MTV prides itself on letting celebrities (A-list and B-list alike!) do and say as they please on the network’s annual Video Music Awards jamboree. This has made for more than a few memorable pop culture moments over the years. It’s also given rise to ample opportunities for jokes to fall flat, head-scratching performances, and cameras to catch horribly uninterested looks from unsuspecting audience members. Ah, awkwardness. It wouldn’t be the VMAs without it. To gear up for tomorrow’s 29th installment, we take a look in the YouTube vault and shine a light on some of the show’s most magical ill-at-ease moments.