Jon Cryer knows how to play the long game. After breaking out in Pretty in Pink, starring as the lovelorn outsider Duckie alongside Molly Ringwald's Andie, he appeared in plenty of TV shows and films. But for many years, none resonated the way his classic 1986 teen romance did. But in 2003 the hit sitcom Two and a Half Men put him back in the center of the zeitgeist and earned him a pair of Emmys over its 12-year run. "The right projects come along at the right times. You can't force things," says Cryer, now 58.
"You just have to be patient." The New York City native, who shares son Charlie, 23, with ex Sarah Trigger and Daisy, 4, with wife Lisa Joyner, is now starring on NBC's Extended Family, a comedy about
an amicably divorced couple navigating family life as the wife (Abigail Spencer) moves on with a new flame (Donald Faison). It's a scenario that reminded Cryer of his own family dynamic: After his screenwriter mother and his actor father split up, his mom forged a tight friendship with his stepmother. "I think that kind of closeness is achievable and can be great," says Cryer. He shared more life lessons with People.
Show business is not fair.
My mother was a successful playwright by the time I got Pretty in Pink. I remember the day her musical I'm Getting My Act Together and Taking It on the Road opened Off-Broadway [in 1978]. The reviews came out, and they were largely scathing.
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