That Was Then & This Is Now: Taylor Swift

How much can an artist change in nearly two decades? A LOT.

Welcome to That Was Then & This Is Now, a brand-new Hits 96 feature where we take some of our core artists you hear all the time and put their THEN and NOW side-by-side.

And for our very first edition, we’re starting with one of the biggest artists in music history: Taylor Swift.

Back in 2008, Taylor was just 19 years old and introducing the world to the Fearless era. One of the songs that helped turn her into a household name was “Love Story,” a romantic, country-pop take on Romeo and Juliet that became one of the defining songs of her early career. The iconic music video even gave us Taylor in full period-piece mode.

Fast-forward to 2026, and Taylor is still finding new ways to make music part of the biggest moments in pop culture. Her latest song, “I Knew It, I Knew You,” appears on the Toy Story 5 soundtrack and gives us a very different snapshot of where Taylor is today.

So go ahead and take a trip… Watch the videos and hear just how much can change when nearly 20 years separate THEN from NOW!