The Swift Symphony: A Showcase Of Taylor’s 45 Most Successful Hits

By Ruby M January 21, 2024

Taylor Swift’s meteoric rise in the music industry has been marked by a string of noteworthy chart-topping hits that have solidified her status as a pop sensation worldwide. From her debut single, Tim McGraw, to the remarkable hit Shake It Off, and the profoundly moving Blank Space, Swift’s Billboard Hot 100 hits showcase her versatility and songwriting mastery. With numerous awards and accolades, including 10 Grammy Awards, Swift has consistently brought us both critically acclaimed and globally successful music throughout her discography. Beyond her musical achievements, the musical behemoth has also made headlines for her advocacy work, business ventures, and her ability to connect with fans on a personal level. This list highlights the lasting influence of Swift’s top-charting hits, emphasizing her influence on the industry.

Begin Again 

Peaking at a position of number 7, this song took its post in the top 10 upon its release and continued climbing upward. The Red hit was released in 2012 but is still a highly regarded fan favorite today in 2024. 


Swift told Good Morning America that the song is about “when you’ve gotten through a really bad relationship, and you finally dust yourself off and go on that first date after a horrible breakup and the vulnerability that goes along with all of that.”

Picture To Burn

This 2006 hit flew past the Top 40 benchmarks with a whopping number 28 peak in 2008. The hit was the fourth single from Swift’s 2006 self-titled debut album. A former friend of the hit singing sensation told interviewers some juicy tidbits about the song. 


Apparently, the angsty breakup song is about Jordan Alford – who went on a date and married a former friend. They were just kids when it happened – and 14-year-olds have fallouts over boys all the time. We wonder if they ever reconnected.


The 2022 Midnights track soared to number 6 on the Hot 100. It’s a song that narrates the protagonist’s frustration with her lover. According to sources, the singer was talking about her relationship issues with her then-boyfriend, DJ Calvin Harris. 


It is speculated that Harris did not value her as she felt she deserved, like in the song. In the song, the protagonist goes out on the town for a night, knowing that she can dazzle any room she walks into. Well, that’s not exactly untrue if you’re Taylor Swift.

Everything Has Changed FT. Ed Sheeran

This smashing duet featured on Taylor’s 2012 album, Red. After being released in 2013 as a single, the song skyrocketed to the number 32 spot on the Hot 100 after being released as a single in 2013. The song explores the realization that your life has completely changed after falling for someone new. 


The song features vocals from first-time collaborator and Swift’s good friend, Ed Sheeran. The song is rumored to be about Conor Kennedy, based on the secret message of Hyannis Port in the song – where Swift and Kennedy spent the 4th of July together.

Tim McGraw

Tim McGraw marked the start of Taylor’s superstar career. The country love song served as her debut on the Hot 100 chart, securing number 40. It was also the first of her many top 10 hits on Hot Country Songs.


Swift wrote the song in her freshman math class about a senior she was dating, Drew Dunlap, hoping to memorialize their relationship as she believed they would break up when he left for college. We wonder where is the guy now.

Midnight Rain 

The reminiscent 2022 Midnight track is about a relationship between Taylor and a small-town boy that ended because she needed to put her career first. Although the relationship is over – Taylor still thinks about the love she once had. 


The song was 5th on the Hot 100 in November 2022, which also contemplates a relationship characterized by stark contrasts, embodying the opposition between Sunshine and Midnight Rain. In this scenario, each harbors distinct desires and expectations from the relationship.

Eyes Open 

Eyes Open peaked at 19 on the Hot 100 after its 2012 release. The song featured as a single from Swift in the second installment of The Hunger Games: Songs from District 12 and Beyond and was later re-released in Taylor’s Version in 2023.


Taylor initially wrote the song for the soundtrack of the first Hunger Games film, but it didn’t make the cut. The lyrics imply that the song is about Katniss’s relationship with The Capitol, serving as a warning not to trust anybody.


This song is included in the album of the same title. Red is the prolific American singer-songwriter’s fourth studio album. Soaring to number 6 on the Hot 100, this song has been one of her most popular songs to date.


Fans believe that the song is about actor and former love interest of Swift, Jake Gyllenhaal, based on the assumption that the hidden message of the song “SAG” refers to Swift and Gyllenhaal or Sagittarius, the zodiac sign of both of them.


