Rise to Fame
Duckie Dale was never supposed to be the loser. Pretty in Pink's original ending had Andie choosing him over Blane, but test audiences killed the romance and the studio reshot the finale. Cryer was blindsided. He'd played the whole performance like Duckie was the real lead. Molly Ringwald had pushed for Robert Downey Jr., and Anthony Michael Hall passed to dodge typecasting. Cryer got a genuinely good character, lost the girl anyway, and still became the face people remember from that film.
In the Spotlight
Charlie Sheen called him 'a turncoat, a traitor, a troll' after getting fired from Two and a Half Men in 2011. Cryer's public reply was a sardonic Conan O'Brien quip ('The fact is, I am a troll') and nothing more. He stayed on the show and walked away with two Emmys for the same character (supporting in 2009, lead in 2012). That double is rare in TV. His salary hit roughly $550,000 per episode mid-run. His NBC sitcom Extended Family wrapped in 2025, and he's publicly killed any reboot talk, managing the rare trick of escaping a Charlie Sheen story with his reputation intact.
Side Notes
He went to junior high with Robert Downey Jr., and Molly Ringwald later lobbied to cast RDJ as Duckie, the role that made Cryer famous. His 1993 audition tape for Chandler Bing got lost in transit from London. He played Lex Luthor across four DC shows. His mother played his aunt in Hiding Out. His two front teeth are fake, knocked out when he dove into the shallow end of a pool. The career he didn't have is almost as interesting as the one he did.