Taylor Swift’s Career Is 18 Years Old: Here Are The Best, Worst, And FUNNIEST Highlights! 

Taylor Swift’s debut album, ‘Taylor Swift’ is 18 years old now, meaning that the queen of pop has been in our lives for as long. Swift is one of the most successful musical artists of all time. She is the first ever billionaire whose primary revenue is generated from music. After 18 years, 11 albums and 4 re-recorded albums, it’s undeniable that Swift has the staying power of icons like Michael Jackson, Madonna, Bruce Springsteen and the Rolling Stones. There is hardly a contemporary of Swift’s who can rival her level of influence and staying power. Love her or hate her, Taylor Swift is truly Miss Americana, 18 years reigning. 

Here are the best, worst, and weirdest career highlights of the great Taylor Swift: 

Best: The “Eras” Tour 

‘The Eras Tour’ is not only one of the most financially successful musical tours ever let alone of Taylor Swift’s career, it has also been a cultural phenomenon. Swift is still on the tour and when it concludes in December 2024, she will have played 152 3-hour shows across the entire world. Swift famously never cancels and has played for hours in pouring rain on multiple conditions. The commitment, athleticism, showmanship and discipline of Taylor Swift on her visually stunning show is truly above critique and despite being her most contemporary achievement might also be her greatest achievement of her entire career. 

Worst: Her relationship with Tom Hiddleston/Met Gala dancing 

Tom Hiddleston of Marvel fame and Taylor Swift met at the Met Gala in 2016 where they famously got caught doing this flirty little cringe dance on the backend of her relationship with Calvin Harris (who is mainly famous for dating Taylor Swift if he’s even famous for that). The two dated for about three months following the Met in what was the most oddly matched and not believable pairing of the last several decades. Most fans still seem unsure if that one was real or a PR stunt.  

Funniest: Her appearance in the film The Giver

The ironically forgettable movie adaptation of one of the most important novels of the 21st century, The Giver, featured none other than Taylor Alison Swift as Rosemary who was a prior memory receiver of The Giver (played by Jeff Bridges in the film) and also his daughter. The emotions associated with pain and joy were overwhelming to Rosemary who petitioned the government for assisted suicide and received it. In the movie, Rosemary sang and played piano, thus the use of Taylor Swift in the role. Swift did a fine job in the part, but the gravity of the material was a little lost by using a recognizable pop star in almost a cameo appearance. To be fair to Taylor, the movie could not find the emotional depth of the novel with or without her.

Best: The Bear season 2 episode 7, Forks

Taylor Swift was not in any episodes of The Bear but in what I consider to be a perfect episode of television serial, her song ‘Love Story’ was central to the episode titled Forks. ‘Love Story’ is arguably Taylor Swift’s most famous and immediately recognizable song and in fact it is so famous and recognizable it is arguably one of the most known songs of an entire generation (millennials). The use of the song in Forks (which is a coming of age episode) not only solidifies how transcendent the song is to a generation but it also encapsulates the song as a character in all of our lives. ‘Love Story’ in and of itself is really one of Taylor’s greatest career achievements but this particular episode of critically acclaimed (and stunningly beautiful) television highlights that achievement better than it standing on its own could. 

Worst: Her obsession with Kim Kardashian

Dating back to the time Kanye West told Taylor Swift “imma let you finish,” Swift has had beef with him and his ex-wife Kim Kardashian. After the “imma let you finish” episode, West sent Swift flowers and the event seemed smoothed over. But then he wrote his song “Famous” which has the lyrics “For all my southside n****s that know me best, I feel like me and Taylor might still have sex. Why? I made that bitch famous.” After the song came out, there was backlash from the Swiftie community and Taylor made a reference to it (negatively) in her Grammy acceptance speech. In an interview with a magazine, Kanye’s then wife Kim Kardashian said that actually Taylor Swift knew all about the song and the lyric so she wasn’t sure why she was pretending she didn’t. Taylor Swift’s PR team denied this and called the song misogynistic. Unfortunately for Taylor, Kim Kardashian had recorded the phone call and released that recording to the press proving that Taylor Swift absolutely knew about the song and the nature of the lyrics. 

Taylor back pedaled and said she didn’t know specifically about the word “bitch” being used in the song as if that was the point of controversy all along. Even though the entire time the army of Swifties never did anything but take her side, it was this episode that led to Taylor Swift’s belief that she is a victim and more specifically is a victim of Kim Kardashian. 

