6. “Dick in a Box”
Sure, this horny-yet-hysterical collaboration with comedy troupe Lonely Island was the first hint of Timberlake’s funny bone. But let’s be real: This viral hit that debuted on SNL back in 2006 has only given folks an out when they dropped the ball — err, box — with unimaginative gifting. A whole generation of disappointed romantics have J.T. to thank for the strategically placed cut-out gift box they’ve received on at least one occasion.
5. All that damn rapping with Jimmy Fallon
Not to go all “hip-hop is Black art” on you, but if White people are gonna do it, they need to be out-of-this-world talented — you know, gotta work twice as hard! — or at the very least make it seem effortless. This multipart “History of Rap” bit with Jimmy Fallon was… not quite that. Somewhere, Kool Herc is crying.
4. 'The 20/20 Experience — 2 of 2'
After a seven-year drought following his classic FutureSex/LoveSounds album, J.T. dropped a smooth, fun, and cool comeback LP with The 20/20 Experience, another stellar full-length linkup with Timbaland. He damn near brought sexy back again. But then, a few months later, he dropped this dreadful cash grab of a sequel. The album put a stain on its predecessor, thanks to questionable concepts (vampirism?) and lukecold outtakes that no one asked for.
3. 'Out of Time'
The same could be said for numerous women in Justin Timberlake’s life, but Amanda Seyfried didn’t deserve this!
2. N*SYNC-era hair
The sheer volume of gel needed in this Top Ramen-channeling hairstyle is probably responsible for, like, 2% of all landfill dumps in the world. The. World.
1. 'Man of the Woods'
The marketing plan and content around this Johnny Appleseed headassery of an album was J.T.’s sharp pivot toward musical Whiteness. When Black folks are saying, “Yo, it was better when you were tryna be Black,” you know you’ve hit your ceiling. Stick to appropriating, colonizer!