Jon Cryer

Jon Cryer is an American actor, screenwriter, film director, and film producer. Born into a show business family, Cryer made his motion picture debut as a teenaged photographer in the 1984 romantic comedy No Small Affair; his breakout role came in 1986, playing “Duckie” Dale in the John Hughes-written film Pretty in Pink. In 1998, he wrote and produced the independent film Went to Coney Island on a Mission from God… Be Back by Five.

Although Cryer gained fame with his early film roles, it took several years to find success on television; none of his star vehicles, including The Famous Teddy Z, Partners, and The Trouble with Normal, lasted more than 22 episodes. In 2003, Cryer was cast as Alan Harper on the CBS sitcom Two and a Half Men, for which he won two Primetime Emmy Awards in 2009 and 2012. 

Guest Appearances

March 24, 2024

Actor Jon Cryer joins Scott to talk about his new show Extended Family, appearing in the Mr. Show sketch “Monk Academy,” and his podcast Lawyers Guns and Money.

April 18, 2018

Actor Jon Cryer chats with Blake Harris about first commercial acting job at 4 years old, replacing Matthew Broderick in the Broadway plays Torch Song Trilogy & in Neil Simon’s Brighton Beach Memoirs, what lead him to play Lenny in Superman IV: The Quest for Peace, and the many other films he was in that he says could be discussed on HDTGM.

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March 9, 2017

Select highlights from Pardcast-a-thon 2017, a benefit for Smile Train, featuring Jon Cryer, Vance Gilbert, Sarah Silverman, and Kumail Nanjiani. Purchase the full 12-hour audio/video package at! Proceeds benefit Smile Train.

This episode is brought to you by Backblaze (www.backblaze/pardo).

May 5, 2016

Hiding out with Jon Cryer.

June 16, 2015

Join Kevin as he sits down with actor Jon Cryer (Pretty in Pink, Two and a Half Men) as Jon promotes his newly published memoir, So That Happened. Jon chats about growing up on Broadway, being a member of the Brat Pack, and life after Charlie Sheen.

April 10, 2015

Nate is excited to share his amazing interview with the one and only Jon Cryer. Jon recently released a new book called “So That Happened: A Memoir.” Jon talks about how writing a book came out of a dare, what he learned from working with Gene Hackman on Superman IV, his experience at Stagedoor Manor (an infamous summer camp for theater kids), the alternate ending to Pretty in Pink, and much more. Go get Jon’s book wherever books are sold or on Amazon: The book club episode is almost here, grab yourself the classic F. Scott Fitzgerald novel “Tender Is The Night” and send in your thoughts on the book at Make sure to come out to see the show LIVE on Sunday, April 12th at UCB-Franklin at 7:30pm. Get your tickets at!

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