The 2010 deluxe edition Speak Now single debuted and landed on the 13th spot of the Hot 100. The song tells the story of a love frowned upon by others, but that doesn’t seem to bother the couple who are deeply in love.


The song’s music video features Zach Gilford as the female protagonist’s (played by Taylor Swift, of course) love interest – but despite the two being seemingly madly in love on screen, behind the scenes, the actor didn’t even know the singer’s first name – how embarrassing! 


This catchy song delves into Swift’s defiant retort towards her critics. It is rumored that the song specifically targeted music industry analyst Bob Lefsetz, who gave her a snarky review after a February 2010 performance with the legendary Stevie Nicks.


Mean debuted and peaked at number 11 on the Hot 100 in 2010. The song won Swift two Grammys in 2012, one for Best Country Solo and the second for Best Country Solo Performance. She showed the critics what she was made of.

Highway Don’t Care

That’s right – our favorite female singer teamed up with the subject of her debut hit for this hit track. The song was featured on the country singer’s 2013 album Two Lanes of Freedom and landed on the number 22 spot of the Hot 100. 


Three country stars collaborated on the song, blending relationships and road safety themes. Tim McGraw narrates a tale of a distracted driver who turns on the radio, featuring a fictional Taylor Swift song, to drown out her thoughts. Keith Urban contributes a guitar solo towards the song’s conclusion.


This 2008 Fearless track, deep-rooted in betrayal and heartbreak, is a shout-out to Swift’s best friend, Abigail Anderson. It went on to number 23 on the Hot 100 and resonated with teens worldwide. After all, we’ve all been betrayed in one way or another.


In the song, the country singer-songwriter recalls her freshman year at Hendersonville High, where she met her then-best friend during the ninth grade. The song’s lyrics explore the reality of being fifteen and the uncertainty that comes with teenage years.

All Too Well (Taylor’s Version) 

The 10-minute long track rerecorded in 2021 for the rerelease of Red (Taylor’s Version) soared to number 1, topping the Hot 100. The song topped the Hot 100 chart for the longest time. This was one of the rarer times people were willing to listen to a song longer than usual.


The song is regarded as one of Taylor’s most emotional songs of all time and is rumored to be written for actor Jake Gyllenhaal. The song is said to be one of fan’s most beloved songs in her entire discography.


22 was the 6th Red single to hit the Hot 100’s Top 20, claiming its spot as number 20 on the chart. The collaboration between Swift and Max Martin has been widely regarded as a fan favorite since its release.


Swift created the song to celebrate her 22nd birthday, and the hidden message in the album booklet reads, “Ashley, Dianna, Claire, Selena.” These names represent her friends: Ashley Avignone, Dianna Agron, Claire Kislinger, and Selena Gomez

Ready For It? 

Ready For It? It was during a college football game between Florida State and Alabama when this song debuted, and it quickly reached number 4 on the Hot 100 in September 2017 and made its mark as Swift’s 72nd Hot 100 entry.


She did what was unprecedented and bested the Beatles’ career total of 71 entries! The song contains dark and luscious production and sexually suggestive lyrics that are similar to her 1989 album in aspects of both sound and playfulness. 


The lead single from the singer’s eighth album, Folklore, launched during the Covid-19 pandemic and topped the Hot 100 after its release. The song was produced and co-written by The National’s Aaron Dessner. The music video found Swift shifting through different places via piano. 


Swift took extra precautions to adhere to the safety requirements of all involved. The shoot was overseen by a medical inspector, masks and social distancing were mandatory, and she was her own hair and makeup stylist for the shoot.


Released in 2019, the title song of the singer’s seventh studio album garnered significant public acclaim following a performance at the MTV Video Music Awards. As the album impacted the Billboard charts, the song was propelled to number 10, and fans were crazy for it.


Featured in Swift’s September 2019 Vogue cover story, the title track of was described as a “romantic, haunting, waltzy, singer-songwritery nugget.” Its release date was announced at the Teen Choice Awards, and it became the third track on the album.

White Horse 

This melancholic ballad galloped to a staggering number 13 on the Hot 100. The song received critical acclaim and was awarded Best Country Song and Best Female Country Vocal Performance at the 2010 Grammys. The re-recorded version was also well-liked by critics.


