‘Last Song Standing’ Episode 6 Syllabus: ‘To Pimp a Butterfly’

Welcome to this week’s episode of Last Song Standing, a new show from The Ringer and Dissect built on a simple premise: two hosts figuring out an artist’s greatest song by debating their way through every album in the artist’s discography. Season 1 will tackle one of the most significant artists working today: Kendrick Lamar.

Each week, Cole Cuchna (host of Dissect and Key Notes) and Charles Holmes (from The Ringer Music Show and The Midnight Boys on the Ringer-Verse feed) will tackle a different Kendrick project, nominating three songs and ultimately picking one apiece. Then, they’ll take their individual picks into a season finale battle royale, in which they’ll have to determine which song should be crowned Kendrick Lamar’s best of all time.

On this week’s episode, we’re tackling Kendrick’s most acclaimed release to date …

To Pimp a Butterfly

Release date: March 15, 2015
Billboard 200 peak: no. 1
RIAA: 1x platinum
Singles: “I,” “The Blacker the Berry,” “King Kunta,” “Alright,” “These Walls”

Two and a half years after his breakthrough sophomore album, Good Kid, m.A.A.d. City, Kendrick Lamar returned with the project that would cement him as an all-time great. To Pimp a Butterfly—a 16-song opus that deals with race, growth, and exploitation—was hailed as an instant classic upon its release in early 2015. Years later, its star is no dimmer; when Rolling Stone issued its updated list of the greatest albums of all time in September 2020, TPAB came in at no. 19—nestled in between Kid A and Highway 61 Revisited.

TPAB achieved this despite having few breakout moments. “Alright” achieved a certain cultural cachet as a protest anthem, but otherwise, TPAB’s singles failed to do what GKMC’s did outside of the context of that album. Rather, TPAB is best viewed as a monolith—and a staggering one at that. Built on the production of Sounwave, Thundercat, and a score of other collaborators, it’s one of the most adventurous musical excursions in mainstream rap history, traveling from boom bap to P-funk to free jazz and back again. And atop that backdrop, Kendrick turns in a virtuosic performance, showing that the kid from the previous album was ready for adulthood and all that came with it. It’s the turning point in Kendrick’s career, and if it failed to reach the commercial heights of its predecessor or successor, it stands as a testament to his artistry. There’s a reason David Bowie cited it as one of the major influences on his swan song.

What the critics said at the time:

“Underneath the tragedy and adversity, To Pimp a Butterfly is a celebration of the audacity to wake up each morning to try to be better, knowing it could all end in a second, for no reason at all.” —Pitchfork

“The parts of this record I’m drawn to the most right now … sound like P-Funk’s Gaucho or Pink Floyd’s There’s a Riot Goin’ On.” —Grantland

Trivia: Kendrick originally planned to name the album “Tu Pimp a Caterpillar,” an acronym for Tupac, the late legend who Kendrick addresses repeatedly on TPAB.

How does the Last Song Standing team feel about To Pimp a Butterfly?

What Charles says: “A lot of stuff he does, I don’t agree with, but Kendrick has the right to say it.”

What Cole says: “[‘U’] is everything I admire in Kendrick Lamar—the vulnerability and bravery of expressing these very, very, very deep regrets is just so human.”

Possible choices for their lists: Will Charles and Cole choose the morality play of “How Much a Dollar Cost”? The anthemic “Alright”? “The Blacker the Berry”? “U”? Or will they opt for something else? Listen to find out.

Next week’s episode:

It all comes down to this. Charles and Cole will go head-to-head in the season finale battle royale, with one song emerging as Kendrick’s best of all time. Check back next Thursday on the Dissect podcast feed, and until then, check out the Last Song Standing companion playlist.

Hosts: Cole Cuchna and Charles Holmes
Producer: Justin Sayles
Production: Kevin Pooler
Theme Music: Devon Renaldo
Editorial assistance: Eduardo Ocampo

Subscribe: Spotify