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From Chart-Toppers to Chart Stoppers? 17 Music Legends’ Wild "Then and Now" Transformations That Will Blow Your Mind!

Added on October 19, 2025 inCelebrity News Cards, Entertainment News Cards

Remember when these artists were basically the soundtrack to our lives (and, yes, our glorified MySpace playlists) two decades ago? Fast-forward 20 years, and their journeys have taken some twists and turns that might just make you raise an eyebrow—or laugh out loud. Maybe it’s the influence of today’s Leo sun, encouraging bold transformations and spotlight steppin’, that’s made these stars reinvent themselves in the most unexpected ways. From chart-topping hits to entirely new adventures, their stories remind us: time changes everything—even the biggest music giants. So, want to see who’s still rocking the stage and who’s taken a detour through the wild side? Let’s dive in. LEARN MORE.

Then Vs Now: 17 Artists Who Ruled Music 20 Years Ago

These artists absolutely dominated the airwaves (and our MySpace accounts) 20 years ago, and since then, time has taken them in some interesting directions. Let’s check in:

3.

Outkast

6.

Gym Class Heroes

7.

Damien Rice

9.

My Chemical Romance

10.

Sean Kingston

11.

Limp Bizkit

12.

Ben Lee

13.

Death Cab for Cutie

14.

Vitamin C

15.

Fall Out Boy

17.

Clay Aiken

Which other artists from 20-plus years ago are you curious about? Share them in the comments!

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