Swift drew on her encounters with love and heartbreak to write the earnestly emotional song, perfectly capturing the strong feelings surrounding a love gone wrong. The song was supposedly written about none other than fellow singer and once-lover John Mayer.

Today Was a Fairytale 

The romantic song that was featured on Valentine’s Day, where Taylor Swift and Taylor Lautner co-starred, skyrocketed to number 2 on the Hot 100 in February 2010, just missing number 1 due to Kesha’s TikTok bagging the spot on the chart.


Since the song was written around the same time as much of her album, Fearless,  the song was re-released in 2021 as part of Taylor’s re-recorded album, Taylor’s Version. Rumor has it that the song was for former flame Taylor Lautner.

Boys Like Girls FT. Taylor Swift – Two is Better than One

Pop-sensations Boys Like Girls collaborated with Swift on this 2009 single, which climbed to number 18 on the Hot 100. Swift co-wrote the song, a commercial success, and the second track off the Boys Like Girls album, Love Drunk. 


The song expresses the singer’s acknowledgment of the necessity of a specific person in his life despite earlier uncertainties. A reflective and somber piece, it is fundamentally a love story like others on the album but adopts a more vulnerable and delicate tone.


This lead single from Swift’s ninth album, Evermore,  Entered at the top spot on the Hot 100, maintaining the underrated folk singer-songwriter style from her preceding album, Folklore. Swift admits to choosing “Willow” as the starting track for the album.


She said that the decision stemmed from the enchanting and magical ambiance evoked by the music written by Aaron Dessner. Swift had hinted at the song title twice during the Folklore era – once on Instagram and another on Twitter.

Is It Over Now? (Taylor’s Version) [From the Vault]

Originally featured on Taylor’s 1989 album, this hit song became number 1 on the Hot 100 in November 2023. The song is notably intertwined with other tracks on 1989, including Style, Out of The Woods, and I Wish You Would.


Its narrative resurfaces later in Swift’s 2022 album, Midnights, particularly in songs like Question. The song explores the depths of heartbreak and self-reflection in a way that resonates with listeners, portraying moments of loneliness and memories from past experiences with a previous love.

Back to December 

This lovesick ballad entered and peaked at number 6 on the Hot 100 in 2010. It also went on to win two MBI awards for Publisher of the Year and Award Winning Songs and a Teen Choice Award for ‘Choice Break-Up Song.’


Like Today Was a Fairytale, this song was also rumored to be about Taylor Lautner – except unlike the romantic and loving lyrics of Today Was a Fairytale, Back To December takes a more melancholic approach to the short-lived romance between Taylor Squared. 


Delicate is the fourth single off of Taylor’s Reputation album. The song is a gentle ballad contrasting the first three singles on the same album. The song was likely written with Joe Alwyn in mind – Swift’s beloved back then.


The popular song stood at number 12 on the Hot 100 and slowly rose to the top of the Pop Songs airplay chart. The song also went to the top of Rob Sheffield of Rolling Stone’s 2017 Top 24 Songs. Our favorite singer can’t seem to do anything wrong.

Lavender Haze 

The Midnights’ opening track, Lavender Haze, draws from love-life experiences, encapsulating the bliss of a honeymoon-style relationship inspired by the 50s phrase. Stemming from a Mad Men episode line, Swift crafted the song to emphasize cherishing love’s passion over succumbing to external negativity.


The song climbed to number 2 on the Hot 100 chart and is confirmed to be about her relationship with British actor Joe Alwyn, with whom she had a 6-year relationship. The track was unveiled in Taylor’s TikTok game show, Midnight Mayhem With Me.

Me! FT. Brandon Urie

A complete shift from the somber tone of Reputation, Me! is a lively, celebratory track featuring Swift’s sugary sweetness alongside Panic! at The Disco frontman Brendon Urie. Fans clearly loved the duet, as the song soared to number 2 on the Hot 100.


The music video amassed 65.2 million views on YouTube within 24 hours, establishing it as the most substantial debut for a solo artist on the platform. It also shattered the VEVO debut record, previously held by the singer’s Look What You Made Me Do.

You Need To Calm Down 

This 2019 Lover cut reached number 2 on the Hot 100 chart. The singer, fueled by her advocacy for democratic political causes in late 2018, introduced an explicit democratic undertone into her music, starting with this song.


