Dissect: “good kid, m.A.A.d. city vs. To Pimp A Butterfly”

Podcast: Dissect (The Ringer)
Episode: LAST SONG STANDING | E7
Date: September 9, 2025
Host: Cole Cuchna
Guest Co-host: Charles Holmes

Overview

In the penultimate episode of Last Song Standing’s fourth season, hosts Cole Cuchna and Charles Holmes take on the most anticipated matchup yet: Kendrick Lamar’s good kid, m.A.A.d. city versus To Pimp a Butterfly. For the first and only time this season, both competing albums are by the same artist—a rule-break inspired by Kendrick’s unprecedented impact on 21st-century music. The hosts break down each record’s musicality, historical significance, and cultural legacy, then debate which deserves to advance to the season’s “Royal Rumble” finale.

Key Discussion Points & Insights

Setting Up the Showdown

• [00:07-1:26] Structure: Each episode features head-to-head album debates, with winners moving on to a “Royal Rumble” finale to crown the greatest album of the 21st century.
• [02:01-2:23] Rule-breaking: For the first time, both nominated albums are by Kendrick Lamar, “the most important artist… of the 21st century so far.”
• [02:23-04:35] Both hosts argue Kendrick has become the defining voice for modern hip-hop, even superseding contemporaries like Kanye and Drake.

“If I had to point to one rapper that is…the closest to becoming like a Jay Z figure? I would actually point to Kendrick.” — Charles (03:58)

Kendrick’s Place in the 21st Century

• [04:35-06:49] Reverence for tradition meets innovation: Kendrick synthesizes hip-hop history while pushing conceptual/sonic boundaries.
• [06:49-08:56] The rarity and impact of Kendrick’s release cycles and anti-microwaving ethos: He resists industry pressure to constantly drop music, instead prioritizing original, slow-cooked work.
• [08:56-09:13] Art vs. commercial trends: “It does feel like the art gets undermined…and it makes me so happy that Kendrick Lamar came out on top.” — Cole

Debating The Albums

Album Significance & Enduring Legacy

• good kid, m.A.A.d. city [10:30-18:33]

  • Released Oct 22, 2012. Features on the album: J. Rock, Drake, MC Eiht, Dr. Dre, and others.
  • Debuted at #2, has gone 3x Platinum, and stayed on Billboard 200 for years.
  • Critically acclaimed, although famously snubbed at the Grammys.

• To Pimp a Butterfly [63:13-66:55]

  • Released March 15, 2015. Debuted at #1, 11 Grammy nominations (most since Michael Jackson’s Thriller), enshrined in the Library of Congress, and ranked #19 on Rolling Stone’s 500 Greatest Albums.
  • Boldly political, sonically experimental jazz/funk/rap fusion. Not the expected “sequel” to GKMC—instead, a radical reinvention.

Thematic Weight

• [68:40-70:05] TPAB positioned as “an America album,” making visible the “rotten foundation” beneath the surface of the American Dream, particularly amid the Obama era’s allegedly “post-racial” narrative.
• [68:41] “Most artists, their second album is the ‘I saw the world, the fame album.’ This is Kendrick being like, I saw the world, I fulfilled the American dream…and now I’m seeing the rotten foundation.” — Charles

Category Showdowns

1. Biggest Song

• GKMC: “Money Trees”
  Key Points:

  • Not a single, but a massive streaming favorite and fan anthem (“1.9 billion streams on Spotify,” [23:21–24:00]).
  • Praised for its narrative integration, J. Rock’s standout feature, and longevity.
  • “The most enduring song…because it’s not trying to be a hit.” — Charles ([25:04])

• TPAB: “Alright”
  Key Points:

  • Unplanned single turned protest anthem, soundtracking Black Lives Matter rallies and protests ([79:08–80:09]).
  • “If you had to pick one song… it has to be ‘Alright’… through the lens of ‘Alright’ is how you talk about this album.” - Cole ([79:08])
  • Refrain “We gon’ be alright” encapsulates both personal and communal resilience.

