Since shedding his boy band image (R.I.P. *NSYNC), Justin Timberlake has flourished as a pop powerhouse since releasing his solo debut, 2002’s Justified.
His blue-eyed soul has helped him land repeat-worthy collaborations with some of hip-hop and R&B’s finest along the way, including the likes of production heavyweight Timbaland and rap icon Jay Z. Even his breakout solo hit “Like I Love You” featured a guest verse from Virginia-bred duo Clipse.
These days, Timberlake is relishing in fatherhood and keeping the world on its feet with the Golden Globe-winning single “Can’t Stop The Feeling” off the soundtrack for the DreamWorks film Trolls. While a highly anticipated follow-up to 2013’s two-part The 20/20 Experience in the new year is still TBD, revisit J.T.’s best rap and R&B duets below.
Justin Timberlake, “Like I Love You” Feat. Clipse (2002)
Back when Timberlake was a baby-faced bachelor, this groovy number cemented J.T.’s solo career as a genre-fusing wunderkind. Featuring production from The Neptunes (Chad Hugo and Pharrell Williams) and a special sixteen from Clipse (Pusha T and then-named Malice), the lead single off Justified was a dancefloor magnet.
The Black Eyed Peas, “Where Is The Love?” (2003)
While Timberlake offers his signature vocals to the hook, this B.E.P. track peaked at No. 8 on the Hot 100 and served as an anti-gun violence anthem. Originally released in 2003, the group’s members apl.de.ap, Taboo, will.i.am and Fergie released a 2016 version of the track which included Jamie Foxx, Ty Dolla $ign, Mary J. Blige, Justin Timberlake and Jaden Smith.
Snoop Dogg, “Signs” Feat. Justin Timberlake & Charlie Wilson (2004)
The D-O-double-G recruited J.T. and Charlie Wilson for this R&G (Rhythm & Gangsta): The Masterpiece single, produced by The Neptunes. Timbelake glides on the hook, singing about a potential bae, “I’m not sure what I see/Cupid don’t f–k wit me!/Are you telling me this is a sign?/She’s looking in my eyes, now I see no other guys/Are you telling me this is a sign?” “Signs” also hit the Hot 100, reaching No. 46.
50 Cent, “Ayo Technology” Feat. Justin Timberlake (2007)
This 50 Cent collaboration hit No. 5 on the Hot 100 in 2007, featuring a very direct come-on line from Timberlake who utters on the chorus, “Ayo, I’m tired of using technology/Why don’t you sit down on top of me?”
Justin Timberlake, “SexyBack” Feat. Timbaland (2006)
To kick off his new wave R&B sound on his 2006 sophomore set FutureSex/LoveSounds, Timberlake tapped his partner-in-crime Timbaland for the sexy single, which was inspired by David Bowie‘s Diamond Dogs and The Rise And Fall of Ziggy Stardust and the Spiders From Mars.
Justin Timberlake, “My Love” Feat. T.I. (2006)
Timberlake teamed with Tip for the FutureSex set’s second single, which also nabbed the 2007 Grammy for Best Rap/Sung Collaboration.
Justin Timberlake, “Chop Me Up” Feat. Three 6 Mafia & Timbaland (2006)
Timberlake and Three 6 Mafia (mainly DJ Paul and Juicy J) represented their Tennessee roots with this hard-hitting, chopped and screwed cut from FutureSex/LoveSounds.
Justin Timberlake, “Until The End of Time” Feat. Beyonce (2006)
Though initially released with Timberlake as the lone artist, this dreamy love song off FutureSex/LoveSongs landed a remix from Beyonce and also helped the headliner become the first solo male artist of that decade to release six top 40 hits from the same album.
Rihanna, “Rehab” Feat. Justin Timberlake (2007)
On the bad gal’s third studio effort Good Girl Gone Bad, Rihanna called on Timberlake for an assist on this Hannon Lane and Timbaland-produced entry about a crumbling relationship. Timberlake also appeared in the dark, steamy video.
The Lonely Island, “Dick in a Box” Feat. Justin TImberlake (2008)
This Saturday Night Live digital short spawned a full-length version that helped the comedic trio (Akiva Schaffer, Andy Samberg, and Jorma Taccone) win an Emmy for “Best Original Music and Lyrics” in 2007. Donning oversized suits and gift-wrapped boxes on their crotches, J.T. and Samberg sing of giving their special women a, er, simple gift.
Ciara, “Love Sex Magic” Feat. Justin Timberlake (2009)
Off Ciara’s 2009 set Fantasy Ride, “Love Sex Magic” finds the pair oozing chemistry, especially in the eye-popping visual that finds CiCi flaunting her flexibility in front of a receptive Timberlake.
Justin Timberlake, “Suit & Tie” Feat. Jay Z (2013)
Giving new swag to business attire, J.T. and close pal Jay Z clink their champagne glasses for this dapper number, which served as Timberlake’s comeback single off The 20/20 Experience.
Justin Timberlake, “Cabaret” Feat. Drake (2013)
Part 2 of the 20/20 double-album release featured a J.T. collaboration with Drake for the frisky “Cabaret,” where the self-proclaimed 6 God lays down a verse fit for a nightclub rendezvous.
Jay Z, “Holy Grail” Feat. Justin Timberlake (2013)
Jay Z and J.T. linked back up for the lead single off the Brooklyn rapper’s 2013 effort Magna Carta Holy Grail, which features Timberlake’s vocals in raw, heart-wrenching form as he sings of the pitfalls of fame.