The lyrics of You Need To Calm Down supported LGBTQ, feminism, and self-empowerment causes. The music video included many LGBTQ stars and ended the multi-year feud with Katy Perry – with whom Swift reunited in an embrace on camera.

Our Song 

Taylor’s third-ever single, which debuted in 2007, became number 16 on the Hot 100 and was her first number 1 to date on Hot Country Songs. In total, the singing phenomenon has bagged 7 number 1s on Hot Country Songs.


Our Song was composed by Swift during her freshman year and was written about her then-boyfriend Drew Dunlap. Included in Taylor Swift based on its popularity among her classmates, Swift herself never anticipated it making it onto an album.

Teardrops on my Guitar 

Swift’s hit single climbed to the 13th spot on the Hot 100 in 2008. The song illustrates unrequited love, which Swift felt towards her classmate, Drew Hardwick, who would often allegedly ask her for dating advice about his girlfriend. That must have hurt for our favorite girl.


Later, in 2015, her unreciprocated lover was arrested for child abuse – so it’s probably a good thing that the two never got together despite Swift’s feelings for him. We can only imagine all the brouhaha it would cause. The song is certified 3 x Platinum by the RIAA.

Karma FT. Ice Spice 

The Midnights single soared to number 2 on the Hot 100 in 2023. The song was boosted by a remix and music video featuring Ice Spice and, as the name suggests, conveys themes of karma throughout the song. Indeed, what goes around, comes around.


This theme has recurred throughout Taylor’s discography – especially surrounding her infamous feud with Kanye West and Kim Kardashian in 2016. Taylor has mentioned numerous times that she believes karma is the most important life lesson to learn. We couldn’t agree more.


The lead single from Swift’s third studio album, Speak Now, tells the story of a girl who, due to her parent’s divorce, has a negative approach to love – but over time, falls in love with someone who convinces her otherwise, despite her fears.


The song made its mark as number 3 on the Hot 100 in 2010 and is allegedly about the late Glee actor Cory Monteith, with whom she had a brief fling – she was even spotted at the bowling alley with Monteith and Selena Gomez.

Look What You Made Me Do 

The primary track from Swift’s fifth chart-topping Billboard 200 album, Reputation, also secured her fifth No. 1 position on the Hot 100, attaining the peak in September 2017. The song targets celebrities with whom the star has feuded in recent years.


Fans speculate that the celebrities the song is aimed at are Kim Kardashian, Kanye West, and Katy Perry. The song’s music video made YouTube and VEVO history by amassing the most views within 24 hours. To date, it has more than 1.5 billion views.


Style hit the chart after the singer’s 2014 Victoria’s Secret fashion show performance, soaring to number 6 on the Hot 100. The third single from 1989 has been widely revered, with singer Lorde commenting that it’s her favorite song on the album.


Based on her dating history and the name of this song, the track is said to be about her fling with Harry Styles, with whom she shared a relationship back in 2012. By December 2015, the RIAA had bestowed triple platinum certification upon the song.

Wildest Dreams 

The enduringly successful collaboration of Taylor Swift, Max Martin, and Shellback resulted in the hit song Wildest Dreams, which in November 2015 peaked at No. 5 on the Hot 100. Known for its lush production and dreamy atmosphere, the song captivated listeners worldwide.


The ninth track and fifth single from 1989 delves into Swift’s desire for her lover to cherish their best moments even after the relationship concludes. The song captures a mix of emotions, conveying both a hope for longevity and an awareness of the inevitable end.

I Don’t Wanna Live Forever (Fifty Shades Darker) Ft. Zayn 

Following her 1989 era, Swift introduced the contemplative duet with Zayn as her initial post-1989 single. The song, featured in Fifty Shades Darker, ascended to number 2 on the Hot 100 in March 2017 – another success in her musical journey.


The song marks Swift’s inaugural release in 2016, outside of the singles from her fifth album, 1989. Simultaneously, it adds to ZAYN’s growing discography, released amid his debut album, Mind of Mine, launched in March of the same year.

Bad Blood FT. Kendrick Lamar

Propelled by a video showcasing Swift’s #squad and featuring a highly anticipated appearance by Kendrick Lamar, her diss track secured the No. 1 position on the Hot 100 for a week, shortly after the clip’s premiere at the 2015 Billboard Music Awards. 


