Born into a show business family, he made his motion picture debut as a teenage photographer in the romantic comedy No Small Affair (1984); his breakout role was as Duckie in the John Hughes-written film Pretty in Pink (1986).

In 2003, he was cast in a co-leading role as Alan Harper on the CBS sitcom Two and a Half Men, which became a major hit for twelve seasons, and for which he won two Primetime Emmy Awards (in 2009 and 2012).

"[10] Cryer attended Stagedoor Manor Performing Arts Training Center for several summers as a teenager,[12] and is a 1983 graduate of the Bronx High School of Science.

[13] To his mother's "great disappointment," he skipped college and went to the Royal Academy of Dramatic Art in London, England, for a summer short course in Shakespeare.

[14] Cryer's first professional acting effort was as David in the Broadway play Torch Song Trilogy, replacing Matthew Broderick, whom he "closely resembled.

[16] He was later a standby and replacement for Broderick as Eugene Jerome in the original Broadway production of Neil Simon's Brighton Beach Memoirs in 1984.

[16][citation needed] At age 19, Cryer appeared in the 1984 romantic comedy film No Small Affair, in the lead role as Charles Cummings, after the original production with Matthew Broderick was shut down when director Martin Ritt suffered a heart attack.

[18] In an interview with the Daily News, Cryer's mother Gretchen said that after Pretty in Pink, she started getting calls from teenage girls from all over the world, who would leave hysterical, giggling messages on her answering machine.

[20] That same year he appeared alongside future Two and a Half Men costar Charlie Sheen in the Jim Abrahams comedy Hot Shots!,[11] which was received very positively.

[22] In a March 2009 interview on Anytime with Bob Kushell, Cryer stated that he had auditioned for St. Elmo's Fire but was not cast in a role.

"[10] After guest starring on shows such as Dharma & Greg and The Outer Limits, he wrote, produced and co-starred in the film Went to Coney Island on a Mission from God... Be Back by Five.

Against the wishes of CBS executives (who were aware of his past failures) and due to a friendship with Charlie Sheen, he was cast as Alan Harper on the hit comedy series Two and a Half Men.

"[11] After Sheen's departure from the series, Cryer's character became the show's main protagonist (with Ashton Kutcher being cast as the co-lead) during the final four seasons.

[32] In 2011, Cryer played the role of David in a concert staging of Stephen Sondheim's musical Company with the New York Philharmonic at Lincoln Center.

[35] He was initially cast to voice the lead character in DisneyToon Studios' animated film Planes, a spin-off of Pixar's Cars franchise,[36] but later dropped out and was replaced by Dane Cook.

[41] Pursuing a passion for criminal justice, Cryer joined the team of the popular podcast Undisclosed where he will be voicing the weekly addendum episode for the second season.

Cryer uncovered the dramatic tale of his ancestor James Adams, a Scottish Covenanter soldier who was captured during the Battle of Dunbar in 1650, and endured horrific conditions as a prisoner.

"[citation needed] On November 16, 2018, it was announced that Cryer had been cast as Lex Luthor on The CW's Supergirl in a recurring role.

On a February 2007 episode of The Tonight Show with Jay Leno, he announced that he was engaged to entertainment reporter Lisa Joyner, whom he married in Mexico[10] in June 2007.

"[52] Cryer was asked in 2014 if he was "mistaken for gay"; he called himself "an effeminate heterosexual dork" and made a tongue-in-cheek remark about never being propositioned: "Fellas, you're dropping the ball.

"[56] In fact, Federal Election Commission reports show that Cryer donated the maximum legal amount to the Obama campaign in August of 2008[1].