Jon Cryer is the son of Gretchen Cryer, a playwright, songwriter, actress, and singer, and David Cryer, an actor, singer, and producer. When Cryer was 12 years old he decided that 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.

At age nineteen Cryer first appeared in the 1984 romantic comedy film No Small Affair, having the lead role as Charles Cummings. He went on to having small roles in films and television movies, but he made his breakthrough when he was cast to portray Phil "Duckie" Dale in the John Hughes film Pretty in Pink. Thanks to Pretty in Pink Cryer slowly became more famous. In 1987 he portrayed Superman villain Lenny Luthor in Superman IV: The Quest for Peace. In 1989, Cryer got the lead role in the TV comedy series The Famous Teddy Z. His performance gained poor reviews and the series was canceled after the first season.

One year later, Cryer starred with Charlie Sheenin the Jim Abrahams comedy Hot Shots, which was received very positively. Cryer was asked to audition for the role of Chandler Bing on Friends, while he was 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 to portray Bob in the sitcom Partners, which, like Cryer's prior show The Famous Teddy Z, was canceled after its first season. After guest starring on shows like Dharma & Greg and The Outer Limits, Cryer successfully wrote and produced his first film Went to Coney Island on a Mission from God... Be Back by Five, it debuted in 1998 at the L. A. Independent Film Festival and gained positive reviews. In 2000, Cryer, again, got the lead in a comedy series, it was called The Trouble with Normal; for the third time, a show in which Cryer starred got canceled after its first season.

Cryer's unsuccessful track record with TV finally came to a stop three years later. Against the wishes of CBS executives aware of his past failures, in 2003 he was cast to portray Alan Harper on the hit comedy series Two and a Half Men, for which he has earned three Primetime Emmy Award nominations.