Jon Cryer: Movies & Box Office

Jonathan Niven Cryer, known professionally as Jon Cryer, was born on April 16, 1965 in New York City to a family steeped in entertainment. His mother, Gretchen Cryer, is a playwright, songwriter, actress, and singer, while his father, David Cryer, is an actor and singer with a background in ministry. Raised with two sisters, Robin and Shelly, Jon decided at age twelve to pursue acting, a decision encouraged by his mother’s insistence on a backup plan—plumbing. He attended the Bronx High School of Science, spent summers at Stagedoor Manor, and later studied a short Shakespeare course at the Royal Academy of Dramatic Art in London, skipping college to follow his passion. Cryer’s early career began on Broadway, where he replaced Matthew Broderick in Torch Song Trilogy and later served as a standby in Brighton Beach Memoirs. At nineteen he landed his first film lead in No Small Affair (1984) and achieved breakout fame as the lovable, eccentric “Duckie” in John Hughes’s Pretty in Pink (1986), a role that cemented his status as a cult‑iconic figure of the 1980s. Throughout the late 1980s and 1990s he starred in a series of films—including Superman IV: The Quest for Peace, Hot Shots!—and headlined several short‑lived sitcoms such as The Famous Teddy Z and Partners, earning a reputation for being cast in shows that struggled to survive. The turning point arrived in 2003 when he was cast as Alan Harper on the hit sitcom Two and a Half Men. Cryer’s nuanced performance earned him two Primetime Emmy Awards (2009, 2012) and a star on the Hollywood Walk of Fame in 2011. After the series ended, he continued to diversify his portfolio with roles like Lex Luthor on Supergirl (2019‑2021), a guest spot on NCIS, and a lead in the coming‑of‑age film Big Time Adolescence (2019). Outside of acting, Cryer authored the memoir So That Happened (2015), participates in podcasts such as Undisclosed, and remains active in industry labor movements, supporting both the 2023 Writers Guild and SAG‑AFTRA strikes. His personal life includes marriages to British actress Sarah Trigger (1999‑2004) with whom he has a son, Charlie Austin, and to entertainment reporter Lisa Joyner (married 2007) with whom he adopts a daughter, reflecting a family life grounded in both creativity and resilience.