Justin Timberlake’s 20 Best Songs, Ranked

By Eóin Donnelly

Usher, David Beckham, Leonardo di Caprio, André 3000, Conor McGregor, Andrea Pirlo, A$AP Rocky, Dwayne ‘The Rock’ Johnson and The Weeknd are just some of the names that come to mind when posed with the eternally perplexing question: who is the coolest man alive? I guess this is as good time as any to plug our ‘Coolest Man Alive’ Spotify playlist. Ahead of the release of his fifth album Man of the Woods tomorrow and his half-time performance at the SuperBowl on Sunday, we count down the 20 greatest songs ever released by one of the most effortlessly suave men to ever grace a microphone: Mr Justin Timberlake.

20. Last Night

As great a singer as Justin Timberlake is, things are certainly made easier when you’ve had producers of the calibre of The Neptunes by your side for your whole career. One of many Pharrell Williams and Chad Hugo beats on this list, ‘Last Night’ finds Timberlake playing the scorned lover role that was so prevalent on Justified. For a man so angry, this song sure sounds pleasant. Even when he’s in his worst mood Justin exudes sensuality.

19. Love Never Felt So Good (with Michael Jackson)

I’m dead against posthumous albums. The perfectionist standards of music’s most beloved auteurs is maintained by a diligent dedication to quality over quantity, and the unauthorised release of unfinished music hidden away for years on hard drives is capitalism at its ugliest and most unrestrained. Every so often however, a song breaks through beyond the grave that matches that exalted standard. 2Pac’s ‘Changes’ and Bob Marley’s ‘Buffalo Soldier’ comes to mind, as does this funky collaboration between Timberlake and the King of Pop that’s sure to be a mainstay on wedding playlists for years to come. A song with a name like this has to be irresistibly catchy and undeniably fun. Mission accomplished.

18. Strawberry Bubblegum

Like a-ha’s iconic ‘Take On Me’ video, this is one of those songs you just want to live in. Miguel’s ‘Pineapple Skies’ was definitely influenced by Timbaland’s infectious groove. I don’t know what ‘Strawberry Bubblegum’ means and I don’t wanna know. I’d like to think he’s singing about something so beautiful, it can’t be expressed in words, and it makes my heart ache because of it. I tell you, his voice soars higher and farther than anybody in a gray place dares to dream. Yeah, I did steal that from Morgan Freeman.

17. Suit & Tie (feat. Jay-Z)

“Don’t leave while you’re hot, that’s how Ma$e screwed up”, Kanye West rapped on ‘Devil In A New Dress’, referencing the Harlem rapper exiting the big-time to become a minister at the top of his game. It’s a pity Kanye’s wisdom was arriving in 2010 rather than 2006, a time when Justin Timberlake established himself as the world’s biggest popstar only to take a hiatus from music in favour of acting. Unfortunately, he’s yet to recapture the heights of 2006’s revolutionary FutureSex/LoveSounds. ‘Suit and Tie’ marked his first single in six years, a jazzy maturation of the classic Timberlake sound that’s custom-built for tuxedos and whiskey. At his best, he can still pack more cool than an Alaskan freezer.

16. Set the Mood Prelude / Until the End of Time

Bruce Springsteen’s ‘Cover Me’, from his legendary 1984 album Born In The U.S.A., is a fantastic piece of songwriting about taking refuge in the arms of a lover in crazy times. Timberlake’s ‘Until The End of Time’ follows a similar pattern to a much more tranquil backdrop that befits the solace he seeks: “I woke up this morning/ And heard the TV sayin’ something/About disaster in the world and/It made me wonder where I’m going/There’s so much darkness in the world/But I see beauty left in you girl/And what you give let’s me know/That I’ll be alright.” Sometimes that’s all you need.

15. Ayo Technology (with 50 Cent)

Coming out on the losing side of a highly-publicised sales war with Kanye West’s Graduation, September 11 2007 effectively ended 50 Cent’s career and altered rap’s hitherto gangsta archetype forever. That is to take nothing away from Curtis’s fourth single. “I’m tired of using technology/I need you right in front of me” is a hook made for 2018’s hyper-digital romantic battlefield. Keeping in mind Timbaland’s prototypical futuristic production which hasn’t aged a minute, if this came out today it would be a global smash.