2. Best Song

• GKMC: “m.A.A.d. City”
  Key Points:

  • Universally hyped centerpiece, live staple, and a microcosm of Kendrick’s artistry.
  • “It distills everything that Kendrick is—from narrative, to honoring West Coast hip-hop, to pushing it forward.” — Charles ([31:36–32:44])

• TPAB: “Wesley’s Theory”
  Key Points:

  • Academic-level complex album opener, mixing jazz, funk, and hip-hop while setting the album’s conceptual agenda.
  • “If ‘Wesley’s Theory’ doesn’t work, the rest of the album doesn’t work. It’s a thesis statement in the truest sense.” — Charles ([91:29–93:26])
  • Praised for its audacious non-conformity and boldness at the outset.

3. Worst Song

• GKMC: “Compton”
  Key Points:

  • Not a bad song (“He’s rapping his ass off”), just doesn’t fit the album’s emotional climax, feels “a little too tidy,” or “the cheesy song they play over end credits.” ([40:52–42:20])

• TPAB: “You Ain’t Gotta Lie (Momma Said)”
  Key Points:

  • Not outright disliked, but comparatively less compelling in production and energy.
  • “Probably my least favorite beat…if we’re forced to choose, this is the one I’d choose.” — Cole ([96:07])
  • The hosts resist calling out “Complexion” despite critiquing it, deferring to the importance of its message.

4. Best Deep Cut

• GKMC: “Sing About Me, I’m Dying of Thirst”
  Key Points:

  • Cited as Kendrick’s “storytelling magnum opus”; sparse, raw, and emotionally devastating.
  • “Every time I listen to it, I nearly cry.” — Charles ([43:09–45:37])
  • “If we’re just, in a vacuum, what’s the Kendrick Lamar song… this is the man—it is ‘Sing About Me.’” — Charles ([51:41])

• TPAB: “Hood Politics”
  Key Points:

  • Praised for energy, wit, and political subtext as “deep cut essence.”
  • “It’s just that classic, slumpy beat…classic Kendrick…aggression, and still staying on message.” ([102:57])
  • Excellent implicit critique of American party politics.

5. Best Cultural/Live Moment

• GKMC: Macklemore’s infamous Grammy “robbery” text ([55:56–58:07])

  • Symbolized the broader struggle for artistic recognition against institutional biases.

  “We didn’t need the Grammys to tell us this was great. Real people knew.” — Charles ([58:07])

• TPAB: The “All Right” era of live performances ([105:03–109:24])

  • BET, Grammys, and late-night runs transformed Kendrick into an icon beyond the music.
  • “That was the moment Kendrick Lamar was born, in terms of how we think of him today.” — Cole ([106:49])

Notable Quotes & Moments

• On making music outlast the churn:
  “Kendrick has proven that not only does good music last, but taking your time…if you slow down and really concentrate on what’s important, when shit sifts, you’re going to win.” — Charles ([08:56])

• On album structure brilliance:
  “He creates a concept record that stays true to the concept with every single song…yet he’s making hit singles.” — Cole ([27:42])

• On “Sing About Me”:
  “If any other rapper was on it, I actually…think it would have thematically taken away from it.” — Charles ([20:07])

• On the “alright” vs. “Money Trees” category face-off:
  “If you’re a mom in Middle America, you’ve heard ‘We gon’ be all right.’ To me, it’s about impact and importance.” — Charles ([111:05])

Album Trivia Highlights

GKMC:

• The planned feature for “Sing About Me” was Nas, but cleared samples and deadlines got in the way. ([19:06])
• “Money Trees” would be 7x Platinum if Kendrick registered all certifications (he notoriously doesn't). ([23:04-24:00])
• “Compton” was the first song recorded for album, written when Kendrick first entered the studio with Dr. Dre. ([21:38-21:39])

TPAB:

