Quote from Alex Bobby on December 13, 2025, 7:11 AM

Taylor Swift appeared on The Late Show with Stephen Colbert, struggling to name her five favorite songs from her catalog. She chose “All Too Well (10-Minute Version)” and “Mirrorball,” reflecting on her evolving artistry and emotional connection to her music.

Taylor Swift, one of the most celebrated pop icons of her generation, faced a surprisingly daunting task during her appearance on The Late Show with Stephen Colbert on Wednesday, December 10. The challenge? To name her five favourite songs from her own expansive catalog — a question that left even the chart-topping singer momentarily stumped.

Swift, known for her meticulous songwriting and deep emotional storytelling, was quizzed by Colbert in a segment that has become a hallmark for the show: inviting musical legends to reflect on their careers. The segment is a playful yet revealing test, and the list of artists who have previously taken part reads like a who’s who of the music industry, including Dolly Parton, Elton John, Paul Simon, and Bruce Springsteen — all of whom are Rock and Roll Hall of Fame inductees.

For Swift, who has already amassed a record-breaking career filled with Grammy wins, multiple chart-topping albums, and a devoted fanbase, the task of narrowing down her favourites proved unexpectedly tricky. “This is so much pressure,” Swift admitted with a mix of humor and sincerity. “You’re already writing five,” she added, highlighting the internal conflict of evaluating her own work — something that even seasoned artists can struggle with.

The Challenge of Choosing Favourites

For an artist like Swift, whose career spans more than a decade of meticulously crafted music, choosing just five songs is not just a casual pick — it’s a personal reflection on moments, memories, and artistic milestones. Swift candidly explained that the challenge requires not only remembering her catalog but also appreciating her work in a new light.

“I think I require a little bit of time to like, appreciate my work in a way… and it’s constantly changing, right. It’s a little too soon,” she told Colbert. This self-awareness underscores the complexity of her artistry — an ability to continually reinterpret and re-experience her own creative journey.

Despite the difficulty, Swift was able to select a few standout tracks that hold a special place in her heart. Her first pick was “All Too Well (10-Minute Version)” from Red (Taylor’s Version), released in November 2021. The song, widely regarded as one of her most emotionally intense pieces, has resonated deeply with fans and critics alike. Swift called it her first definitive choice, reflecting her pride in the storytelling, vulnerability, and painstaking attention to lyrical detail that defines the song.

She also chose “Mirrorball” from her 2020 album Folklore, a record that marked a bold shift in her artistic style toward indie-folk and introspective songwriting. Swift described her current obsession with The Life of a Showgirl, hinting at the continuous evolution of her tastes and the songs she finds herself gravitating toward at any given moment.

However, despite these selections, she admitted, “I can’t really do any of the others,” leaving the rest of the list unfinished. Fans on social media immediately empathized with Swift’s predicament, praising her honesty and relatable struggle of selecting favorites from a body of work that spans hundreds of songs.

Reflecting on a Legendary Career

Swift’s segment on Colbert was not just a test of memory or preference — it was a window into the mind of an artist constantly in motion. Over the years, she has reinvented herself multiple times, moving seamlessly between country, pop, indie, and alternative sounds. Each album represents a distinct era, a reflection of her personal and artistic growth.

From Fearless to 1989, Red to Midnights, Swift’s discography is a sprawling narrative of heartbreak, empowerment, and introspection. Asking her to select just five favorites is akin to asking a painter to pick just five favourite brushstrokes — it’s deeply personal and subject to change depending on the moment, mood, or even the day.

Colbert’s quiz, while lighthearted in nature, revealed something profound about Swift: her humility and thoughtfulness in evaluating her own work. While millions of fans around the world may have their own definitive lists, Swift’s answers highlight the artist’s continual dialogue with her craft, the stories she tells, and the emotional weight behind each song.

Fan Reactions and Cultural Impact

Swift’s candidness sparked excitement and discussion among fans and music enthusiasts alike. Social media platforms were flooded with speculation about what her remaining picks might be and debates over the songs that hold the most cultural significance in her career.

Beyond entertainment, the segment serves as a reminder of Swift’s influence on modern music, her ability to connect with audiences across generations, and the level of dedication she brings to her songwriting. Her hesitation to finalise her list also humanises her, making even a global superstar relatable in her indecision.

A Moment for Reflection

For Swift, the Colbert segment was a rare moment to pause and reflect on her journey — a journey that has already solidified her place among music’s greats. With accolades ranging from multiple Grammy Awards to record-breaking streaming numbers, and the anticipation of future recognition such as potential Rock and Roll Hall of Fame induction, she continues to balance critical acclaim with personal artistry.

The question of her five favorite songs is more than a trivia challenge; it’s a glimpse into how she values and revisits her own work. Swift’s honesty about the difficulty of picking highlights her constant evolution and connection to her music in a deeply personal way.

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Conclusion

Taylor Swift’s appearance on The Late Show with Stephen Colbert showcased not only her humor and charm but also the thoughtful approach she takes to her artistry. While she struggled to select her top five songs, the process revealed her ongoing engagement with her own catalog and the emotional resonance her music holds for her. As fans eagerly await the rest of her picks and continue to celebrate her expansive discography, it’s clear that Swift’s creative journey remains as compelling as ever — constantly evolving, deeply personal, and resonant across generations.