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4 Fascinating Anecdotes From Jon Cryer's "Wry, Funny, and Self-Deprecating Memoir"

Jon Cryer opened up about cancer, Demi Moore, and movie sets in his 2015 memoir, So That Happened

By Jax Miller

The talented Jon Cryer is bringing the laughs to NBC’s upcoming sitcom, Extended Family, but there’s a lot you might not know about Cryer. That's what makes his memoir such a delightful read: It's filled with both fascinating anecdotes and thoughtful reflections.

How to Watch

Watch Extended Family Tuesdays at 8:30/7:30c on NBC and next day on Peacock.

In 2015, the Emmy Award-winning actor, just off his uber-successful run on Two and a Half Men, penned So That Happened, a memoir published by Penguin Random House’s Berkley Books. According to the publisher’s blurb, Cryer covered much between his 1986 Hollywood breakthrough role as Duckie in Pretty in Pink to his time alongside Charlie Sheen in Two and a Half Men, which earned a whopping 46 Primetime Emmy nominations during its 12 years.

In his “revealing, humorous, and introspective” book, Cryer recounts his decades in Hollywood, including his brushes with some big-hitter names, including Robert Altman, Christopher Reeve, and fellow Brat Packer Judd Nelson.

“With the instincts of a natural storyteller, Cryer charts his extraordinary journey in show business, illuminating his many triumphs and some missteps along the way,” wrote Berkley. “Filled with exclusive behind-the-scenes anecdotes, Cryer offers his own endearing perspective on Hollywood, the business at large, and the art of acting.”

Here are just some of the more shocking reveals to be learned from So That Happened:

Jon Cryer Had a Rare Cancer (Twice)

At just 24 years old, Cryer learned he had what he called “a very minor, rare, weird form of cancer, a lump that attaches to the underside of one’s skin,” per his memoir. Namely, Cryer had dermatofibrosarcoma protuberans, a type of cancer formed in the connective tissue of the dermis and widely believed to be caused by a genetic mutation.

Thankfully, the cancer is easily treatable if found early, which was the case for Cryer, who’d just found success on the big screen.

Jon Cryer smiles on the red carpet for the premiere of Big Time Adolescence

In 2022, Cryer spoke with the HypochondriActor podcast to discuss the “little spot” he had on his sternum that wouldn’t grow hair. He visited a doctor, who admitted to Cryer that he didn’t know what the growth was, leaving Cryer with the decision about whether he wanted it removed.

Cryer had an outpatient surgical procedure and, despite being advised to take it easy, he participated in a “strenuous” activity with a long-time crush, causing the wound to burst and trigger an emergency trip to the hospital, he said in the light-hearted conversation.

He joked that he found the lump in an area where he was trained (as an actor) to channel his negative emotions, calling the tumor “shame cancer.”

RELATED: Jon Cryer Returns to TV: Why He Said Yes to NBC’s “Incredibly Unusual” Sitcom Extended Family

“You’re 24; you have no concept that this is something that is really terrifying,” said Cryer.

Cryer explained the cancer returned at age 35, giving him “a much different” experience, especially since he’d become a father.

“It’s very weird; there’s no history of it in my family, that I’m aware of,” he told the podcast. “I don’t know where it came from.”

Research shows that dermatofibrosarcoma protuberans affects only about 1,000 people per year in the United States, though it is twice as prevalent in the African-American community, according to the American Society For MOHS Surgery.

Thankfully, Cryer has made a full recovery.

Demi Moore and Jon Cryer's Relationship

In So That Happened, Cryer discussed the “inaugural Hollywood romance” between him and Demi Moore when both were still budding actors in the 1980s, something Moore also addressed in her 2019 memoir, Inside Out.

Cryer and Moore both appeared in the 1984 film No Small Affair, where Cryer starred as a teenage photographer who falls in love with one of his subjects, a nightclub singer played by Moore.

“I discovered that on top of her sex appeal and openness, she was an absolute goofball, which I quickly learned is a devastatingly attractive combination to me,” Cryer wrote in his memoir.

The resulting sexual engagement was discussed years later when Moore mistakenly lamented taking Cryer’s virginity. She called herself “callous” for stealing “what could have been such an important and beautiful moment from him.”