• The original album title was “Tu Pimp a Caterpillar” (TUPAC)—Kendrick settled on To Pimp a Butterfly, partly inspired by Anna Wise’s reading of “Conversations With a Butterfly”. ([70:27–71:16])
• Assassin’s feature on “The Blacker the Berry” happened because of a call from Canadian rapper Kardinal Offishall. ([72:13])
• “You” continues the personal narrative of Jason Keaton, also mentioned on “Uncle Bobby & Jason Keaton” from Kendrick’s EP. ([73:49])

Head-to-Head: Category Results

| Category | GKMC Winner | TPAB Winner | Consensus Winner | |------------------|-----------------------|---------------------|-----------------------| | Biggest Song | Money Trees | Alright | Alright | | Best Song | m.A.A.d. city | Wesley’s Theory | m.A.A.d. city | | Worst Song | Compton | You Ain’t Gotta Lie | You Ain’t Gotta Lie | | Deep Cut | Sing About Me... | Hood Politics | Sing About Me... | | Cultural Moment | Macklemore Grammy text | “Alright” anthems | Alright performances |

Final Tally:
Technically, by categories, good kid, m.A.A.d. city takes 3 out of 5. But both hosts pivot the debate to legacy and cultural impact.

The Judgment: Which Is the “More Important” Album?

• “good kid, m.A.A.d. city” is the better-crafted “rap album” and a perfect narrative record—smoother, more concise, but (by design) more intimate and less culturally expansive.
• “To Pimp a Butterfly” is the more ambitious, challenging, and resonant document. It’s the album that tells the story of the century and delivers not only musical heights but also a crystallizing portrait of America, blackness, politics, and art.

“If we’re trying to pick the best albums and the most important and influential and telling the story of the 21st century, I know I would pick To Pimp a Butterfly.” — Charles ([120:56])

“It is the story of the 21st century.” — Cole ([121:29])

Both agree:

• TPAB is the most essential album for this exercise—the one that best tells the story of the century—even though GKMC might be the perfect hip-hop record.

Final Reflections

• The hosts reflect on how time and personal growth have changed their relationship with both albums.
• They draw parallels to other “defining” albums of the season: Lemonade, My Beautiful Dark Twisted Fantasy, Blonde.
• They finalize cultural exchange picks for the finale: The Strokes’ Is This It and Solange’s A Seat at the Table.

“I returned to a lot of albums that were the foundation for why I became a music critic... what ‘To Pimp a Butterfly’ meant to me then, what it means to me now—it's changed. As Kendrick has matured, I've matured.” — Charles ([124:28])

Timestamps for Important Segments

• Kendrick’s Ascendancy & Why the Double-Nom: [02:01–09:13]
• GKMC Album Facts & Trivia: [16:20–18:33], [17:58–21:39]
• Category Battle—GKMC Best Song (“m.A.A.d. city”): [29:50–36:10]
• GKMC Deep Cut (“Sing About Me, I’m Dying of Thirst”): [43:09–51:41]
• Macklemore Grammy Text / Cultural Response: [55:56–58:07]
• To Pimp A Butterfly Facts & Context: [63:13–66:55]
• TPAB Thematic Discussion (Obama Era, Black Music, Protest): [68:40–70:05]
• Category Battle—TPAB Best Song (“Wesley’s Theory”): [91:25–95:18]
• Category Battle—TPAB Deep Cut (“Hood Politics”): [101:01–104:57]
• The “Alright” Phenomenon & Political Aftermath: [79:08–89:39]
• Final Head-to-Head Debate and Conclusion: [109:24–123:50]

Summary Conclusion

The debate between good kid, m.A.A.d. city and To Pimp a Butterfly is not about technical perfection but about the soul, ambition, and resonance of an album in the 21st century. The hosts crown To Pimp a Butterfly as the most important, influential document—one that not only reflected but helped shape the era. It left their “greatest album of the 21st century” finale stacked with modern classics and the heady sense that Kendrick’s influence will echo for decades to come.

Memorable Final Quote:

“If we’re just…in a vacuum, what’s the Kendrick Lamar song where you’re like, ‘this is the man, the artist, the thinker’? It is ‘Sing About Me, I’m Dying of Thirst.’ If you take that away, none of this is here.” — Charles ([51:41])