"As far as red heads, you're nowhere near best. You're not Julianne Moore, you're Julianne Less," Cryer spits at Ringwald on the TBS series.
After Cryer suggested Ringwald get herself "50 more candles," Ringwald said Cryer had "a lot of emotion for Charlie Sheen's side piece" and roasted them both for having been replaced by Ashton Kutcher, who went on to marry Demi Moore.
Cryer then came for Ringwald's musical skills -- or lack thereof -- saying her 2013 jazz album made the genre "more boring than it seems."
"As far as red heads, you're nowhere near best. You're not Julianne Moore, you're Julianne Less," Cryer fired at Ringwald. "Molly's a ginger and creepy as shit. You woulda been great as Pennywise, the clown from 'It.'"
Ringwald retaliated by asking Cryer if he was "the half man in 'Two and a Half Men'" before shaming his skills in bed.
Of course there were lots of references to their classic teen comedy, in which Cryer played Ringwald's BFF, Duckie. "You cradle-blade loser, we loved every minute, I invented the friend zone just to put you in it," Ringwald said. "You're such a great actor, we believed every word, but the lines are blurred when you're actually a nerd."
"I got two Emmys and ridiculous clout, you got an awkward teen phase, and then never got out," Cryer fired back before making his own "Pretty in Pink" reference: "So this is the moment it all hits you, when Andie picked Blane, she picked the wrong dude."
Ringwald's retort: "You think Andie picked wrong? Well, listen to this: You're ugly and grey, dude, I'm pretty in pink."
Ringwald and Cryer were both bonafide '80s stars, and haven't stopped acting since. Coincidentally, both of their IMDb profiles reflect 63 total acting credits. These days, Ringwald plays Archie's mom on "Riverdale." After Cryer finished up his long run as Alan Harper on "Two and a Half Men," he went on to play himself on "Ryan Hansen Solves Crimes on Television," book a recurring role on "NCIS" and voices a character on animated series "Justice League Action."