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“When did you first feel cancelled by your age?”

You knew that some variation of this question would be asked — it was really just a question of when, and if it would come before the inevitable query about all that nudity. Seven minutes into the Cannes Film Festival press conference for The Substance, writer-director Coralie Fargeat’s extraordinary, extremely gory body-horror movie, a journalist asked the film’s star to talk about getting iced out of Hollywood for being a woman over the age of 40. The fact that the movie...

Ever imagine Alan Harper (Jon Cryer from Two and a Half Men) swapping punchlines for photon torpedoes in a sci-fi series? Cryer actually passed on a role in Sackhoff’s iconic space saga, leaving fans wondering what could’ve been.

Demi Moore and Jon Cryer in No Small Affair | Columbia Pictures

Did he miss his chance at sci-fi glory? Now that’s something we gotta find out!

The Sci-Fi Face-Off: Jon Cryer Reveals the Show He Passed Up for Two and a Half Men! Charlie Sheen and Jon Cryer in Two and a Half Men | Warner Bros. Television

Jon Cryer, the very same actor who gave us the delightfully villainous Lex Luthor in Supergirl, recently revealed a mind-boggling fact on X. He almost traded sitcom laughs for epic sci-fi in Battlestar Galactica.

Back in 2003, when Two and a Half Men was just setting sail on its 12-season journey, Cryer was faced with a tough decision.

The Brat Pack has been through a lot, but time has only strengthened their offscreen friendships.

While discussing Andrew McCarthy’s new Brats documentary at its Tribeca Film Festival premiere on Friday, Jon Cryer had some less-than-fond memories of his Pretty in Pink (1986) co-star.

“When we made Pretty in Pink, we didn’t get along because he was a d***,” said Cryer on a panel Friday with McCarthy, Ally Sheedy, and Demi Moore, according to Entertainment Weekly.

McCarthy admitted to Cryer, “That’s very true,” as Moore disagreed. “Well I didn’t think he was a d***,” she said.

“Well he wasn’t a d*** to you,” Cryer quipped to Moore, whom he dated while working on their 1984 movie, No Small Affair.

Molly Ringwald, Jon Cryer and Andrew McCarthy in ‘Pretty in Pink’

Not talking out of school here, btw, he was sitting two feet away when I said this.

Demi Moore suffered from substance addiction during her younger years, but this was kept secret for a while especially when she got into a relationship with Two and a Half Men actor Jon Cryer. He admitted not having any idea about his ex-girlfriend’s situation.

Demi Moore and Jon Cryer in No Small Affair / Columbia Pictures

After rehabilitation, Moore remained sober for 20 years, but she experienced a relapse in 2012 hence going back into treatment again. She also dealt with eating disorders apart from her addiction.

Jon Cryer Wasn’t Aware Of Ex-Girlfriend Demi Moore’s Addiction Struggles

In the new documentary helmed by Andrew McCarthy entitled Brats, actor Jon Cryer shared via People his short-lived romance with Demi Moore.

We dated for a short time while we were working on No Small Affair, but I guess our particular affair was, in fact, pretty small. She was already struggling with a drug problem.

Actor Jon Cryer, known for starring in the popular sitcom Two and a Half Men, has recently opened up about his association with the 80s ensemble of young stars known as The Brat Pack. The subject of Andrew McCarthy’s latest documentary, The Brat Pack comprised young stars of the era such as Rob Lowe, Andrew McCarthy, and Demi Moore, known for their frequent presence on the big screen.

Jon Cryer in Two and a Half Men

While Cryer was also considered to be part of the group, and even makes an appearance in the upcoming documentary, Brats, the actor has recently shared that he did not perceive himself as cool enough to be classified as a core member.

The Two and a Half Men Star on His Association With The Brat Pack

While starring in the 1984 romantic comedy, No Small Affair, actor Jon Cryer and Demi Moore briefly dated,...

When Hollywood dubbed actors like Andrew McCarthy, Molly Ringwald, Emilio Estevez, Judd Nelson, Demi Moore, and Rob Lowe as members of The Brat Pack, the label triggered an unwanted chain reaction throughout the group. The name came with a specific air, and several Brat Pack members saw the brand as a curse. In Andrew McCarthy’s Brats trailer, the teen comedy icon turned filmmaker explores the ramifications of becoming the poster child for Hollywood’s disaffected youth during the 1980s.

In partnership with Neon and Network Entertainment, ABC News Studios will bring Brats to Hulu in the United States on June 13. A Disney+ premiere will occur in select territories later this summer, following its world premiere at the 2024 Tribeca Festival.

According to the documentary’s official press release:

Brats “looks at the iconic films of the 1980s that shaped a generation and the narrative that took hold when their young...

Duckie may have had it out for Blane, but the feud extended behind the scenes as well, as Jon Cryer and Andrew McCarthy did not jive while making teen movie classic Pretty in Pink. Now, Cryer says that has all settled…but who gets to go home with Andie?