14. Take It From Here

If I’m ever on a desert island I hope I have an iPod full of Neptunes beats. Pharrell Williams is a madman. Atop a suitably breezy instrumental built on languid guitars and cascading strings, Timberlake flexes his best naturalistic metaphors: sun, lakes, skies and air- it’s all there. Justin’s at his best when he lets his vocals do the talking.

13. SexyBack (feat. Timbaland)

I’ll always associate this song with the ultimate rite of passage… teenage discos. Back when I was getting my first bad checked shirt and even worse brown shoes on, this was the biggest song on the planet. It takes a man of unparalleled swagger to boldly proclaim he’s “bringing sexy back” and not cause a single snigger. As a first single of Timberlake’s sophomore album, ‘SexyBack’ was a reinvention of sorts, the electric basslines eradicating the boyish charm of debut Justified in favour of a brash, bad-boy edge. Teetering on the edge of cringe-worthiness, Timbaland’s ad-libs (“Look at those hips”, “Let me see what you’re twerking with”) would ruin a lesser track, but such is the bankability of Timberlake’s Cool Factor that it never even mattered.

12. Signs (with Snoop Dogg & Charlie Wilson)

I’ll say it again: Pharrell Williams is a madman. Like ‘Suit & Tie’ on steroids, ‘Signs’ is a fantastically flamboyant, feel-good G-funk masterpiece that deserves compulsory status at every party on the planet. It surprises me how little this song gets played today. One of the most forgotten gems of the 2000’s, the funky recipe cooked up by Snoop Dogg, Uncle Charlie and Timberlake is a dancefloor-ready banger that will have even the shyest of wall-dwellers dropping it like it’s hot.

11. Summer Love

The Prince influence is strong with this one. These synthesisers sound like they were plucked straight from The Purple One’s 1999. Far from pastiche plagiarisation, Timberlake’s trademark blend of hip-hop flows and falsetto come-ons adds tenderness to a beat that’s much nastier than the title suggests.

10. FutureSex / LoveSound

A great album opener should set the tone of what’s to come. When you click play on Justin Timberlake’s second and best album you know exactly what you’re in for. He takes his time, easing himself into Timbaland’s lavish bass soundbed with restrained allure before the track explodes with kaleidoscopic charisma, taking listeners in more directions than the average Eden Hazard mazy run. Rarely has a song so fitted its title.

9. What Goes Around… / Comes Around (Interlude)

A versatile pen is an essential feature of any artist’s longevity. One of the most vital songs on FutureSex/LoveSounds, this dejected lesson in karma is a much-needed offset to the empty carnal desire that typifies the album. You always need at least one song for the puritans. Often seen as a sequel to 2002’s ‘Cry Me A River’, ‘What Goes Around…’ is proof of Justin’s ability to sing about matters of broken hearts in addition to producing songs to break the bed. Speaking of which, shoutout to Scarlett Johansson.

8. Dick In A Box (with The Lonely Island)

Like Joey Tribbiani when he ate that chocolate cake, I’m not even sorry. Later Timberlake collaborations ‘Motherlover’ & ‘3-Way (The Golden Rule)’ run it close, but The Lonely Island’s debut single is the funniest song ever made. There’s really not much point elaborating any further. Just watch for yourself and try not to cry with laughter listening to Timberlake and Andy Samberg deliver the most ridiculous lyrics imaginable with a straight face.

7. Cry Me A River

Allegedly inspired by his break-up with Britney Spears- as any avid Top of the Pops magazine fans will remember- ‘Cry Me A River’ is the song that launched JT into a whole other stratosphere of popularity and is arguably the most definitive and instantly recognisable of his career. Setting a new benchmark for break-up songs and with an iconic video to match, 90’s babies like myself will forever hold this song close to their hearts. That ‘cry me a river’ is now a popular phrase in everyday lexicon is testament to the impact Timberlake has made on popular culture.

6. Lovestoned / I Think She Knows (Interlude)

Never mind the propulsive, beatbox-driven ‘LoveStoned’, ‘I Think She Knows’ could well be the greatest interlude of all-time. Like the moment the girl from an amazing night before leaves to get her taxi home, ‘I Think She Knows’ is an ethereal daydream from a whole other dimension. One of the true standouts on FutureSex/LoveSounds, this extraterrestrial two-parter captures the album theme better than any of the other tracks. The full repertoire of Timberlake’s skillset is on show: the elastic vocals, the lewd innuendos and the sweet balladry. Yet again, this song is best enjoyed with the innovative music video. Timberlake was truly at the top of his game in 2007, a master of event pop at a time before social media where boredom meant huddling round the TV and watching music videos all day. Remember that?

