Jonathan Niven Cryer (born April 16, 1965) is an American actor. Born into a show business family, he made his film debut with a lead role in No Small Affair (1984); his breakout role was as Duckie in the John Hughes-written film Pretty in Pink (1986). Cryer then had lead roles in the films Morgan Stewart's Coming Home (1987) and Hiding Out (1987), starring roles in Superman IV: The Quest for Peace (1987) and Hot Shots! (1991), and the lead role of Teddy Zakalokis on the CBS sitcom The Famous Teddy Z (1989–1990).
In the late 1990s and 2000s, Cryer transitioned to television, with main roles as Bob on the Fox sitcom Partners (1995–1996), Sam Wagner on the Fox sitcom Getting Personal (1998), and Zack Mango on the ABC sitcom The Trouble with Normal (2000–2001). He also starred in the film Holy Man (1998), and wrote, produced, and starred in the independent film Went to Coney Island on a Mission from God... Be Back by Five (1998).
Cryer experienced a career resurgence when he was cast in a co-leading role as Alan Harper on the CBS sitcom Two and a Half Men (2003–2015), for which he won two Primetime Emmy Awards; Outstanding Supporting Actor in a Comedy Series in 2009 and Outstanding Lead Actor in a Comedy Series in 2012. He received a star on the Hollywood Walk of Fame for Television in 2011. Cryer also starred in the fantasy film Shorts (2009).
Post-Two and a Half Men, Cryer portrayed Lex Luthor on the CW television series Supergirl (2019–2021) and multiple other DC Comics-related shows. He had a lead role as Jim Kearney on the NBC sitcom Extended Family (2023–2024), and starred in the coming-of-age film Big Time Adolescence (2019).
Jonathan Niven Cryer was born on April 16, 1965 in New York City. His mother, Gretchen Cryer (née Kiger), is a playwright, songwriter, actress and singer. His father, Donald David Cryer, is an actor and singer who originally studied to be a minister. His paternal grandfather, the Rev. Donald Walter Cryer, was a prominent Methodist minister. He has two sisters, Robin and Shelly.
When Cryer was twelve years old, he decided he wanted to become an actor. When his mother heard this, she thought he should have a backup plan, and joked, "Plumbing is a pretty good career." Cryer attended Stagedoor Manor Performing Arts Training Center for several summers as a teenager, and is a 1983 graduate of the Bronx High School of Science. He was classmates with screenwriter and film director Boaz Yakin. 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.
Cryer's first professional acting effort was as David in the Broadway play Torch Song Trilogy, replacing Matthew Broderick, whom he "closely resembled." He reprised the role in San Francisco and Los Angeles. 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.
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. He went on to appear in small roles in films and television films.
Cryer made his film breakthrough as Philip F. "Duckie" Dale in the John Hughes-scripted film Pretty in Pink. 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.
Cryer then starred in the 1987 film Hiding Out as a stockbroker on the run from a Mafia hit man. His mother Gretchen played his aunt. The film broke even, but Cryer's performance as a character who was much older than him was critically acclaimed. In the same year, he played Lenny Luthor, nephew of supervillain Lex Luthor, in the film Superman IV: The Quest for Peace. In 1989, he got the lead role in the TV comedy series The Famous Teddy Z. His performance gained poor reviews and the show was canceled after the first season.
In 1990, Cryer appeared as Sandy in an Off-Broadway adaptation of Carnal Knowledge. That same year he appeared alongside future Two and a Half Men costar Charlie Sheen in the Jim Abrahams comedy Hot Shots!, which was received very positively. Cryer is frequently linked to the Brat Pack. 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. In 1993, he was asked to audition for the role of Chandler Bing on Friends, while doing a play in London. His reading was videotaped by a British casting agent but the tape failed to arrive in the U.S. before the network had made its final decision.
In 1995, Cryer was cast as Bob in the sitcom Partners, which, like his prior show The Famous Teddy Z, was canceled after its first season. In an interview with Time Out New York he stated, "Hey, every show I'm in goes down. Think about this: George Clooney was in 28 pilots, or something. It means nothing." 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. It debuted in 1998 at the Los Angeles Film Festival and gained positive reviews from critics. Leonard Maltin from Playboy Magazine called it "a breath of fresh air." That same year, Cryer landed in another TV series, the Fox sitcom Getting Personal, alongside Vivica A. Fox and Duane Martin. Although the show was picked up for a second season after its abbreviated spring run, it was canceled that fall, after airing 17 episodes in total.
In 1999, Cryer appeared as Neal in Jeffrey Sweet's play Bluff at the Victory Gardens Theater. In 2000, he was cast as the lead in a comedy series called The Trouble with Normal. For the third time, Cryer starred in a show which was canceled after its first season.
Cryer's long run of unsuccessful TV projects finally ended in 2003. 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. (He had auditioned for the role of Gaius Baltar on the Sci-Fi Channel's reimagined Battlestar Galactica at around the same time, but the role went to James Callis.) Cryer earned seven Primetime Emmy Awards nominations and two wins for his acting work on the show. In a comment on the show's high ratings, he said: "When you're on a show that's fighting for survival every week, you stop trusting your instincts, because you think, 'My instincts haven't worked so far.' But when people clearly like the show and are watching it in great numbers, it takes a huge amount of pressure off you. It allows you to trust your instincts and go with what has worked for you before."
After Sheen's departure from the series, Cryer's character became the show's protagonist (with Ashton Kutcher being cast as the co-lead) during the final four seasons. Cryer is the only actor to have appeared in every episode of the series; Sheen was fired in March 2011 and Cryer's on-screen son Angus T. Jones left the series at the end of season 10.
In 2008, Cryer appeared with Laurence Fishburne and James Cromwell in the film Tortured, and in 2009 co-starred with James Spader in the film Shorts.
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. The all-star cast was headed by Neil Patrick Harris and Patti LuPone. The concert subsequently aired on PBS's Great Performances.
Cryer made a guest appearance on the sitcom series Husbands in its second season. He was initially cast to voice the lead character in DisneyToon Studios' animated film Planes, a spin-off of Pixar's Cars franchise, but later dropped out and was replaced by Dane Cook. Cryer did however receive a credit on the film for "additional story material."