Jon Cryer is making his way up in the Luthor family.

The longtime actor, who memorably played Lex Luthor’s nephew Lenny in the final Christopher Reeve Superman movie, 1987’s Superman IV: The Quest for Peace, has just been cast as Lex Luthor himself on The CW’s Supergirl. In taking on the much anticipated role, he’ll be the latest in a long line of acclaimed actors to play the infamous DC super-villain.

Photo by Matt Beard

“We are enormous fans of Jon Cryer, and he was instantly our dream actor to play the iconic role of Lex Luthor,” said Supergirl Executive Producers Robert Rovner and Jessica Queller. “Jon is a super-talent, and the fact that he played Lenny Luthor in Superman IV brings an added layer of legacy to his casting. We’re beyond thrilled to welcome Jon to the Supergirl family.”

Cryer was early in his acting career when he appeared in Superman IV, having previously won over a generation of fans with his beloved role as Duckie in John Hughes’ Pretty in Pink. He’s since gone on to have a long career on both the big and small screen, appearing in movies and TV shows like Hot Shots!, The Famous Teddy Z , Getting Personal and most recently, Two and a Half Men. The internationally popular sitcom ran for a total of twelve seasons and yielded Cryer two Emmy Awards for his role as Alan Harper. Yet, while Two and a Half Men may be what Cryer is most well-known for these days, he’s no stranger to playing DC villains. While Lenny Luthor is probably Cryer’s most famous DC role—at least, until now—it’s not his only one. He’s also voiced the character of Felix Faust numerous times on Cartoon Network’s Justice League Action.

Thanks to his longtime association with the Man of Steel, Lex Luthor is one of the most widely known comic book villains in the world. Debuting two years after Superman in 1940’s ACTION COMICS #23, Lex would continue to play a key role in both Superman’s world and the DC Universe ever since. Loathing Superman for displacing Lex’s role as the savior of mankind and viewing the mega-powered Man of Steel as a threat to humanity’s existence, Luthor has been a thorn in Superman’s side in comics, movies, TV, games and books. On the screen, he was memorably played by legendary actor Gene Hackman in Superman, Superman II and Superman IV, as well as John Shea in Lois & Clark, Michael Rosenbaum on Smallville, Clancy Brown in Superman: The Animated Series, Jesse Eisenberg in Batman v Superman: Dawn of Justice and most recently, by Rainn Wilson in The Death of Superman.

Luthor was first announced as appearing on Supergirl last month. He’ll be seen alongside series regular Katie McGrath as Lex’s sister, Lena Luthor, and Brenda Strong as his mother, Lillian. Lex will be a recurring role on Supergirl, and Cryer will make his debut in the show’s 15^th episode this season.

So, what do you think, Super-friends? Did you ever think you’d see Lex Luthor on Supergirl? Did you ever think you’d see Jon Cryer as Lex Luthor on Supergirl? Let us know in the comments below!