20 Years of Taylor Swift: Greater Things Than Dating the Boy on the Football Team

August 25th, 2003. 13 years of age. I think I  might just live through this year. Two exclamation   points. I just hope I can keep up. My locker is  117 and my combination is 35 927. I love being   older. This year could be fun. I don't care what  people think of me now because I won't let them   bring me down. I think about this every day now,  but instead of it being like an intrusive thought   that hurts me, it's I can't believe this happened.  Like, how lucky am I? How grateful am I? At 16,   an album with her name on every song. At 20, album  of the year. Then three more. The biggest tour   in history. Every one of her masters in her  own hands. and the boy on the football team. Taylor grew up on a Christmas tree farm outside  Reading, Pennsylvania. We had like 15 acres," she   said later. Her dad Scott was a financial adviser  who ran the farm in his spare time. Her mom,   Andrea, worked in marketing, and Taylor has  a little brother, Austin. Music came from her   mom's side. Taylor adored her grandmother,  Marjorie Finland. Years later, she wrote a   song for her called Marjorie and wo Marjgery's own  old recordings into it. So her grandmother sings   on the track. Marjorie had sung in her high  school choir in Mexico, Missouri, and later   became an opera singer in Puerto Rico. She sang  with the Puerto Rico Symphony Orchestra and in   the Supper Clubs of San Juan and even hosted her  own TV show. She died in 2003 when Taylor was 13.   I'd open up my grandmother's closet and she  had beautiful dresses from the ' 60s. I wish   id asked her where she wore every single one  of them. She was a singer and my mom will look   at me so many times a year and say, "God, you just  you're just like her." She she died when I was 13.   I think it was when I was on a trip to Nashville  to try and make it and to try to hand out my demo   CD to record labels and things like that. But  one of the things about this song that kind of   um still rips me apart when I listen to it  is that she's singing with me on this song.   My mom found a bunch of her old records, a bunch  of old vinyls of her singing opera and I sent them   to Aaron and he added them to the song and wow.  So it says, you know, if I didn't know better,   I think you were singing to me now. And  it then you hear her, you hear Marjorie   actually sing my grandmother. When she announced  Evermore in 2020, the album with Marjorie on it,   Taylor wrote that her grandmother still visits me  sometimes, if only in my dreams. Taylor wanted to   sing country music and country music lived in  Nashville. So when she was 11, her mom drove   her there. Taylor remembered it this way. My  mom waited in the car with my little brother   while I knocked on doors up and down Music Row.  Nashville mostly said no. Taylor told that part   herself in 2022 when New York University gave her  an honorary doctorate. Having label executives in   Nashville tell me that only 35year-old housewives  listen to country music and there was no place for   a 13-year-old on their roster made me cry in the  car on the way home. Years later, she said not   listening to them was exactly why it worked. If I  were to look back and say, "Wo, that's crazy. This   is why this all worked." It was because I didn't  listen to the people who said that I didn't have   um a valid perspective on life because I didn't  fit into a certain demographic that they had   studied because of the analytics of a certain  genre and how people experience music. So her   family packed up and moved to Hendersonville,  Tennessee, just outside Nashville. Taylor knew   the move was for her. Andrea said I never wanted  to make that move about her making it. She didn't   want her daughter carrying that kind of guilt if  it never happened. My brother's a real bro for   doing that. Yeah, they all upended their lives.  For sure. It worked out well. At the 2010 Grammys,   Fearless won album of the year. Taylor was 20, the  youngest solo artist ever to win it at that point.   And she made sure to thank the families watching  back home. Our families are freaking out in their   living rooms. My dad and my little brother are  losing their minds in the living room right now.   And this is this is for my dad. Thank you  for all those times that you just you said   I could do whatever I wanted in life.  And uh my mom, you're my best friend. The girl who wrote about her locker combination  at 13 kept writing for years. In 2019,   Taylor opened those diaries to everybody. More  than 100 pages written from age 13 to 27 in   four special deluxe editions. A lot of them are  about her mom. Taylor once made Andrea a DVD for   her song The Best Day. And in 2007, she wrote  down how her mom reacted when they played it. There's a song I wrote called The Best Day that  is about my mom, and it's just hard to sing cuz   it makes me really emotional. And some of  them are about cats. In 2011, she wrote,   "Guess what I'm doing tomorrow? Getting a kitten."  