Anthony Michael Hall says he regrets turning down the lead role in 'Ferris Bueller's Day Off'

• Hall said John Hughes wrote the Ferris Bueller role specifically for him.
• The role went to Matthew Broderick when Hall passed due to a scheduling conflict.

Matthew Broderick crafted an iconic role playing the wise-cracking, fourth-wall-breaking high school title character in "Ferris Bueller's Day Off." But the role was originally supposed to go to Anthony Michael Hall and the actor is bummed he passed on it.

Back in the late 1980s, there was no hotter writer-director for young people than John Hughes, and Hall was like a son to him as the actor had become a star thanks to Hughes' movies like "Sixteen Candles" and "The Breakfast Club."

Hughes' plan was to have Hall be the lead in his next writing-directing effort, 1986's "Ferris Bueller's Day Off." Hall would play the lead, a high school senior who decides to skip school and go on an elaborate journey around downtown Chicago.

The problem was, Hall was busy.

"Hughes wrote 'Ferris' for me," Hall told Insider while promoting his new movie "Halloween Kills." "Because of the work he gave me, he gave me a career as a kid, I was busy with other work. So I wasn't able to do 'Ferris.'"

Instead, Hall starred in the forgettable action thriller "Out of Bounds" in 1986.

But that wasn't all. Hughes also wanted Hall to play Philip F. "Duckie" Dale in "Pretty in Pink." The rom-com classic came out the same year as "Ferris" (Hughes didn't direct "Pink" he only wrote the screenplay) and Hughes felt Hall was perfect as the geeky guy obsessed with Molly Ringwald's Andie Walsh character. But, again, he was too busy. The role went to Jon Cryer.

Hall said to this day, out of those two memorable 1980s roles, he regrets not taking Ferris Bueller the most.

"It would be Ferris because what I felt reading 'Pretty in Pink' was it felt like a reboot of 'Sixteen Candles,'" Hall said. "The girl wants the handsome kid and the dorky kid is after her. To me, it was replicating 'Sixteen Candles.'"

"But I thought there was a real uniqueness to Ferris," he continued. "I thought that would have been a lot of fun."

In fact, Hall felt Hughes was priming him for the Bueller role all the way back when he played the wise-cracking geek Ted in "Sixteen Candles."

"If you think back at 'Sixteen Candles,' that scene where I'm with the prom queen and I crash the Rolls-Royce and I break the fourth wall and I look into the camera? There's the basis for Ferris," he said. "We discovered him on set together. John would see that would work and that led to him creating a character like Ferris who is always breaking the fourth wall."

Sadly, Hall passing on Ferris Bueller and Duckie hurt Hughes so much that Hall said the two lost touch up until his death in 2009.

"It's one of the saddest things of my life because I loved the guy," Hall said of losing touch with Hughes. "He was a big brother to me. I spent a lot of personal time with him, I was like his third kid. Back in the day when we did those films I would hang out with him and his wife and two kids so I was their third son in a way. I had a real close relationship with John."

"He still was a teenager in some regards because he would take things very personal," Hall continued.

Hall has been working consistently in Hollywood since working with Hughes, but most recently he has found a successful second chapter in his career playing supporting roles in movies like "The Dark Knight," "Foxcatcher," and now "Halloween Kills."