Apologies for this epic post, I've been writing down my thoughts on this for weeks in preparation for the new album and this is the culmination!
I am really not sure how to answer the question about where to start listening to TS' back catalogue, I'm not sure that chronology is really the best guide and I think the best starter album will vary from person to person. I truly believe there is a TS album to appeal to most tastes so your best introduction to her music might be best informed by your existing music tastes.
On a purely personal level, I find it impossible to choose a single favourite album. What I have always found so remarkable about Taylor Swift is that she is simultaneously prolific and produces music of a consistently extremely high standard, a very rare combination.
With this in mind, the fact that I consider five of her albums to be perfect, utterly without flaws, is a testament to her incredible body of work as is the fact that there is not one single album of hers that I do not love with all my heart.
The five albums that I consider to be perfection are Reputation, folklore, evermore, Midnights and The Tortured Poets Department. I have arranged these here in order of date released so as not to give any hierarchy to my list as I love all of these five masterpieces equally. Each one is an incredible feat of song-writing and I feel really showcase Taylor's greatest skill, her amazing lyric-writing. In my opinion, she is the best lyricist in pop music history. evermore may have a slight edge over folklore, but I really couldn't call it I don't think. I should also add that I think it is really important to include all of the bonus Midnights tracks from the various editions when considering Midnights as a piece of work, since these are extraordinary too, the same could be said of the three bonus tracks spread between folklore and evermore. It seems silly to pick favourites from any of these albums as I consider them to be flawless. I cannot recommend any of her albums highly enough but, these five in particular, I would recommend to anyone wanting to embark on their TS journey!
Next on my list would be Lover. In my opinion, Lover contains some of the greatest songs TS has ever released, I am thinking particularly Cornelia Street, The Archer, Miss Americana, Death By A Thousand Cuts, I Think He Knows, False God and Cruel Summer. The only reason it ranks slightly below my big five is because it is, perhaps, a little more uneven than them, but still an outstanding album by any standards.
Next comes 1989. Of course 1989 is an unbelievable pop masterpiece,a glittering mirrorball of pop beauty and of course I adore every second of it but, for whatever reason, though it also contains some of my favourite TS songs, it doesn't quite make my top five. Maybe I have just heard Shake It Off and Bad Blood too many times, though they are still great songs. It goes without saying that you must listen to the definitive Taylor's Version of the album with the astounding bonus tracks!
My favourites on 1989 are Is It Over Now?, This Love, Style, I Wish You Would, Slut!, I Know Places, Blank Space, Out of The Woods, Clean, Say Don't Go, New Romantics, Suburban Legends and Now That We Don't Talk.
Next comes Speak Now. Is it controversial that I would place this slightly above Red? Maybe it is, but it is how I feel subjectively about this album which I think is just beautiful. My husband says it is over-long but I don't agree with that. There are some really wonderful songs on here and I think it marks a really pivotal moment in her career. Once again, please make sure to listen to the TV with the vault tracks!
Favourites from Speak Now: Sparks Fly, The Story Of Us, Back To December, Electric Touch, Castles Crumbling, Enchanted, Long Live, Better Than Revenge, Haunted and I Can See You.
Next is Red. It goes without saying that I love Red, probably the album that catapulted her to global stardom before 1989 made her a bona fide superstar. It is only a little below Speak Now for me because Speak Now just resonates more with me for some reason.
Favourite tracks on Red: All Too Well (10 minute version, naturally!), Holy Ground, The Last Time, Red, Starlight, Forever Winter, Girl At Home, Message In A Bottle, Begin Again, We Are Never Ever Getting Back Together and The Very First Night.
My penultimate choice is self-titled debut. I think this is an utterly delightful album full of charming songs. As I've said previously, I think TS is a peerless lyricist and, even though the lyrics on this debut, released when she was sixteen, are less sophisticated than her later efforts, I maintain all the hallmarks of Taylor's lyrical genius can be glimpsed here. It's just a really lovely album to listen to.
My favourite tracks on Taylor Swift are I'm Only Me When I'm With You, Should've Said No, Picture To Burn, Our Song and Tim McGraw.
Last, but definitely not least, is Fearless. I obviously love Fearless, not quite sure why it's slightly below the debut for me. No good reason really. It also marks out Taylor as a distinctly pop artist. There are still some country trappings but they are far less prominent than on debut.
My favourite tracks on Fearless are Love Story, Mr Perfectly Fine, The Way I Loved You, I'm Only Me When I'm With You, Hey Stephen, The Other Side of The Door, Fearless, Forever and Always, jump Then Fall and Come In With The Rain.
I'm not sure where The Life of A Showgirl will rank yet, I need to spend some more time getting to know it but, so far, I'm loving every second of it! It took me a while to properly become acquainted with TTPD, all thirty-one glorious tracks of it, and now I consider it amongst her best work, so I have high hopes for TLOAS!