Swift’s composition, Bad Blood, is widely acknowledged as a public declaration regarding her rift with Katy Perry. In this context, Kendrick Lamar’s verses might express his reflections on his haters. We all know haters are an insecure bunch who are your secret fans.

We Are Never Ever Getting Back Together

Following its release in 2012, We Are Never Ever Getting Back Together skyrocketed to number 1 on the Hot 100 chart and remained there for three weeks. The critically acclaimed single was a testament to Swift’s crossover appeal, marking her a top solo artist worldwide. 


The song also received a Grammy Award nomination for Record of the Year. Like many of her songs, this was written about former flame Jake Gyllenhaal, who allegedly told Taylor that listening to her album, Red, was a bittersweet experience.

I Knew You Were Trouble

Soaring to the third spot on the Hot 100 in October 2012, this track from the Red album peaked at No. 2. A global hit, it achieved top ten status in over a dozen countries, debuting at No. 3 in the U.S. with 416,000 digital sales.


Blending electropop and dubstep, this song signifies Swift’s notable shift from her country origins to broader pop influences. TIME recognized the singer as the “first major artist to fuse country and dubstep,” highlighting her influential transition. This song proves the Swift’s versatility.

Cruel Summer 

Receiving a single release four years after its debut on Swift’s 2019 album Lover, Cruel Summer still emerged as one of her major hits. In October 2023, the song achieved its pinnacle, topping the Hot 100 chart.


The song is rumored to be about the fragility of Swift’s relationship with Joe Alwyn, whom she first met when she was still dating Calvin Harris. Their relationship likely began soon after Harris and Swift split up. The couple made plenty of headlines before they split in 2023.

Love Story

The classic Romeo-Juliet love story retold in Taylor’s unique way became a musical masterpiece that peaked at number 4 on the Hot 100 chart. The song is part of her 2008 album, Fearless. It remains popular decades after its release.


Love Story was subsequently reissued as part of Taylor’s Version, along with the entire album. The song is rumored to be inspired by one of two individuals, Joe Jonas and Martin Johnson, both of whom she had brief flings with.

Blank Space 

Swift made history by outdoing and dethroning herself at No. 1 on the Hot 100 chart, as the second single from her 1989 album, Blank Space, replaced Shake It Off. It dominated the charts for seven consecutive weeks in 2014-15.


In an October 2015 interview with GQ, Swift revealed she penned the song from the viewpoint of the media’s portrayal of her as a “crazy, but seductive, but glamorous, but nuts, but manipulative” woman, offering a satirical reflection on public perception.

You Belong With Me 

A colossal hit, this track ruled the airwaves in 2009, reaching No. 2 on the Hot 100. Additionally, it achieved a groundbreaking feat by becoming the first country song since the chart’s inception in 1990 to lead the all-genre Radio Songs chart.


Love blossomed on the music video set where Hannah Montana’s Lucas Till co-starred with Swift. The two dated briefly but ended their romance when they realized they were better off as friends. Unlike her other exes, there wasn’t much drama between the two.


Midnights’ lead single made an impressive debut at No. 1 on the Hot 100, reigning for six weeks. Mariah Carey’s All I Want for Christmas Is You briefly displaced it on December 17, 2022, but the song reclaimed the top spot, totaling eight weeks at number 1. 


Anti-Hero became Taylor Swift’s ninth number 1 single and fifth to debut at the top. It, along with nine other of her Midnights tracks, collectively occupied the entire top 10, making Billboard history for the first time. The song is about the singer’s many insecurities.

Shake It Off

Swift’s anthem sought pop supremacy and achieved it spectacularly by embracing a devil-may-care spirit. Premiering at number 1 on the Hot 100 chart, it held the top position for an impressive four weeks, marking a significant triumph in her chart-topping success.


Its substantial nearly six-month presence in the top 10 significantly contributes to its status as Swift’s highest-charting single, a noteworthy achievement amid her myriad career milestones. The track’s impactful journey solidifies its legacy as a pinnacle in Swift’s charting success.

Should’ve Said No 

The final single of Swift’s 2006 self-titled debut album made its mark at number 33 on the Hot 100. The song was added to the album at the last minute and is about a former lover who cheated on the country pop singer. We need more juicy tidbits!


Apparently, Swift wrote the song in five minutes. The song is rumored (based on the secret message in the album lyric booklet) to be about Sam Armstrong, a high school flame with whom she had a relationship that went south.