Jon Cryer

Jonathan Niven Cryer was born on April 16, 1965, in New York City, into a family with deep roots in the performing arts. His mother, Gretchen Cryer, is a playwright, songwriter, actress, and singer, while his father, Donald David Cryer, is an actor and singer who originally trained for the ministry. His paternal grandfather, the Reverend Donald Walter Cryer, was a prominent Methodist minister. Cryer has two sisters, Robin and Shelly. He decided at age twelve that he wanted to pursue acting, attended Stagedoor Manor Performing Arts Training Center during several summers as a teenager, and graduated from the Bronx High School of Science in 1983, where he was a classmate of screenwriter and director Boaz Yakin. Rather than attend college, he enrolled in a summer Shakespeare course at the Royal Academy of Dramatic Art in London.

Cryer's professional career began on Broadway between 1982 and 1983. His first stage role was as David in the Broadway production of Torch Song Trilogy, in which he replaced Matthew Broderick, whom he closely resembled. He later reprised that role in productions in San Francisco and Los Angeles. He also served as a standby and replacement for Broderick in the role of Eugene Jerome in Neil Simon's Brighton Beach Memoirs during its original Broadway run.

At nineteen, Cryer made his film debut in the lead role of Charles Cummings in the 1984 romantic comedy No Small Affair, stepping in after the original production — which had also featured Broderick — was halted when director Martin Ritt suffered a heart attack. His breakout film role came in 1986 when he played Philip F. "Duckie" Dale in the John Hughes-scripted Pretty in Pink. The following year he starred in Hiding Out as a stockbroker evading a Mafia hit man, a performance that drew critical praise despite the film's modest commercial performance. Also in 1987, he appeared in Superman IV: The Quest for Peace as Lenny Luthor, nephew of the film's central villain, and had a lead role in Morgan Stewart's Coming Home. In 1991, he co-starred alongside Charlie Sheen in Jim Abrahams's comedy Hot Shots!, which was well received.

On television, Cryer took the lead role of Teddy Zakalokis on the CBS sitcom The Famous Teddy Z from 1989 to 1990, though the series was canceled after one season. He subsequently starred in the Fox sitcom Partners as Bob from 1995 to 1996, and in the Fox sitcom Getting Personal as Sam Wagner in 1998, which aired seventeen episodes before cancellation. In 1998 he also appeared in the film Holy Man and wrote, produced, and starred in the independent film Went to Coney Island on a Mission from God... Be Back by Five, which debuted at the Los Angeles Film Festival that year to positive critical notices. His role as Zack Mango on the ABC sitcom The Trouble with Normal in 2000 and 2001 marked yet another series canceled after its first season.

Cryer's career trajectory shifted significantly in 2003 when he was cast as Alan Harper on the CBS sitcom Two and a Half Men, a role he held until the series concluded in 2015. CBS executives had reservations about his casting given his prior string of canceled shows, but a friendship with co-star Charlie Sheen contributed to his selection. He earned seven Primetime Emmy Award nominations for the role and won twice: Outstanding Supporting Actor in a Comedy Series in 2009 and Outstanding Lead Actor in a Comedy Series in 2012. Following Sheen's departure from the series in 2011, Cryer's character became the show's central protagonist, with Ashton Kutcher joining as co-lead. Cryer is the only cast member to have appeared in every episode of the series. In 2011, he also received a star on the Hollywood Walk of Fame for Television. That same year he appeared as David in a concert staging of Stephen Sondheim's musical Company with the New York Philharmonic at Lincoln Center, in an all-star cast headed by Neil Patrick Harris and Patti LuPone; the concert subsequently aired on PBS's Great Performances.

In 2009, Cryer co-starred with James Spader in the film Shorts. From 2019 to 2021, he portrayed Lex Luthor on the CW series Supergirl and appeared in additional DC Comics-related television productions. He starred in the coming-of-age film Big Time Adolescence in 2019 and took the lead role of Jim Kearney on the NBC sitcom Extended Family from 2023 to 2024.