Usher, baby.
It’s time for Mike and me to do an episode on Usher Raymond, who we’ve both been rocking with for a very long time.
Confessions is one of the biggest albums of the 2000s. We use Confessions as the lens to discuss Usher.
Here are some of the things we discuss and cover:
From a nine-year-old in a Chattanooga church choir to a Star Search discovery to a 15-year-old whose debut album nearly got him dropped.
How Puffy personally reshaped Usher into one of the only artists with No. 1 hits in three consecutive decades.
Building My Way, then surviving the Napster leak that forced a total rebuild of 8701.
How the public collapse of Usher’s relationship with TLC’s Chilli became the emotional fuel behind Confessions.
The real stories behind “Yeah!” (a beat almost lost to Petey Pablo days before Usher could use it), “Burn,” and “My Boo” (which Usher reportedly hated at first, and which was almost recorded with Beyoncé instead of Alicia Keys).
Why co-writer Jermaine Dupri says the song isn’t actually about Usher’s life at all.
Ranking Usher’s full discography.
Grammy Redux: Eight wins — and the Album of the Year trophy that’s somehow still missing.
Dream Collaborator: Michael Jackson, plus the real T-Pain session that fell apart over a leaked reference track.
Listen above or find us everywhere else below.
🌐 Website: 50for50.net
🎙️ Apple Podcasts: 50 For 50: Life, Music, Friendship
🎧 Spotify: 50 For 50
📺 YouTube: @50_For_50
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✍️ GG’s Substack: The Cool Check-In











