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I'm How Old...? 27 Albums Celebrating Their 20th Anniversary in 2026

I'm How Old...? 27 Albums Celebrating Their 20th Anniversary in 2026

      Time is a fleeting, intangible concept. This is why, when we reflect on 2006 and the music that defined it, the memories appear both distant and familiar. However, the albums that surfaced in a time when genuine independent artistry flourished are hard to forget.

      These bold musicians saw the mid-point of the decade as a signal to break away from the mundane and conventional, exploring fresh ideas and embracing profound emotions. From J Dilla’s intricate, nostalgic soul music and TV On The Radio’s vibrant art-rock journey, to Beyoncé’s funk-driven RnB drama and Joanna Newsom’s enchanting baroque pop creation, as well as the blog rock debut of a Sheffield band—2006 was a remarkable year for innovators and their grand ideas.

      In this reflective list, the CLASH team has selected 27 albums from two decades ago that personally resonated with us, revisiting their brilliance and situating their significance. Dive in.

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      J Dilla – Donuts

      One of the most renowned albums of the post-Millennial period, the backstory of ‘Donuts’ has, at times, overshadowed the music itself. Famously crafted from J Dilla’s hospital bed while he was undergoing treatment for the illness that would take his life, it stands as a burst of unmatched creativity from a distinctive musical intellect. At once playful and intellectual, powerful and introspective, ‘Donuts’ defies categorization, offering a striking showcase of virtuosity that remains profoundly relevant. Robin Murray

      Cassie – Cassie

      Two decades ago, Cassie soared into the limelight with her self-titled debut album. This forty-minute work showcases her as an unassuming trailblazer at her peak, seamlessly blending early-2000s R&B with her signature sweet tones, thus paving the way for a new sub-genre of ethereal pop. Two decades later, it remains the highlight of her discography as renewed interest in her personal journey and Y2K culture brings us back to it. Zahra Hanif

      My Chemical Romance – Welcome To The Black Parade

      Twenty years ago, a single G note resonated worldwide, forever altering the landscape of emo. Responding to skeptics who predicted the band’s fleeting success, ‘The Black Parade’ became an immediate classic, a concept album grappling with themes of life, death, and all the drama in between. Its legacy is undeniable; in 2026, My Chemical Romance will be selling out arenas to perform the iconic album in its entirety. Vicky Greer

      Amy Winehouse – Back To Black

      Amy Winehouse resurrected vintage soul and infused it with raw emotion, combining Motown dramatics with tabloid honesty. ‘Back to Black’ is humorous, harsh, and devastating at every turn, rejecting tidy redemption narratives. Her distinctive voice pierced through the mix, delivering a timeless record of painful self-reflection. Today, ‘Back To Black’ serves as a template for emotional honesty in pop music, with its influence apparent in a new wave of artists, and its most quotable line continues to resonate with fans: “What kind of fuckery is this?” Irene Monokandilos

      Justin Timberlake – FutureSex/LoveSounds

      JT sidestepped the sophomore slump with an unconventional collection that hinted at RnB and pop retro-futurism. Primarily created alongside core collaborator Timbaland and his protégé Danja, Justin embraced a more intricate loverman persona that is more captivating than its individual elements. The album moved away from the spacey sheen prevalent in The Neptunes’ sound found on ‘Justified’, opting instead for a more expansive, tuneless, slow-burning sonic landscape that transformed into fresh synthetic forms. ‘FutureSex/LoveSounds’ likely stands as Justin Timberlake’s last truly great album. Shahzaib Hussain

      Taylor Swift – Taylor Swift

      Taylor Swift’s debut self-titled album is a cornerstone of her discography. Released when she was only 16, the youthful record firmly rooted itself in country-pop, establishing the tone for her work up to ‘1989’—with hints of those influences evident in later albums like ‘evermore’ and ‘folklore’. Cherished by fans and well-received during the acoustic segment of the Eras tour, this album merits its moment in the spotlight once more—and could potentially do so in 2025, as Swift has confirmed the re-record is complete. Amrit Virdi

      Beyoncé – B’Day

      Few albums in Beyoncé’s collection are as quintessentially “Beyoncé” as her sophomore album ‘B’Day’. Recorded in a mere two weeks—mirroring her character Deena’s emancipation in her breakout role in the musical Dreamgirls—‘B’Day’ fused vocal prowess with innovative, intense production; featuring sultry anthems like ‘Kitty Kat’, the urgent ‘Ring The Alarm’, the eclectic rock-soul of ‘Freak

I'm How Old...? 27 Albums Celebrating Their 20th Anniversary in 2026

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I'm How Old...? 27 Albums Celebrating Their 20th Anniversary in 2026

Time is an elusive and fleeting concept. This is why, when we reflect on 2006 and the music that defined that year, the memories it brings forth seem both far away and