[Izulde]

After way too much thinking about this...

Taylor Swift
Album: 1989
The first true shift from country to pop, where she's been ever since. "Blank Space" and "Shake It Off" were both answers to people criticizing her for writing about previous relationships, so it does reference her earlier career. Also her best overall album.

The only greatest hits is some illegal Russian bootleg that doesn't count, so I'll put together a 10 track Greatest Hits:

1. "Teardrops on My Guitar" (Taylor Swift) - Most commercially successful single off debut album
2. "Our Song" (Taylor Swift) - Highest charting from debut album
3. "Love Story" (Fearless) - 6.5 million copies can't be wrong
4. "Back to December" (Speak Now) - First time she included an orchestra
5. "We Are Never Ever Getting Back Together" (Red) - One of her most famous songs and it entered the memestream - overall, I think this is her weakest album though.
6. "Shake It Off" (1989) - Smart, funny, successful, and a fantastic music video. Quintessential Taylor.
7. "Look What You Made Me Do" (Reputation) - Smashed Spotify rankings and in the category of Adele "Hello" and "Harlem Shake"
8. "Me!" (Lover) - Features a dude from Panic at the Disco. Jumped 98 spots in one week, a record
9. "Delicate" (Ryan Tedder remix) - Original song appeared on Reputation, but the remix takes it to another level imo
10. "Drops of Jupiter" (Cover in a concert) - Taylor does a lot of covers and this one is on there as a personal favorite - some of her vocals hearken back to her country roots, but it's still also very much contemporary