That was Meredith Gray, a Scottish fold named   after the Grey's Anatomy Doctor. Olivia Benson,  named after the Law and Order SVU detective,   joined her in 2014. Taylor loves those cats and  she's never been shy about it. Why do you think   you're the most followed person on Instagram?  Because my cats are adorable. In December 2023,   Time named her person of the year, and she  brought a guest, her third cat, Benjamin Button,   a ragd doll she met on a music video set in  2019, was draped around her shoulders on the   cover. Her caption, Time magazine, we'd like to  name you person of the year. Me: Can I bring my   cat in 2026, she looked back at the best day,  the song she wrote for her mom as a teenager.   It's all written from the perspective  of a child singing about their mother,   but you never hear the word mom or mother or  mommy or anything like that. I never turned to   music to forget my human experience.  I turned to music to remember it. Her first single came out of math class.  That's where she got the idea for Tim McGrath.   She finished it after school with songwriter Liz  Rose in about 15 minutes and called it maybe the   best 15 minutes I ever experienced. It came out  on June 19th, 2006. When a friend called to say   they'd heard it on the radio, she wrote in her  diary, "God, I'm so lucky to be doing this." The   album came that October. It was simply called  Taylor Swift, and she wrote or co-wrote every   one of its 11 songs. By late 2009, it had spent  157 weeks on the Billboard 200. Tim McGra himself   admitted he was a little apprehensive about  a song with his name on it, and then he came   around and took her on tour. Her second album,  Fearless, came out in November 2008. Its single,   Love Story, crossed from country radio to pop  radio around the world, and it took her with it.   for her third speak now. She wrote every song by  herself. Her reason was simple. Ideas kept coming   at 4 in the morning and there's no one to call to  say, "Hey, do you want to write this with me?" So,   I just wrote all the songs by myself. Speak Now  sold more than a million copies its first week.   In a 2011 diary entry, she wrote that she'd like  to call her next album Red, and that's what it   became in 2012. Then in 2014 came 1989 which she  called her first documented official pop album.   In 2020 when the world shut down she made two  surprise albums folklore in July and Evermore in   December working mostly long distance with Aaron  Destner and Jack Antonoff. Folklore won album   of the year and Taylor became the first woman to  win it three times. Um but mostly we just want to   thank the fans. You guys met us in this imaginary  world that we created, and we can't tell you how   honored we are forever by this. Midnights came  out in October 2022 with the biggest week for   any album in nearly 7 years, and its songs filled  the entire top 10 of the Hot 100. And in 2024,   Midnight's won her a record fourth album of the  year. In August 2025, she announced her 12th   album, Sitting with Travis and Jason, holding a  mint green briefcase. This is my brand new album. We got TS12, baby. This is my brand new  album. It's called The Life of a Showgirl.   The Life of a Showgirl came out on October  3rd, 2025 with the biggest first week for   any album since sales tracking began in 1991.  Almost a year later came an expanded edition,   The Encore. If I look back at the song Timber,  there are actually sort of hints at at everything   that was going to happen in the next 20 years,  like character work. Like when it says he said the   way my blue eyes shined put those Georgia stars  to shame that night. I had never been to Georgia. One label in Nashville signed her. Scott Bquetta  was starting a brand new company called Big   Machine Records. Under that deal, the label would  own the master recordings of her songs. In 2018,   she moved to a new label and her first six albums  stayed behind. In 2019, they were sold to Scooter   Bronze Company, and Taylor said she found out  as it was announced to the world. A year later,   they were sold again, and she said, "This is the  second time my music had been sold without my   knowledge." So, she recorded all of it again. In  2021, she started putting out the re-recordings,   and she called them Taylor's version. When I did  my re-records, I started doing those in 2021. Mhm.   And most of the industry trades were like, "This  is a bad idea. This is her sort of derailing her   career in a way. Nobody's interested in you doing  the same album twice." Her fans were interested.   Red Taylor's version came with a 10-minute All  Too Well, and it became the longest song ever to   hit number one on the Billboard Hot 100. 1989,  Taylor's version sold even more its first week   than the original did, 1.653 653 million units.  