Cemented forever in the minds of teenage girls as the lovelorn Phil "Duckie" Dale in "Pretty in Pink" (1986), actor and writer Jon Cryer would years later attain a mature kind of fame as uptight Alan Harper on the hit sitcom, "Two and a Half Men" (CBS, 2003-15). In between those career-defining projects, Cryer had a number of wide-ranging roles, playing supervillain Lenny Luther in "Superman IV: The Quest for Peace" (1987) and a Wall Street broker avoiding the mob in "Hiding Out" (1987). After starring as the titular character on the short-lived cult series "The Famous Teddy Z" (CBS, 1989-1990), he first crossed paths with future "Two and a Half Men" co-star Charlie Sheen on the spoof comedy "Hot Shots!" (1991). Meanwhile, Cryer continued a professional collaboration with Jennifer Tilly by appearing opposite her in the caper comedy "Heads" (1993), before co-starring with the actress in his screenwriting debut, "The Pompatus of Love" (1995). After wending his way through a number of lower-profile features and several guest starring stints on the small screen, Cryer elevated his status when he joined "Two and a Half Men," a raunchy comedy that turned into a huge ratings winner for CBS, even though it suffered from the unpredictable behavior of star Sheen. Still, Cryer was able to weather that particular storm - and win an Emmy for his sitcom work in 2012 - while managing to escape the confines of being identified solely as the goofy and eccentric "Duckie."