Jon Cryer smiles during the Password Season 1 Holiday Special

But what made this statement funny to Cryer was that he wasn’t a virgin when he and Moore hooked up, as published on X, the social media platform formerly known as Twitter.

“Well, the good thing about this is she doesn’t have to feel bad about it anymore because while I’m sure she was totally justified [in] making that assumption based on my skill level (and the stunned look on my face at the time), I had actually lost my virginity in high school,” posted Cryer, according to PEOPlE

Cryer added, “But she’s right about the other part; I was over the moon for her during a very troubled time in her life. I have nothing but affection for her and not a regret in the world.”

Flash forward to almost 30 years later, when Moore’s then-husband, Ashton Kutcher, replaced Charlie Sheen as Cryer’s costar in Two and a Half Men, as Cryer described in his book.  “At this time, Ashton was sporting his expanding kabbalah beard, but what he also had was a wife I had dates [with] when he was 7 years old.”

Cryer recalled his first-time meeting with Kutcher as being “very awkward” when speaking with E! News, though it appeared all was fine since Moore had already let Kutcher know and told him not to “feel weird” about it.

Both co-starred together on Two and a Half Men from seasons 9 to 12.

Jon Cryer's Time on Pretty in Pink

In the days of the Brat Pack and all their big hair glory, Cryer played the unforgettable Duckie in the era-defining 1986 teen romance Pretty in Pink. Cryer added color to the film as a high schooler too afraid to confess his feelings of love for his BFF, played by Molly Ringwald.

However, despite the on-screen chemistry between Cryer, Ringwald, and actor Andrew McCarthy, things weren’t great when the cameras stopped rolling, as Cryer explained in his memoir.

“Molly would meet my verbal parries with awkward silences,” he said of Ringwald. Of McCarthy, Cryer added, “Trying to befriend Andrew was so tough, it sent me in the other direction: as in, I adopted a low-boil dislike for him.”

But the cast, including Annie Potts, seemed to get along well when reuniting in 2010.

At the time, Ringwald commented about Duckie being the stereotypical gay best friend in the film. Despite Duckie being referenced as “a gay icon,” Cryer said, he “never quite saw him that way,” going further into detail about his character in the memoir.

“Saying Duckie was gay, frankly, is a kind of cop-out, too easily a sexuality tag in this label-busting era for gender roles, too easy an explanation for an outsider losing the girl, and suggests that nobody that flamboyant could possibly be straight,” Cryer wrote. “I respectfully differ on that one, Molly.”

While on the set of Pretty in Pink, Cryer also formed a bond with actor (and former Brat Packer) James Spader, star of NBC’s crime series The Blacklist.

Jon Cryer's Time on Two and a Half Men

Many had questions surrounding Cryer and his Two and a Half Men costar, Charlie Sheen, especially after Sheen suffered what’s been referred to as a public meltdown in 2011, leading to Sheen’s unceremonious departure from the series.

But the pair met years before the show's 2003 premiere, as both had roles in the 1991 comedy Hot Shots!, a parody of the successful '80s flick Top Gun. In his memoir, Cryer dove into the way things changed while working on Two and a Half Men. He also opened up about how he and other staff members, including the show's creator Chuck Lorre, tried to get Sheen back on the straight and narrow.

While Cryer and Sheen had their ups and downs, as detailed in the memoir, Cryer still apparently has positive feelings for Sheen (on December 7, 2023, Sheen told PEOPLE he was just one month shy of celebrating six years sober).

In fact, an X post by Cryer in June 2022 gave fans hope that the pair might one day reunite.

“Just saw Top Gun: Maverick,” posted Cryer. “Think it’s time to reunite with Sheen for Hot Shots: Part Tres.”

The post earned more than 45,000 likes.

There’s much to savor in So That Happened, and the memoir was lauded by book reviewers worldwide. GQ Magazine called the book “completely entertaining,” while The Hollywood Reporter said it was “a wry, self-deprecating, and funny memoir that covers [Cryer’s] 35-year career.”

Extended Family premieres Saturday, December 23rd at 8/7c on NBC, with new weekly episodes returning Tuesday, January 2nd at 8:30/7:30c on NBC. All episodes will be available to stream next day on Peacock.