Recently played stations and episodes and your latest searches are only stored in this browser.

Notifications

A short notice when a podcast you follow has a new episode. Turn off single podcasts with the bell on their page.

Account

Save favorites – in the app and on the website.

Keyboard shortcuts

/
Open search
Space
Play or pause
← →
In the player: back 15 s, forward 30 s (episodes) · in a row: next tile
↑ ↓
In a row: target within the tile
Home / End
In a row: first or last tile
Esc
Close window or menu
?
This overview
Now playing

Go to station page

Play next

    Add episodes with “Play next” – they play after the current episode.