Taylor later called the re-recordings defiant   reclamation of what was always mine to begin with.  Through those same years, her mom was fighting   cancer. Instead of a world tour for Lover, Taylor  planned just a few festival shows so she could   stay close to her. Then the world shut down and  the shows never happened. After the ERA's tour,   Taylor and her team decided it was time to try  to buy her original recordings from Shamrock.   The two people she sent were her mom and her  brother. They flew to Los Angeles, sat down,   and told them what the music meant to her. Then  they waited. It was a couple months after the   Super Bowl. We're in Kansas City. I get a call  from my mom. Um she was like, "You got you got   your music." And I just like very dramatically hit  the floor for real. On May 30th, 2025, she told   the world, "All of the music I've ever made now  belongs to me." This changed my life. Um, I can't   believe it still. And it changed things for the  artists coming up after her. I have so many new   artists come up to me now and say, "Hey, I didn't  even know this was a thing." And when I went to go   and negotiate for my record deal, I negotiated to  have my masters revert back to me after a certain   amount of years that I own them out. Quick pause.  If you love stories like this, like and subscribe   for more stories you can trust. And tell us  in the comments which era is your favorite. In 2014, she invited small groups of fans into her  own homes to hear 1989 before anyone else. and she   baked them cookies. She called them the secret  sessions. And she did it again for reputation and   lover. In 2010, when floods hit Nashville, Taylor  gave $500,000. When tornadoes tore through Middle   Tennessee in 2020, she gave $1 million and wrote,  "Nashville is my home." In 2023, she took every   one of her albums on the road in a single show,  one era at a time, The Era's Tour. The show ran   more than 3 hours with 40 plus songs and 16  costume changes. To get ready, she told Time,   "Every day I would run on the treadmill singing  the entire set list out loud, fast for fast songs   and a jog or a fast walk for slow songs." Then  came 3 months of dance training because she wanted   to be so overrehearsed that I could be silly with  the fans. It opened on March 17th, 2023. fans   started trading friendship bracelets, an idea from  a line in her song, "You're on your own, kid." In   Seattle, the crowd shook the ground so hard that  a seismologist measured it like a magnitude 2.3   earthquake. The Federal Reserve even mentioned  Taylor's concerts in a report on Philadelphia's   economy because the hotels were so full. when she  released the tortured poets department in April   2024 in the middle of the tour. She rebuilt the  show to add a whole new section for it starting in   Paris. In August 2024, three shows in Vienna were  cancelled after police stopped a planned attack   on the crowd. Taylor thanked the authorities  because we were grieving concerts and not lives.   She finished on December 8th, 2024 in Vancouver.  149 shows on five continents, more than 10 million   tickets, and over $2 billion, the highest grossing  tour in history. The concert film broke records,   too. The biggest concert film of all time. And  the tour book sold more than 800,000 copies its   first weekend. She took care of the cities, too.  On the Iris tour, food banks and city after city   got a surprise donation. In Denver alone, her gift  covered about $75,000 meals, and she took care of   her crew. In 2023, each of the nearly 50 truck  drivers on the tour got a $100,000 bonus. By the   end of the tour, she'd given about $197 million in  bonuses to just about everyone who worked on it,   from the dancers to the instrument techs, and  she wrote every one of them a note by hand. It was September 13th, 2009 at Radio City Music  Hall in New York. Taylor was 19 and she won her   first MTV Video Music Award, best female video  for You Belong With Me. Then Kanye West walked on   stage, took the microphone out of her hand, and  said Beyonce had one of the best videos of all   time. Taylor stood there holding the trophy while  the room booed. At first, she thought they were   booing her. Later that night, Beyonce won video  of the year and instead of giving her own speech,   she called Taylor back out. Backstage, Taylor  called it, so incredibly classy of her. In her   diary that week, she wrote, "Let's just say if  you had told me that Kanye West would have been   the number one focus of my week." In 2016, that  night came back around. Kanye released a song   called Famous with a lyric that called her a  crude name and took credit for her fame. And   he said she'd approved it. She said she never had.  Then a phone call between them was edited down and   posted online and it made her look like she was  the one lying. Then someone called her a snake on   social media and it caught on. In her diary that  August she wrote, "This summer is the apocalypse."   