Dissect Podcast: Last Song Standing S4 Finale

Episode: Crowning the BEST Album of the 21st Century | LAST SONG STANDING [Finale]
Date: September 16, 2025
Hosts: Cole Cuchna, Charles Holmes
Producer: Justin Sayles

Overview

The finale of "Last Song Standing" Season 4 embarks on an ambitious mission: to debate, bracket-style, and crown the single greatest album of the 21st century (so far). Hosts Cole Cuchna and Charles Holmes, together with producer Justin Sayles, pit iconic albums against each other—considering influence, artistry, cultural impact, and personal bias—winnowing down to the album that stands out as the definitive musical achievement of the past 25 years. The episode serves as a love letter to the transformative power of albums and the joy of music discovery.

Major Segments and Key Discussion Points

The Bracket: Albums in Contention

[00:53]

• Finalists:
  • Kanye West – My Beautiful Dark Twisted Fantasy
  • Beyoncé – Lemonade
  • Eminem – The Marshall Mathers LP
  • Daft Punk – Discovery
  • Madvillain (MF Doom & Madlib) – Madvillainy
  • Frank Ocean – Blonde
  • Kendrick Lamar – To Pimp a Butterfly
  • Solange – A Seat at the Table (Charles’s "cultural exchange" pick)
  • The Strokes – Is This It (Cole’s pick)

Charles:

“I think we have honestly as good of a list as we could have in terms of, like, matching influence and commercial impact with our own personal taste.” [01:31]

Pep Talk Cameos: A Moment of Levity

[02:16] - [09:07]

• Friendly competition declared: Charles wins trivia, receives "digital hugs" in the form of personalized Cameos.
• Cole receives pep talk from former Sacramento Kings draft pick Jimmer Fredette; Charles receives a freestyle video from rapper Riff Raff.
• The hosts contextualize these playful interludes as moments that highlight their friendship and the lighter side of obsessive musical debates.

Personal Top 10 Albums Revealed

[09:37] - [13:37]

• Both hosts share their (subjective) all-time favorite 21st-century albums before weighing cultural impact in the bracket debate.
• Charles’s picks range widely: Young Thug, Kanye, The Strokes, Fiona Apple, Rosalia, Usher, Arctic Monkeys, etc.
• Cole’s picks include Fiona Apple, Radiohead (two albums), Tyler, the Creator, Beyoncé, Daft Punk, Kanye, Frank Ocean, and Kendrick Lamar.
• Discussion highlights the tension between personal bias and broader cultural impact.

“It’s gonna show our biases going into the bracket... We can kind of check each other on trying to push for an album that we personally like and maybe losing some of the cultural context and stuff and being objective…” — Cole [09:37]

The Shortlist & Honorable Mentions

[13:44] - [17:51]

• Albums deliberated but not included: J. Cole (2014 Forest Hills Drive), Childish Gambino, Lil Wayne’s Tha Carter III, Missy Elliott, 50 Cent, Bon Iver, Outkast, Tame Impala, Amy Winehouse, Rihanna (Anti), Dilla’s Donuts, David Bowie’s Blackstar, Justice’s Cross, Death Grips, LCD Soundsystem, White Stripes, Charli XCX (Brat), and Taylor Swift.
• Debate on what makes an “album artist” and why popularity doesn’t always match with album influence.

"If this was the best song, best songs of the 21st century argument Outkast would have definitely been in there. But I think their best work was previous." — Charles [16:03]

The Bracket Battles: Quarterfinals, Semifinals, and Finalists

[18:10] - [54:39]

First Round

• Kanye West – MBDTF vs. Madvillainy:
  • Both hosts surprisingly agree: Madvillainy advances over MBDTF due in part to the way cultural attitudes toward Kanye have shifted, and Madvillainy’s unique lasting influence.

“I think Kanye west is the most important artist of the 21st century so far. But... I’m starting to value standing on your raps and standing on your art and standing on what you believe in…and I think we have learned in myriad ways that Kanye west doesn’t stand for anything at this point.” — Charles [21:19]

• Kendrick Lamar – To Pimp a Butterfly vs. Eminem – MMLP:

  • No contest: To Pimp a Butterfly wins on all fronts (ambition, cultural importance, artistry).

• The Strokes – Is This It vs. Daft Punk – Discovery:

  • Daft Punk’s Discovery “washes” The Strokes, serving as a pillar for electronic/pop music influence.

• Beyoncé – Lemonade vs. Solange – A Seat at the Table:

  • Deep debate: many argue Solange’s album is more influential sonically, yet Lemonade’s cultural monolith status is decisive.

Semifinals

• Madvillainy vs. To Pimp a Butterfly:

  • Madvillainy’s artistry is praised (Doom’s lyricism, Madlib’s beats), but To Pimp a Butterfly advances for its unparalleled impact, ambition, and thematic depth.
  • Reflection on how Kendrick’s art rises above the moment, becoming a multi-layered historic document.

