Cryer kicked things off dissing Ringwald's recent acting roles, as he rapped, "You guest star on 'Riverdale,' that made me pause. Do you play one of the high schooler's great-grandmas? In a movie you rejected me to be your boyfriend. But tonight is the night Duckie gets his revenge," while Ringwald threw shade at the fact that Cryer used to date actress Demi Moore before Moore famously dated Ashton Kutcher. "With Demi Moore, I'm shocked that she'd date you. Hey, you and Charlie both had Ashton replace you," rapped Ringwald.
Cryer clapped back by pulling the age card multiple times, even though he's actually older than Ringwald. "You're a cautionary tale of an actress-turned-cougar. Sophie Turner, look, it's the Ghost of Christmas Future. I've got two Emmys and ridiculous clout. You got an awkward teen phase and then never got out," rapped Cryer. He continued, "So this is the moment it all hits you. That when Andie picked Blane, she picked the wrong dude."
But, in the end, the crowd went wild for Ringwald, who took home the trophy when she easily dropped the mic. "When you're on the screen, you eat up every scene. How the hell'd you come out. Looking worse than Charlie Sheen? As a cover, it's hot, you were on 'TV Guide.' Man, you're so past tense, they should call you Johnny Cried. You think Andie picked wrong? Well, listen to this. You're ugly in gray, dude, I'm pretty in pink, bitch!"