Winchester_At_Heart made the mistake of asking me about Taylor's best songs so I decided to answer the question with a chart, because the best of Taylor Swift is entirely dependent on your typical go-to music and your mood at the time.
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Taylor's made a lot of different types of music in the last 12 years, so I obviously couldn't just leave a list of 29 different songs with no explanation, because it wouldn't make sense. You can't put something pure and beautiful like "All Too Well" in the same category as something dark like "Bad Blood," so here's my solution.
Acoustic songs aren't necessarily acoustic, but you wouldn't notice anything off about it if Taylor played them acoustically. They're the quiet, beautiful ones with the best lyrics — like "When you take, you take the very best of me," from when she was 15, and things like "My mistake, I didn't know to be in love you had to fight to have the upper hand," "It turns out freedom ain't nothing but missing you," "Long were the nights when my days once revolved around you," "I'll watch your life in pictures like I used to watch you sleep, and I feel you forget me like I used to feel you breathe," and I'm gonna stop now because these all sound way better with music. Anyway, the acoustic category is my favorite.
Next is soft, which is the same type of feel, but there's more to the song than just acousticiness. Like, Enchanted sounds like the audio to literal sparkles. It's beautiful, and "Innocent" is the masterpiece Kanye didn't deserve. Case in point: 32-year-old Kanye West takes Taylor's award, Taylor sings, "32 is still growing up now." 26-year-old Taylor doesn't want to be called a bitch or let Kanye take credit for her fame when she had already outsold his entire discography by her second album, and Kanye has the audacity to start with the snake narrative. (I'm sorry, it's the 2 year anniversary of Kim's snake tweet and I'm still furious and the song just finished playing and ugh I'm emotional)
Cute is a little more upbeat than soft. It's finally crossing the line into not being a ballad, but they're still cute. "Haunted" is a masterpiece and deserved more than 65th place by Rolling Stone's rank of Taylor songs, and way more than 9 words on its beauty. I'd say this is where most of the later songs on "reputation" fit, but I just haven't gotten into them the same way I did these other ones.
Strong songs are actually upbeat, like "Style" and "Blank Space" but everyone knows those two so I didn't put them on here. Taylor had the audacity to leave "So It Goes..." off the set list for the rep tour but people complained and now it alternates with DWOHT for the acoustic performance before the surprise song and it totally deserves more but I'll take what I can get
Hard songs are the ones you jump around the room to and scream into your pillow because that goddamn Joe Jonas really had the audacity to sing "Now I'm done with superstars and all the tears on her guitar... the girl in front of me, she's so much better," well FUCK YOU JOE TWO CAN PLAY AT THAT GAME and yeah so Better Than Revenge is a good song even though Taylor says she's learned a lot since then and it's not a good way to look at the world and yada yada yada
And then I numbered them in a rough estimate of my faves on the lists (what no of course I didn't forget to number Cold As You) and I'm gonna say this is my actual tiered ranking of her songs
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(See you said no more than 20 songs so here's a list of 20 songs so technically I didn't fail)
Buuuuuut disclaimer: my rankings are, in no way, an accurate representation of Taylor's best songs. I grew up listening to "Mine" and "Sparks Fly" on repeat for hours at a time in my old radio playing with plastic cats, so I've kinda gotten tired of those ones. I'd sing "Change" a billion time's a day with my Wii Sing It game, so that one's gotten a bit old. I used to love the upbeat songs to death and skip all the slower ones, and now I've played out the upbeat ones and would rather listen to the slow ones (rep is the album I needed in 2012 and red is the album I needed in 2017 this isn't fair) so a lot of fan favorites are ones I have on autoskip in my mind. Essentially the entirety of the "Fearless" album or the unlisted songs on "Speak Now" are great if you're looking for more upbeat songs, and the rest of "Speak Now" and all the non-singles on "Red" are great if you like slow songs, and "1989" and "reputation" are great if you want pop songs (I swear not all of rep is like LWYMMD or ... Ready For It?) and yeah that's my long analysis of Taylor because I wanted to be thorough so you can find her best songs