5. Mirrors

It takes a genius musician to craft an eight-minute track that is captivating from start to finish not just as a work of thought-provoking art but as a radio hit. Kanye West (‘Runaway’) and Frank Ocean (‘Pyramids’) are the only others that come to mind. As beautiful an ode to monogamy and the ’til death do us part’ ideal as a popstar has ever put to wax, ‘Mirrors’ is a familiar sentiment that will stand the test of time. What could’ve been a boring, saccharine ballad in lesser hands is in fact the most moving song of Timberlake’s career, with an equally compelling visual that traverses the life of a married couple through several decades. “So now I say goodbye to the old me, it’s already gone/And I can’t wait wait wait wait wait to get you home”. The Casanova that hypnotised every woman alive is long gone. The words “you are the love of my life’ never came across so sincere.

4. Like I Love You (feat. Clipse)

Rhythmically sophisticated yet instantaneously exciting, Justin Timberlake’s Clipse-featuring, Neptunes-produced debut single couldn’t have made his intentions more apparent: I’m not Mr *NSYNC anymore. Never before or since has a post-boyband single made such a splash. Screw the Man on The Woods faux-country aesthetic. Latin guitars and a Timberlake falsetto is a combo we need a lot more of. Any D.J. worth his salt will have three minutes and fifty-four seconds memorised as the most gorgeously mercurial keyboard ever broke down, which is why you’ll never hear it at Bot Wednesdays.

3. Señorita

Early Justin sang with such magnetism that when he delivered the now timeless call-and-response lyrics to the men and women in the crowd, each group took him as seriously as the other. Men wanted to be him and women wanted… well. ‘Señorita’ is a song guaranteed to galvanise the energy of any nightclub in the world. “Gentlemen, good night/Ladies, good morning/That’s it” is a suitably self-assured conclusion to a slinky, finger-snapping slow jam that never relents on its modus operandi: get people up and dancing. When Michael Jackson heard this song I bet he went straight to the studio.

2. Rock Your Body

“Bring the beat back.” It’s a video like this that makes Justin Timberlake’s case for Coolest Man Alive extremely formidable. Even when I’m 85, struck down with arthritis, back utterly fucked and widowed but taken along to a wedding by a long-lost friend just out of sympathy and sitting in the corner down-and-out, ready to die, if the DJ sticks this classic on I’ll be straight up and on to the dancefloor. Originally intended for Michael Jackson’s tenth album Invincible– other than ‘Break of Dawn’ it would’ve been the best song on there- ‘Rock Your Body’ was a song with retro sensibilities that was nevertheless of-the-moment. When your approach is faithful to the King of Pop your sound will never go out-of-date.

Which brings us to number one…

1. My Love (feat. T.I.)

Here we are, the best song of Justin Timberlake’s career. Like a tidal wave of sound, ‘My Love’ thumps and pulsates with equal measure. It has all the hallmarks of a stellar Timberlake track. There’s the dance ensemble music video, Timbaland’s stuttering bass synthesisers, the eccentric beatboxing, an imposing verse by T.I. in his prime and the best Timberlake chorus to date: “I can see us holdin’ hands/Walkin’ on the beach, our toes in the sand/I can see us on the countryside/Sittin’ in the grass, layin’ side by side/You can be my baby/Let me make you my lady, girl, you amaze me/Ain’t gotta do nothin’ crazy/See, all I want you to do is be my love.” Those lines come at a rapid pace yet everybody below the age of 30 can sing those lyrics. Why is that? It’s because deep down everybody wants to be the coolest person alive, and knowing all the words to ‘My Love’ is part of the gig. At the time of release, ‘My Love’ was ubiquitous. No wonder. ‘My Love’ is absolutely frenetic, a trailblazing and genre-blending tour de force that exponentially expanded the scope and ambition of what a mega-popstar could do with a single. For that reason, I deem ‘My Love’ to be the greatest Timberlake song of them all.