The Best Part of Breaking Up: Taylor Swift's Greatest Hits

Generally I like to make compilations of my *own* favorite songs from one of my favorite artists. But then, most of my favorite artists have been playing for 30 years and have 20 albums. At this point in Taylor's career I'm really more curious about what her actual greatest hits album will eventually look like, because her legacy is still in the process of being written. So I compiled one.

The Best Part of Breaking Up: Taylor Swift's Greatest Hits

1. Love Story

2. We Are Never Ever Getting Back Together

3. Teardrops on My Guitar (Pop Version)

4. You Belong With Me

5. Mine

6. Today Was a Fairytale

7. I Knew You Were Trouble

8. Ours

9. Mean

10. Fifteen

11. Sparks Fly

12. Our Song 

13. White Horse

14. Begin Again

15. Back to December (Speak Now World Tour Live)

16. Should've Said No (Live in SoHo)

Deluxe Edition Bonus Disc

1. Highway Don't Care (Tim McGraw featuring Taylor Swift and Keith Urban)

2. Two Is Better Than One (Boys Like Girls featuring Taylor Swift)

3. Both of Us (B.o.B featuring Taylor Swift)

4. Fearless

5. Red

6. I Heart Question Mark

7. Eyes Open (Vh1 Storytellers)

8. Picture to Burn feat. Def Leppard (CMT Crossroads)

It's an interesting question. How do you approach an artist who already has so many important songs? How do you segregate the hits, when Taylor's entire albums chart? I'm not talking about on Billboard's Top 200 Albums, I'm talking about each track, individually!

Furthermore how do you mediate between Taylor's "country" side and her "pop" side? The songs that were hits on both sides of the aisle are easy, but then what do you do with songs that were #1 on the country chart, and only #65 on the Top 100? Or songs that were #15 on the 100, but didn't chart or underperformed in the country market?

I tried to be as objective as possible. The mitigating factors were sales, chart position, and longevity (thus far). And then I loaded up the bonus disc with interesting rarities while also using the opportunity to score a bunch of the biggest hits that hadn't been quite big enough to make the first cut.

It will actually be a lot easier to come up with an album like this in 10 or 15 years. A lot of midlevel songs that were genuine hits at the time, don't ultimately enter the cultural canon; and some songs that were minor hits upon release, end up becoming ubiquitous standards. Take Tom Petty for example, have you ever heard the song Jammin' Me? In 1987 that jaunty rocker was actually one of Tom's biggest hits. But it was left off of 1993's Greatest Hits and it has rarely (if ever) been played live after 1999. Meanwhile, believe it or not but American Girl didn't even chart in the US.

And that brings up another point: a greatest hits album wields influence. What's included and what's left off, can and will alter an artist's legacy. Hits left off the Best Of disc become deep cuts, and deep cuts that get included? Well, to new fans they're seen as hits. (See: Listen To Her Heart, Here Comes My Girl).

One issue that this really brings to light... Taylor is often accused of writing too many breakup songs. But here are all of her biggest hits, and most of them are love songs. Out of 24 songs here, only 8 of them could be considered breakup songs. That means 2/3rds of them *aren't* breakup songs.