The 10 Most Popular Taylor Swift Songs According to AI

Dominique Harroch
Thu, 13 Nov 2025 20:56:06 +0000
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By Dominique A. Harroch and Richard D. Harroch

Few artists in modern music have redefined pop culture as profoundly as Taylor Swift. From her teenage country beginnings in Nashville to her global reign as a pop superstar, Swift has consistently reinvented herself while staying true to her gift for storytelling. She is not just a singer-songwriter but a cultural phenomenon—shaping conversations around music, identity, and fandom in ways few artists have achieved.

But which Taylor Swift songs are the most popular today? To find out, we asked AI to analyze streaming numbers, chart history, cultural references, and critical acclaim. The result was a data-driven list of Taylor Swift’s most enduringly popular songs across her career.

A Brief History of Taylor Swift

Taylor Swift was born in Pennsylvania in 1989 and, at just 14, moved with her parents, Andrea and Scott Swift, and her younger brother, Austin, to Hendersonville—a suburb of Nashville—so she could pursue her dream of becoming a country artist. Her 2006 self-titled debut album introduced her as a teenage country prodigy with breakout hits like “Tim McGraw.” Just two years later, with the release of “Fearless” (2008), she broke out beyond the country world and became a mainstream star, thanks to massive hits like “Love Story” and “You Belong With Me.”

Over the next decade, Swift reinvented herself repeatedly: embracing pure pop on 1989, exploring darker electronic sounds on “Reputation,” and later pivoting to intimate, stripped-back storytelling on “Folklore” and “Evermore.” Beyond her chart-topping albums, her ambitious Taylor’s Versions re-recording project reshaped conversations about artist rights, while her record-breaking Eras Tour became the highest-grossing concert tour in history.

Here are the tracks AI ranked as Taylor Swift’s most popular, along with their history, cultural impact, and accolades.

1. “All Too Well (10 Minute Version)” (Album: “Red – Taylor’s Version”)

Swift’s opus of heartbreak and detail-rich storytelling, this extended version instantly cemented itself as one of her most important works.

Year Released: 2021 (original 2012)

Genre: Pop Rock/Singer-Songwriter

Reasons for Inclusion: Masterclass in lyrical storytelling; cultural phenomenon upon release.

Impact on Pop Culture: Sparked viral discussions, short film adaptation, and cemented Red – Taylor’s Version as a landmark project.

Awards/Recognition: Won 2023 Grammy for Best Music Video.

2. “Love Story” (Album: “Fearless”)

A modern-day Romeo-and-Juliet narrative, “Love Story” catapulted Swift into global superstardom and remains one of the best-selling singles of all time.

Year Released: 2008

Genre: Country Pop

Reasons for Inclusion: Universal theme of forbidden love.

Impact on Pop Culture: Defined Swift’s crossover moment; beloved wedding song.

Awards/Recognition: Sold over 18 million copies worldwide.

3. “Shake It Off” (Album: “1989”)

Swift’s playful embrace of pop in “1989” was both a radio smash and a cultural reset, signaling her full break from country.

Year Released: 2014

Genre: Pop/Dance-Pop

Reasons for Inclusion: Infectious energy, massive commercial success.

Impact on Pop Culture: Empowerment anthem; inspired countless memes and covers.

Awards/Recognition: No. 1 on Billboard Hot 100 for four weeks.

4. “You Belong With Me” (Album: “Fearless”)

One of Swift’s most beloved teenage anthems, this track captured unrequited love with sing-along power.

Year Released: 2008

Genre: Country Pop/Teen Pop

Reasons for Inclusion: Universally relatable theme of longing.

Impact on Pop Culture: Defined her early career; music video became iconic.

Awards/Recognition: Won MTV Video Music Award for Best Female Video.

5. “Blank Space” (Album: “1989”)

Swift embraced her media persona as a “serial dater” with biting satire, crafting one of her sharpest pop tracks.

Year Released: 2014

Genre: Pop

Reasons for Inclusion: Clever self-awareness and reinvention.

Impact on Pop Culture: Music video became one of YouTube’s most-viewed.

Awards/Recognition: Reached No. 1 in multiple countries.

6. “Anti-Hero” (Album: “Midnights”)

The lead single from “Midnights” became a self-deprecating anthem that fans instantly embraced.

Year Released: 2022

Genre: Synth-Pop

Reasons for Inclusion: A vulnerable and witty look at insecurity.

