30. Cheers (Drink to That) (2011)
A buoyant paean to the quick-fix method of forgetting life’s worries by getting drunk, complete with big-up for the restorative powers of Jameson’s whiskey and a nod to Tyra Banks’s character in Coyote Ugly, Cheers (Drink to That) sounds elated and chaotic in equal measure: a messy night out in musical form.
29. Russian Roulette (2009)
The video for Russian Roulette featured Rihanna being gassed, shot and run over by a Porsche, but from the moment it kicks into life with a screaming guitar solo to its emotive final chorus, drenched in swirling synths, it offers high drama even without the disturbing accompanying visuals.
28. Kiss It Better (2016)
Kiss It Better was nominated for best R&B song at the Grammys, but in truth it’s a diversion into potent power balladry – laden with distorted guitar, it’s not too much of a stretch to imagine Cher singing it on the deck of a warship – albeit one given a hint of left-field weirdness by the primitive drum machine ticking away in the background.
27. You Da One (2011)
If not quite as spectacular as Man Down, You Da One’s attempt to meld dancehall and fluorescent 21st-century pop is still impressive, not least in the way it stirs dubstep into the sonic mix: the bass-heavy drop before the final chorus is genuinely exciting, shifting the mood of the track.
26. FourFiveSeconds (2015)
The unexpected sound of Rihanna collaborating not merely with Kanye West but Paul McCartney. Macca’s acoustic guitar drives the appealingly rough-edged and stripped-back FourFiveSeconds along, but it’s Rihanna’s vocal that makes the song come alive.
25. Don’t Stop the Music (2007)
It’s a gutsy move to riff on an idea already used on the biggest-selling album in pop history, but Don’t Stop the Music’s borrowing of Manu Dibango’s Soul Makossa – via Michael Jackson’s Wanna Be Starting Something from Thriller – worked perfectly: an insistent presence in the background of a powerful dance track. It’s also got a superb vocal melody.
24. Where Have You Been (2011)
If you want an example of the diverse influences that have gone into Rihanna’s singles over the years, look no further: Where Have You Been draws on I’ve Been Everywhere, a 1959 Australian country song once covered by – oh dear – Rolf Harris, transforming it into a gleaming, joyous bit of pop-house.
23. Love on the Brain (2016)
An anomaly even in Rihanna’s eclectic back catalogue, Love on the Brain delves into doo-wop and early-60s soul ballads, sampling Sam Brown’s Stop along the way. You could say it’s an example of post-Amy Winehouse retro pop, but it’s a superior one: an elegant, controlled performance, a lyric that darkly hints at violence.
22. Drunk on Love (2011)
Borrowing the echoing guitar sound of the XX quickly became a cliche in mainstream pop – “referenced at least every other session,” according to Ryan Tedder – but Drunk on Love’s sample of the trio’s Intro was inspired, adding a spectral edge to an epic confection of thundering drums and ravey keyboards.
21. Sex With Me (2016)
You can’t fault Rihanna’s self-confidence on this track, tacked on to the end of the deluxe version of Anti: sex with her is “amazing”, but her love rival is merely “alright”. The woozy, hedonistic swirl of its backing track perfectly captures the hedonistic mood referenced elsewhere: “Wrap up your drugs, come make me happy.”
20. Same Ol’ Mistakes (2016)
Same Ol’ Mistakes is a pretty audacious idea: rather than covering Tame Impala’s New Person, Same Old Mistakes, Rihanna just sang over the psychedelic original. But the result really works, digging out an influence at the song’s core: Tame Impala’s Kevin Parker was initially inspired by TLC. “It finally got the treatment it deserved,” he noted.
19. S&M (2010)
Too tongue-in-cheek to be the R&B Venus in Furs, the electro stomp that opened 2010’s Loud nevertheless reaffirmed that Rihanna had left her initial, rather sweet image behind for something more playfully provocative: “It’s so good being bad, there’s no way I’m turning back.” Avoid the remix – featuring poor Britney Spears – at all costs.
18. Hard (2009)
Produced by Tricky Stewart, who was responsible for Umbrella, Hard couldn’t be further from the singer’s 2007 megahit. It’s hip-hop-infused – Jeezy has a guest verse – driven by growling but triumphant-sounding electronic brass. And Rihanna’s in swaggering, powerful mode – and, given the line “that Rihanna reign gonna last for ever”, prescient, too.
17. Shut Up and Drive (2007)
A lyrical relative of the cars/sex metaphor of Grace Jones’ Pull Up to the Bumper, musically Shut Up and Drive is based on New Order’s Blue Monday, honing in not on the stammering drum machine or synths, but Peter Hook’s bass line, recasting it as taut, distorted new wave rock, an idea that works brilliantly.
16. Stay (2012)
Ballads are rarely Rihanna’s strongest suit, but Stay – written by, and featuring a high-pitched guest vocal from Mikky Ekko – is the exception that proves the rule, a lesson in avoiding emotional bombast, that less is more. Its simple piano line remains unadorned throughout, her vocal is direct and open and all the more powerful for avoiding histrionics.
15. Pour It Up (2012)
Either a song about visiting a strip club or “a hallucinatory metaphor for an identity crisis about sex and materialism” – according to cultural critic Camille Paglia – Pour It Up is a defiantly weird track: for all the cash-flashing braggadocio of the lyrics, Rihanna’s voice sounds numb, the music eerie and cold.