So she disappeared. She told time, "I moved to  a foreign country. I didn't leave a rental house   for a year. Nobody physically saw me for a year."  and that was what I thought they wanted. She came   back with an album called Reputation in November  2017. On the tour that followed, giant inflatable   cobras towered over the stage, and she wrote a  snake back to the main stage. She told the crowd,   "You might be wondering why there are so many  snakes everywhere. The thing they'd called her   became part of the show." In 2020, the full  phone call leaked. The line she'd objected to   never comes up in it. Taylor had been telling the  truth all along. Looking back on that album later,   she said, "When people decide we're all going  to stand around someone and point and mock them,   you can't respond with outward sincerity. When  I've gone through something that was like sort   of an attempt to drive me insane, when you when  you don't allow that to happen and you use art and   music as a way to barrel roll out of that, those  are the moments I'm the most proud of." In 2017,   she went to court in Denver. In 2013, a radio DJ  had groped her during a photo at a meet and greet.   When she reported it, he sued her. She counters  sued for a single dollar and she won. Afterward,   she said, "My hope is to help those  whose voices should also be heard." On July 8th, 2023, the IRS tour came to Arrowhead  Stadium in Kansas City and Travis Kelsey was in   the crowd. He'd made her a friendship bracelet.  He never got to give it to her and a couple of   weeks later he told his brother all about it  on their podcast. Speaking of Taylor Swift,   I know you went to the Taylor Swift concert.  How was it? Yeah. Well, I was disappointed   that uh she doesn't talk before or after her shows  because she has to save her voice for the 44 songs   that she sings. So, I was a little butt hurt. I  didn't get to hand her uh one of the bracelets I   made for her. You made her a bracelet? Yeah. If  you're if you're up on uh Taylor Swift concerts,   there are friendship bracelets and I received a  bunch of them being there, but I wanted to give   Taylor Swift one with my number on it. Taylor  heard about it. As she told Time, Travis very   adorably put me on blast on his podcast, which  I thought was metal as hell. On September 24th,   2023, she came to Arrowhead to watch the  Chiefs play the Bears and sat in the suite   right next to Donna Kelsey. By the time I  went to that first game, she said later,   we were a couple. I had a hat on and I had  a mask on and I'm walking in just in the   front. We're we're walking in with thousands  of people in Arrowhead and nobody noticed. You   manifested it. I did. You summoned me. Here  I am. She was all in. Football is awesome,   it turns out. She told Time, "I've been missing  out my whole life." In February 2024, she   played four nights at the Tokyo Dome, then flew  about 5,500 m to Las Vegas for the Super Bowl,   where Donna and Jason watched with her in the  suite. The Chiefs won in overtime. In August 2025,   she and Travis posted five photos with a caption  that read, "Like a small town wedding notice.   Your English teacher and your gym teacher are  getting married. On July 3rd, 2026, Taylor Swift   and Travis Kelce got married at Madison Square  Garden in New York. There were no bridesmaids   and no groomsmen. Just a best man and a man of  honor. Jason Kelsey was Travis's best man. And   Taylor's man of honor was her brother Austin, the  same kid who waited in the car on Music Row and   lost his mind in the living room when Fearless won  album of the year in 2010. Adam Sandler officiated   and they wrote their own vows. Paul McCartney  sang at the wedding too. The song was I want   to hold your hand. She did the greater things  and she married the boy on the football team. Heat. Heat. Um, I would love to tell you that this is the  best moment of my life, but I I feel this happy   when I finish a song or when I crack the code to  a bridge that I love or when I'm shot listing a   music video or when I'm rehearsing with my dancers  or my band or getting ready to go to Tokyo to play   a show. For me, the the award is the work. All I  want to do is keep being able to do this. At 16,   she put out an album with her name in the  writing credits of every song. In 2026,   she was voted into both the Songwriters  Hall of Fame in New York and the Nashville   Songwriters Hall of Fame, the youngest  songwriter Nashville has ever chosen.   She's been writing her own story ever since.  And the people who were there at the start,   her mom, her dad, and Austin are still  right beside her. Now, so are the Kelces. Enthusiasm can protect you from anything I would   know. Thanks for watching. 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