4. “Should’ve Said No”
We’re keeping with the revenge/breakup theme for this next single which is “Should’ve Said No.” As I said, I do love all of these songs so putting this one at 4 isn’t easy for me. This is another song that I remember listening to over and over again. There was so much bad scream-singing of this one.
However, “Should’ve Said No” edged out “Picture To Burn” for a few reasons. To me, this one is less of a revenge song but rather just telling the person how they wronged you and telling them why they shouldn’t have made that choice. Once again, it’s featuring that teen angst that I can’t get enough of from this album.
“Should’ve Said No” feels like a major “screw you” to the person who cheated and basically telling them that they should’ve thought before they did what they did. This one doesn’t actually have a music video but I’m sure some of my fellow Taylor fans will remember her iconic performance at the ACM Awards with the hoodie and the rain.
This was also one she performed with the Jonas Brothers in their 3D concert movie so it even has a fun remix. All in all, I feel like this one could even flip-flop with “Picture To Burn” but between the two, “Should’ve Said No” feels like it’s a better representation of the album and the era as a whole. If you disagree though, I’d love for you to share your thoughts on why in the comments.