• Daft Punk – Discovery vs. Beyoncé – Lemonade:

  • Both hosts ultimately agree Discovery deserves to advance—not only for its musical genius but for its far-reaching impact on the sound of the century.

Final Three: The Last Stand

• Frank Ocean – Blonde (automatic finalist)
• Kendrick Lamar – To Pimp a Butterfly
• Daft Punk – Discovery

“A good survey as much as you can through three albums of the 21st century and the story of it. So I'm glad actually we landed right here. I think the only thing missing is rock.” — Cole [60:14]

The Ultimate Showdown: Blonde vs. To Pimp a Butterfly

“Can an album that is dance and electronic forward, where what it is trying to do is different than a Blonde or a Pimp a Butterfly…compete?” — Charles [57:26]

On Kendrick Lamar’s To Pimp a Butterfly:

• An explicit concept record, weaving the fabric of 21st-century American turmoil and black experience.
• Regarded as “a chapter from a history book” ([68:31])—an album that will define a cultural moment for generations.

On Frank Ocean’s Blonde:

• Described as genre-defying, universal, and deeply emotional—a record that captures the ineffable feeling of being alive and searching for oneself in a complex world.
• The hosts agree no album better encapsulates the essence of the human condition, love, loss, and identity.
• Blonde’s independence—Frank’s industry-defying maneuvers—play into the album’s mythos.

“I think R B is one of the most disrespected musical genres in America...when I like if you would have told me as a kid ...that one of the most important albums... would be made by a black queer man that is coming from an R B tradition. I never would have thought it...to do it on an album and then for that album...to be transformative—is just like. It's, it's. It's the reason I do. Like, it's the reason I wake up in the morning.” — Charles [60:40]

“I can't precisely articulate what Blonde does to me emotionally, but every time I listen to it, it makes me feel things consistently throughout the entire thing. That's why I love music...for precisely moments like that.” — Cole [89:44]

On Daft Punk’s Discovery (third place):

• Although musically unmatched and foundational for the sound of the era, in the hosts' view, it doesn't move the soul like Blonde or encapsulate the historical sweep of To Pimp a Butterfly.

Decision: "The Last Album Standing" Is…

Frank Ocean - Blonde

[89:04]:

Cole: “Guys, I'm ready to call it. I'm going. I'm going. Frank Ocean's Blonde. Frank Ocean, last album standing.”
Charles: “I think we both agree that Blonde is the...has to be the last album standing of the 21st century so far.”

Memorable Quotes & Timestamp Highlights

• On shifting perspectives:
  “Historically, that is something that you are saying right now, because I think at one point in time, Twisted Fantasy would be unassailably the favorite of this entire exercise.” — Cole [20:05]

• On honoring different legacies:
  “Blonde feels like the more universally timeless album...the beauty of life. And I know it's a cliche to say, but there's—he's...he's able to...I mean, it's all about nostalgia and recoloring your memories, you know? And I think the beauty of Blonde...you just get the feeling of that beauty in the song itself.” — Cole [70:56]

• On album artistry:
  “It is some of the highest emotional highs listening to music I can ever. I've ever experienced, you know?” — Cole [77:18]

• On the music that endures:
  “When we started this, I was like, man, you know, this is...This season might be really too easy. We're not going to argue. This has been the musketeer...I can't believe. How are you feeling? Like we did it, bro.” — Charles [91:05]

Episode Structure – Timestamps of Key Segments

• [00:53] – Full finalist album list is revealed
• [09:37] – Personal Top 10 albums shared
• [13:44] – Cut shortlists & Honors explored
• [18:10] – The bracket and its matchups are presented
• [18:28] – The first round of debates commence
• [40:03] – Semifinals: Madvillainy vs. To Pimp a Butterfly; Discovery vs. Lemonade
• [54:39] – Final round: Blonde, To Pimp a Butterfly, Discovery
• [60:14] – Discussion zeroes in on Blonde vs. To Pimp a Butterfly
• [89:04] – The decision: Blonde is crowned the winner
• [91:05]-[94:55] – Reflections, thanks, and closing remarks

Concluding Thoughts

The finale is more than a competitive exercise—it’s a meditation on music’s purpose and the power of albums to mirror, shape, and transcend their era. The hosts weigh personal feeling, historic context, and technical mastery, admitting that any of the finalists could have worn the crown. Ultimately, Frank Ocean’s Blonde emerges not simply for its innovation or technical perfection, but for its stirring and transformative capacity to evoke the full spectrum of human feeling—a work both timeless and unmistakably of this century.

For newcomers and longtime fans alike, this episode is a potent reminder of the magic of a truly great album.