Jon Cryer Makes His First Appearance on the Howard Stern Show

From Pretty in Pink to Two and A Half Men, Jon Cryer has had a pretty decorated career. In his 30-year career, Cryer had never done the Howard Stern SiriusXM show and that has now changed.

Cryer visited the sho to talk about his recent book "So That Happened: A Memoir," his early career and much more. Cryer began his interview with Stern revealing why he shaved his head.

Cryer said he was going bald and there was really no way around it so he just got rid of it.

Cryer sported the new do in an episode of Ashton Kutcher and Netflix's The Ranch. He joked that if he ever needed hair again he would just spot a toupee.

"Howard asked Jon when he started out people thought he was gay, even his wife. Jon said he isn't gay and he's not Jewish," according to MarksFriggin.

"He said people thought he was republican too. He said he went to a John McCain fund raiser years ago and apparently that makes you republican."

Cryer told Stern that Molly Ringwald didn't think he was until he was casted as Duckie in Pretty In Pink. He also revealed that Robert Downey Jr. was also in talks for the role.

"Howard said Jon's mom was a playwright and actress. Jon said she wrote a play that ran for 3 years on Broadway. Howard said his dad ran off when Jon was only 4," according to Mf.

"Jon said a lot of actors get to a certain phase in their life and they have to try movies after doing plays.

He said he got some parts in movies but it wasn't enough to sustain. He said he had 2 more kids and he couldn't sustain two families."

Cryer said he had no resentment towards his dad when he returned to the family later on in his life. Stern and Cryer got to chatting about the book and how Cryer addressed the fact that he was often mistaken for Matthew Broderick.

He started out in the business at age 4 and his mother saved his money and put it into a college fund for him.

He also told Stern that he went to an acting camp where Robert Downey Jr., Zach Braff and Natalie Portman came out of.

Later on in the interview Cryer was open about his finances prior to his role in Two and A Half Men. He told the Stern Show crew and listeners that things had gotten bad before the show.

Cryer had been laying low for a while and was in talks for plenty of roles that fell through.

He even revealed that he auditioned for a role in Friends. The entire interview was pretty extensive as you would expect for his first time appearing on the Stern Show, the full transcript can be read here.