Prior to his new album, Mr Morale & the Big Steppers, his first since the Pulitzer-winning Damn in 2017, we rate the best of an MC who has a claim to be hip-hop’s greatest

20. Wesley’s Theory (2015)

A crash course in To Pimp a Butterfly’s expansive sound – Thundercat’s bass ricochets around, George Clinton is on hand to bolster the P-funk-like chorus – and its lyrical viewpoint. It starts out like the standard bling-dripping, screw-you rapper’s victory lap, but suddenly flips into a troubled disquisition on materialism as a form of control.

19. Poetic Justice (2012)

Lamar has had a fractious relationship with Drake over the years – there are umpteen articles online picking apart their apparent lyrical references to each other – but all was harmonious on the standout collaboration from the LP Good Kid, MAAD City, replete with its fantastic Janet-Jackson-sampling beat.

18. DNA (2017)

DNA is Lamar in virtuosic form: a firework display of his technical ability as a rapper, shifting restlessly between viewpoints as he examines black identity. He apparently told the producer, Mike Will Made It, to make the backing sound “like chaos”; he responded with a patchwork of electronic noise and samples from Fox News – and of Rick James demanding drugs.

17. Cartoon and Cereal (2013)

Dropped from Good Kid, MAAD City and subsequently released as a single, the dark, Wu-Tang-goes-trap beat of Cartoon and Cereal improbably paired Lamar with the Rick-Ross-affiliated, swastika-tattooed rapper Gunplay. The directness of the latter’s verse is a perfect complement to the unpick-this density of Lamar’s lyrics.

16. Rigamortis (2011)

From Lamar’s debut album, a swaggering early example of his skills. Rapping in a double-time flow over a twitchy, sped-up jazz sample, he offers a stream of boasts about his ability that are so relentless and inventive, even Nas – one of the artists over whom Rigamortis appears to claim Lamar’s supremacy – called him “the future”.

15. i (2014)

Apparently Lamar’s favourite track from To Pimp a Butterfly, on which he gradually pulls himself out of depression into a state close to euphoria, buoyed up by a backing based on the Isley Brothers’ reliably joy-bringing That Lady. “What you gonna do?” he asks after detailing a litany of life’s horrors. “Lift up your head and keep moving.”

14. Element (2017)

It is obligatory for rappers to announce that they are the best, but the difference with Lamar is that he does it in a way that suggests he might well have a point. Hence Element, a post-fame restatement of the claims made on Rigamortis. Call me out on your track if you disagree, he suggests, but be warned: I will destroy you lyrically and, worse, “make it look sexy”.

13. Duckworth (2017)

Lamar in storytelling mode, albeit a story based on real events: his father’s 80s encounter with Anthony “Top Dawg” Tiffith, then a gangster, but ultimately the boss of Lamar’s record label. It is a complex, insightful and utterly gripping story, revolving around “one decision that changed both of their lives”.

12. Swimming Pools (Drank) (2012)

A perfect example of Lamar’s ability to turn a hackneyed style on its head. The chorus sounds like a nihilistic party anthem – “why you babysitting only two or three shots?” – his urgent rap involves peer pressure, puking and getting beaten up, a cameo from his conscience and an examination of the roots of alcoholism.

11. ADHD (2011)

A relation of Swimming Pools (Drank), this time homing in on drugs. Empathic rather than preachy, the verse where he recounts a conversation with a girl who has taken too much of everything is brilliantly, richly painted, with the spongy-sounding beat – a sample of Odd Future offshoot The Jet Age of Tomorrow – the perfect complement.

10. MAAD City (2012)

Without wishing to gush, Lamar is so good at what he does that anything in this Top 10 could reasonably be at No 1. Case in point: MAAD City’s intricate, perfectly handled six-minute story of his youth in Compton, which turns into a completely different track midway through and powers towards a nightmarish climax.

9. Sing About Me, I’m Dying of Thirst (2012)

Another Good Kid, MAAD City song in two parts – rapped from different perspectives, with different producers handling each section – it variously examines the responsibilities involved in using real people as material for songs, contemplates the worth of legacies and depicts the aftermath of a murder. It is dense and complicated material, done with seeming effortlessness.

8. The Blacker the Berry (2015)

A lot of To Pimp a Butterfly deals with pent-up emotions. The Blacker the Berry is the breathtaking moment when they explode, the album’s P-funk-y sound warping into something darker, the lyrics seething – “You hate me don’t you? You hate my people” – its rage directed inward and outward, the final verse offering a jaw-dropping twist.

7. Untitled 2 06.23.2014 (2016)

The standout from the interstitial demo collection Untitled Unmastered, Untitled 2 is of a piece with, and of the same standard as, To Pimp a Butterfly – free-blowing sax, a vocal that shifts from a prematurely aged quiver to something more strident, a lyric that dissects hip-hop’s obsession with materialism without exempting himself from criticism.

6. Money Trees (2012)

Over a dreamy sample from the indie band Beach House, Lamar vividly picks apart the bleak motivations behind his ambitions. His verses are fantastic, the hook by Anna Wise – from another indie band, Sonnymoon – is gorgeous and Jay Rock’s cameo is the sound of a man grabbing an opportunity with both hands.

5. King Kunta (2015)

You could argue that King Kunta’s lines dismissing rappers who use ghostwriters – presumably aimed at longstanding frenemy Drake – are a bit rich coming from someone who has worked with the ghostwriter-employing Dr Dre, but who cares when the G-funk-inspired beat is so inspired and infectious and Lamar’s rhymes so deftly handled?

4. Humble (2017)

Lamar at his most straightforward. Humble attracted a degree of controversy – the lines about the need for natural beauty deemed a bit male-gaze and judgmental towards women – but the track is irresistible: an earworm piano hook, a beat that shunts the song along, the lyrics taking one check-me-out shot after another.

3. Bitch, Don’t Kill My Vibe (2012)

At one point, Bitch, Don’t Kill My Vibe was mooted as a collaboration with Lady Gaga. Listening to the finished product, it is hard to see how that would have worked, not least because it is perfect as it is, the horizontal, stoned-in-the-sunshine music at odds with the fretful lyrics about fame and the state of hip-hop.

2. Backseat Freestyle (2012)

The best track on Good Kid, MAAD City – its rhymes, according to their author, bearing the influence of Eminem – Backstreet Freestyle offers an image of Lamar at 16 and as thorough a demonstration of his latter-day lyrical skills as you could wish for, his vocal constantly altering its speed and style.

1. Alright (2015)

As we have already established, you can happily swap the order of this Top 10 around as you please, but Alright grabs the top spot not just because of its Pharrell-produced quality, but also its impact. There is a theory that, in an age of social media, music can no longer wield the kind of epochal power it once did – there are too many other distractions. You get where that opinion comes from, but the sight of Black Lives Matter protesters – first in Cleveland, then across the US – chanting Alright’s chorus like a 21st-century equivalent of We Shall Overcome is a strong refutation: era-defining music for an era-defining moment.

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