Justin Timberlake’s 23 Top 10 Singles (Including *NSYNC!): Revisited, Reviewed & Ranked
23. 50 Cent Featuring Justin Timberlake, “Ayo Technology” Year: 2007 Chart Peak: #5
This Timbaland-produced cut was a high-tech precursor to the sexting movement, as Fif and JT were both basically over using laptops and cellphones to have wildly interactive cyber sex (er, not with each other), and wanted the real thing. Who doesn’t, right?
In the video, Justin shows up on the doorstep of a woman he’s been very obviously Internet-banging to get the real thing. “Why don’t you sit down on top of me?” he asks repeatedly. Does he seal the deal? Watch it again to find out (Spoiler alert: Hello, of course he does). — KATHY IANDOLI
22. Gloria Estefan and *NSYNC, “Music Of My Heart” Year: 1999 Chart Peak: #2
It doesn’t get much more cloying than this diabetes-inducing, Diane Warren-penned movie ballad, which finds Gloria Estefan and *NSYNC trying to out-elevator Muzak each other. So of course it was a major worldwide hit.
Boring, but tastefully so — the TRL-topper that wouldn’t send Grandma into cardiac arrest if she wandered into the room at the wrong time (“Was that black nail polish…on a man?! Call 911!”) — “Music Of My Heart” at least earned Justin 1/6 of a Blockbuster Award for Best Pop Song In A Movie. That says it all, really. — JONATHAN RIGGS
21. *NSYNC, “(God Must Have Spent) A Little More Time On You” Year: 1999 Chart Peak: #8
Despite its unwieldy title (Jesus, take the parentheticals!), “(GMHS) ALMTOY” holds a special place in pop history as *NSYNC’s — and Justin’s — first Top 10 entry on the Billboard Hot 100.
Sure, it’s prettily sung and clever in an “oh, those were God’s footprints in the sand” kind of way, but unless you’re a long-denim-skirted mom who thinks the Hallmark store is too racy, it’s doubtful you’re cranking this (or the Alabama cover) in 2016. Praise Satan Justin’s songs got better after this treacle. — JONATHAN RIGGS
20. T.I. featuring Justin Timberlake, “Dead And Gone” Year: 2009 Chart Peak: #2
Tip nearly topped the chart (again) with his track about accepting evolution and everything that comes with it. However, strong praise is due to Justin for this one, as his hook zips through the cut with emotional intensity while he reflects on this crossroads in his life. The “Oh!” that marks the hook is a heavy one, followed by lyrics bidding adieu to his former self.
Sure, it feels like JT is also sending off a part of himself. (It was around this same time that Justin would make a hard pivot into both acting and behind-the-scenes music work, truly sealing his legacy as an icon.) But what he really did was help T.I. convey the message that it’s okay to say R.I.P. to the person you used to be. —KATHY IANDOLI