14. Disturbia (2008)
A track added to the deluxe version of Good Girl Gone Bad that ended up a Grammy-nominated single, Disturbia should be fizzy pop-house, but it’s stranger and darker than that: the sound is weirdly muted – even the hook feels low-key – Rihanna’s vocal even and understated, lending an authentic shiver to the lyrics: “Am I scaring you tonight?”
13. Needed Me (2016)
“Didn’t I tell you that I was a savage? Fuck your white horse and a carriage” is clearly a fabulous lyric, but Needed Me’s real draw is how off-kilter and creepy the music sounds: ghostly synths circle around, apparently out of time with the beat, its climax is a mass of disjointed vocal samples and growling, sinister bass.
12. Cockiness (Love It) (2012)
As attention-grabbing songs about cunnilingus go, Cockiness takes some beating: it’s alternately sexy, funny – “Keep it up boy, we can do this all day” – swaggering and urgent; the minimal production is great, the drawn-out sample of a male voice crying “You!” before the chorus a masterstroke
11. What’s My Name? (2010)
Rihanna’s early releases were steeped in reggae and dancehall, territory What’s My Name returns to, albeit viewed through the electro-pop lens of Norwegian hit-machine producers Stargate. The end result sounds humid and sultry, a song that slowly unwinds: Drake makes a guest appearance, but it’s Rihanna who sounds in charge throughout.
10. Bitch Better Have My Money (2015)
On which Rihanna turns her bad girl image up to 11. A stark, insistent, trap-infused single, co-written by Travis Scott, complete with a raw-throated vocal and fantastic, controversy-stoking video, Bitch Better Have My Money inhabits a different universe to her dance-pop hits, the thrilling sound of an artist doing exactly what she wants.
9. SOS (2006)
Producer JR Rotem’s speciality was audaciously making tracks out of samples that other producers might have discarded as too obvious, an approach that hit pay dirt with SOS, based on Soft Cell’s cover of Tainted Love. Obvious or not, it works to gleeful effect, Rihanna’s vocal weaving insistently around the instantly familiar riff.
8. Only Girl in the World (2010)
Only Girl in the World is a nailed-on pop-dance smash – the towering chorus means it couldn’t have been anything other than a huge hit – and more emotionally complex than it first appears: for all the fizzy elation of the music, the lyrics are alternately pleading and domineering.
7. Man Down (2010)
A fantastic single that served to set Rihanna apart from her peers, Man Down’s story of murder and regret was inspired by Bob Marley’s I Shot the Sheriff, its vocal emphasising Rihanna’s West Indian roots, its sound recalling reggae on the cusp of the dancehall era, the whole thing delivered with super-cool assurance.
6. We Found Love (2011)
Amid a glut of singles featuring R&B singers over a DayGlo EDM pop backing, Calvin Harris collaboration We Found Love stood out – for one thing, it’s just a better song than most of them; for another, its euphoria feels infectious rather than contrived. The vogue for this kind of thing is long over, but We Found Love still hits.
5. Work (2016)
Overfamiliarity might have rendered Work’s vocal hook slightly annoying, but that shouldn’t detract from the song’s counterintuitive greatness: it’s minimal, devoid of a chorus and featured a subtle interpolation from – of all things – Alexander O’Neal’s If You Were Here Tonight. And Rihanna’s response to Drake’s pleading – “mi nuh cyar if ‘im hurting” – is terrific.
4. Diamonds (2012)
Co-produced by Benny Blanco and Stargate, Diamonds takes an odd path to anthem status: it’s mid-tempo and oddly sombre-sounding and builds up without ever really reaching the expected exhilarating climax. But Rihanna’s vocal swings it: impassioned enough to invest Sia’s slightly cliched lyrics with genuine power.
3. Pon de Replay (2005)
The echo of old-fashioned 30s swing about its rhythm could have given Rihanna’s breakthrough single a whiff of novelty, but Pon de Replay was too strong a song for that. Its genius lies in its simplicity – there’s nothing but vocals, a rhythm track and some squealing synth – and the fact that every line feels like a hook.
2. Rude Boy (2009)
The album Rated R seemed to offer a plethora of references to Rihanna’s assault at the hands of then-boyfriend Chris Brown in 2009. That album’s Rude Boy, however, was the sound of someone moving into a position of power: the perfect balance between EDM-infused pop and dancehall toughness.
1. Umbrella (2007)
You could, of course, argue that Rihanna has recorded edgier and more experimental tracks since 2007, the year Umbrella topped the British charts for 10 weeks, and you would be quite right. But has she ever made a flat-out better single? From the minute Jay-Z’s terrible introductory rap slings its hook, Umbrella is an entirely perfect piece of pop music: in effect, an air-punching power ballad repositioned as minimal, icy R&B; its old-fashioned you’ve-got-a-friend sentiment somehow made more potent by her cool delivery, its vocal hook a simplistic masterstroke. It might have been interesting to hear what Mary J Blige made of the song – it was offered to her first – but there’s no way it could have been improved on.
• This article was amended on 1 April 2021. It previously incorrectly stated that Taylor Swift co-wrote We Found Love; she co-wrote a subsequent Calvin Harris and Rihanna collaboration, This Is What You Came For. And it is Mikky Ekko who appears on Stay, not Mykki Blanco as previously stated.