It’s been nearly 10 years since this all happened and Taylor Swift still seems to have a grudge. On her latest album, ‘The Tortured Poets Department’ there is a song called ‘thanK you aIMee’ which is about a bully who Taylor hates named ‘aimee.’ But the song titled is spelled so that you can clearly see it’s actually for Kim. It’s very weird for Taylor to still have this beef considering Kim and Kanye aren’t even married anymore and they haven’t said her name in many years. 

She needs to let Kim Kardashian go.

Funniest: Her appearance as in the movie Cats

Cats was a disaster all together but Taylor Swift’s role in the movie was one of the more troubling/creepy aspects of the film. Taylor played Bombalurina and for reasons totally outside her control, her cat, unlike any of the other cats, had huge human looking boobs and wore weird red high heels. It was unsettling to say the very least. She also wrote a new song for the movie, ‘Beautiful Ghosts,’ which was widely maligned because Cats already has a very famous score. What a time to be alive it really was when Cats released. 

Best: The “Red” Tour 

Before there was Eras there was Red. Swift’s ‘Red’ tour was really the first time she was truly considered a mega star. In fact, until ‘The Eras Tour,’ ‘Red’ was her highest grossing tour and the highest grossing country music tour of all time. Her Red album was when she began to transition more in earnest between country music and pop but the title song on the album was still definitely in country territory. With her iconic circus costume and the many surprise guests, ‘Red’ was the sensation that we now expect from Taylor. The Red tour is what really proved that she was an unstoppable cultural force. 

Worst: When she got political for the first time 

In 2018, Taylor Swift decided she wanted to get into politics. She did a poor job of it. She decided to back a democratic Senate candidate in Tennessee against Marsha Blackburn. The democratic candidate, whose name no one even remembers, obviously super lost the election and furthermore, Senator Blackburn is probably the leading voice in Congress for musicians rights and fair compensation. Swift claimed Blackburn was anit-gay or something. So Swift’s choice of when and why to get into politics was pretty flimsy. Then she made the big mistake which was to insult “Republicans” generally, ostensibly forgetting that nearly 50% of her fan base were likely Republicans. People got pretty upset. This is the actual moment when Taylor Swift became a villain to many as opposed to when she thinks it happened during the ‘Famous’ controversy. It wasn’t Kim Kardashian that sank Taylor’s ship. It was Taylor’s lack of political tact. 

She has since managed to hone her political message and keep it positive and away from supporters and more focused on candidates which is the savvier move. 

Funniest: That time she ran into Harry Styles in 2015 and it was so uncomfy

For a time, Taylor Swift was dating fellow pop singer Harry Styles. They broke up and then very soon after ran into each other at a hotel. In one of the most painful interactions ever caught by paparazzi, Taylor stares at her phone and tries to leave when Harry walks into the lobby but gets trapped into a group conversation. It was awful. And also very funny now in hindsight. 

Best: The 1989 album 

‘1989’ was Taylor’s first completely pop album and still considered one of if not the best of her discography. Despite not containing any country music which ties her to her original roots, most fans consider 1989 to be Taylor’s quintessential album and is still her best selling album of all time. Several publications of record place ‘1989’ as a top 10 album of its decade and more than one publication of record has placed it in the top 100 albums of essentially all time. ‘1989’ is without question a defining album for Taylor Swift and one that most consider to be important to music and culture. 

Worst: The time she said Travis Kelce was ‘metal as hell’

Fairly recently, Taylor Swift was being interviewed about her relationship with Travis Kelce. In the interview she recalled when Travis ‘put her on blast’ on his podcast New Heights. She said his doing so was “metal as hell” which are possibly the three cringiest words ever spoken by any human being ever of all time.

Funniest: Her relationship with Taylor Lautner 

At the height of Taylor Lautner’s Twilight fame, he and Taylor Swift briefly dated. If the fact that both of their names are Taylor wasn’t enough, they also appeared in the movie Valentine’s Day as an over-the-top couple where art and life were fully mirrored (they were both very funny in the roles). The two didn’t last long and Taylor Swift wrote the song ‘Back to December’ about Taylor Lautner which is to my knowledge the only one of her breakup songs that she assumes full responsibility. Flash forward many years and Taylor Lautner actually married a different girl also named Taylor. He made a guest appearance on ‘The Eras Tour’ and for seemingly no reason at all did a backflip on the stage. The Taylor squared love and friendship saga is really something. 

Happy 18 years, Taylor Swift! Long Live.