Impact on Pop Culture: Viral TikTok sound with “It’s me, hi, I’m the problem, it’s me.”

Awards/Recognition: Swift’s longest-running Billboard No. 1 single.

7. “Cardigan” (Album: “Folklore”)

From her pandemic masterpiece “Folklore,” this indie-folk ballad showcased a new, introspective side of Swift.

Year Released: 2020

Genre: Indie Folk/Alternative

Reasons for Inclusion: New chapter in artistic evolution.

Impact on Pop Culture: Became a symbol of the “Folklore” era’s intimacy.

Awards/Recognition: Nominated for Grammy Song of the Year.

8. “Style” (Album: “1989”)

This shimmering pop track, inspired by her relationship with Harry Styles, remains a fan favorite and radio staple.

Year Released: 2014

Genre: Synth-Pop

Reasons for Inclusion: Timeless production and irresistible chorus.

Impact on Pop Culture: Defined the sleek aesthetic of “1989.”

Awards/Recognition: Certified multi-platinum worldwide.

9. “Enchanted” (Album: “Speak Now”)

Originally a fan favorite from “Speak Now,” this track surged to new life thanks to TikTok and the Eras Tour.

Year Released: 2010

Genre: Power Ballad/Pop Rock

Reasons for Inclusion: Expansive, cinematic sound.

Impact on Pop Culture: Viral resurgence in 2020s; highlight of Eras Tour.

Awards/Recognition: Cult-classic status elevated into mainstream.

10. “Cruel Summer” (Album: “Lover”)

Though originally a deep cut from Lover, “Cruel Summer” exploded in popularity years later, becoming a belated but massive hit.

Year Released: 2019 (chart peak in 2023)

Genre: Synth-Pop

Reasons for Inclusion: Quintessential modern Swift banger.

Impact on Pop Culture: Became one of the defining songs of the Eras Tour.

Awards/Recognition: Reached No. 1 on Billboard Hot 100 four years after release.

How AI Chose the Songs

AI ranked these songs based on several key factors:

Streaming Popularity: Plays on Spotify, Apple Music, YouTube.

Chart History: Billboard, U.K., and global charts.

Cultural Presence: TikTok virality, media references, and live tour moments.

Critical Acclaim: Reviews from major outlets and music polls.

Covers and Legacy: The number of times other artists have reinterpreted or sampled the song.

Final Thoughts on Taylor Swift Songs

Taylor Swift’s catalog is so vast that any “top 10” will inevitably spark passionate debate among Swifties. Some fans might argue for the inclusion of “Teardrops on My Guitar,” Wildest Dreams,” “Exile,” or “New Romantics.” That’s the beauty of Swift’s music: her popularity spans multiple genres, eras, and generations.

Still, the ten songs above capture Swift’s ability to combine diaristic songwriting with cultural dominance—making her one of the most important artists of our time.

Does this ranking line up with your favorite Taylor Swift songs, or would you find it impossible to limit your favorites to 10?

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About the Authors

Dominique A. Harroch is the Chief of Staff at AllBusiness.com. She has been the Chief of Staff or Operations Leader for multiple companies where she leveraged her extensive experience in operations management, strategic planning, and team leadership to drive organizational success. With a background that spans over two decades in operations leadership, event planning at her own start-up and marketing at various financial and retail companies. Dominique is known for her ability to optimize processes, manage complex projects and lead high-performing teams. She holds a BA in English and Psychology from U.C. Berkeley and an MBA from the University of San Francisco. She can be reached via LinkedIn.

Richard D. Harroch is a Senior Advisor to CEOs, management teams, and Boards of Directors. He is an expert on M&A, venture capital, startups, and business contracts. He was the Managing Director and Global Head of M&A at VantagePoint Capital Partners, a venture capital fund in the San Francisco area. His focus is on internet, digital media, AI and technology companies. He was the founder of several Internet companies. His articles have appeared online in Forbes, Fortune, TIME, MSN, Yahoo, Fox Business and AllBusiness.com. Richard is the author of several books on startups and entrepreneurship as well as the co-author of Poker for Dummies and a Wall Street Journal-bestselling book on small business. He is the co-author of a 1,500-page book published by Bloomberg on mergers and acquisitions of privately held companies. He was also a corporate and M&A partner at the international law firm of Orrick, Herrington & Sutcliffe. He has been involved in over 200 M&A transactions and 250 startup financings. He can be reached through LinkedIn.

Copyright © by Richard D. Harroch. All rights reserved.