Appearing on The View (per Entertainment Weekly), Jon Cryer said of Andrew McCarthy, “He and I famously did not get along when we were shooting Pretty in Pink…It was because there was tension. Interestingly, I saw him backstage and we had a lovely time, we had a great talk. Thank you!”

Cryer went on to detail why he and McCarthy didn’t get along during Pretty in Pink, citing issues that were far deeper that what we see onscreen. “At any rate, what I realize now, he wrote a terrific memoir called Brat, he was already struggling with alcoholism back...

Two and a Half Men needed another actor to fill the gap in the main cast. The showrunners approached multiple people, and one high-profile star turned down a million-dollar offer. It was not long until Ashton Kutcher received the opportunity to join the cast.

Kutcher agreed to be a lead character and realized he got to star alongside Jon Cryer. Cryer had already worked on various movies and shows beforehand. Kutcher has seen his previous projects and felt excited to work with him.

Ashton Kutcher was in ‘Two and a Half Men’ for four years

In 2011, Kutcher joined the cast of Two and a Half Men during its ninth season. He replaced Charlie Sheen and had the lead role of Walden Schmidt for the show’s last four seasons. The character first appears depressed and tries to drown himself in the ocean.

Afterward, Walden begins to hang around the other central characters.

Jon Cryer has “not a regret in the world” about his brief romance with Demi Moore — but he is correcting the star on the status of his virginity at the time.

The 54-year-old actor denied that Moore, 56, had taken his virginity after she wrote about it in her new memoir Inside Out.

“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 making that assumption based on my my [sic] skill level (and the stunned look on my face at the time), I had actually...

Hollywood is a very small town. In his newly released memoir, So That Happened, Jon Cryer revealed that he once romanced his Two and a Half Men co-star Ashton Kutcher's ex-wife, Demi Moore. Jon, 49, recalled that he and Demi, 52, dated 30 years ago, around the time that they co-starred in the 1984 romantic comedy No Small Affair. When Ashton, 37, replaced Charlie Sheen on CBS' Two and a Half Men in 2011, Jon was afraid to tell him that they shared a mutual ex. "It was awkward in that I'm not sure she even told him that we dated," the actor told Entertainment Tonight Monday. "In our first meeting, we're trying to have that let's-create-that-chemistry meeting, and the whole time I'm...

Jon Cryer's coming clean about his past!  The "Two and a Half Men" star opens up about his dating history in his new memoir, "So That Happened," and spoke candidly up about the tell-all in an interview with Entertainment Tonight.  In the book, Cryer reveals that he and Demi Moore started dating while filming their 1984 romantic comedy, "No Small Affair -- and Demi never told Jon's "Two and a Half Men" costar Ashton Kutcher about their relationship!   "It was awkward in that I'm not sure she even told him that we dated," Cryer confessed in the interview posted on Monday. "In our first meeting, we're trying to have that let's-create-that-chemistry meeting and the whole time I'm looking at him, waiting for him to drop the bomb," he continued.  Demi and Ashton officially finalized their divorce in November 2013 after 8 years of marriage -- during the same time Jon and Kutcher...

Jon Cryer has more in common with his Two and a Half Men costar Ashton Kutcher than fans may realize.

The actor, 49, revealed in his new memoir So That Happened a piece of his dating history involving Kutcher's ex-wife Demi Moore, 52.

Cryer and the actress dated 30 years ago around the time that they starred together in the 1984 romantic comedy No Small Affair, he revealed in the new tell-all, which hit shelves Tuesday.

The most awkward part? They didn't exactly tell his sitcom buddy upfront.

"It was awkward in that I'm not sure she even told him that we dated," Cryer...

It turns out that Jon Cryer shares a bond with his former costar Ashton Kutcher that goes beyond Two and a Half Men. Cryer revealed in his new memoir, So That Happened, that he dated Demi Moore many years before Kutcher began seeing her. More than three decades ago, the Pretty in Pink actor, 49, and fellow brat packer Moore, 52, starred in the 1984 flick No Small Affair. While their relationship fizzled out, Cryer revealed just how small of a world Hollywood is when Kutcher came [...]...

Normally, Nicholas Sparks adaptations are nothing to get excited about, but the cast that is coming together for The Longest Ride, Fox’s latest attempt to find Notebook-style success with a tearjerker from the prolific author, is unusually interesting. We previously reported that Scott Eastwood (yes, son of Clint), Boardwalk Empire actor Jack Huston and acting veteran Alan Alda had boarded the project in leading roles, joining Game of Thrones actress Oona Chaplin and Under the Dome star Britt Robertson, and now we’ve learned that Lolita Davidovich has also signed on.

Davidovich, who recently appeared alongside the late James Gandolfini in HBO original movie Cinema Verite, will play the protective mother of Eastwood’s character, a cowboy who goes out during a blizzard in a race against time to save his family ranch and the love of his life (Robertson). His path intersects with that of an imperiled older...

We’ve really missed seeing living legend Alan Alda (M*A*S*H) at the movies. Outside of playing the antagonist in the forgettable Ben Stiller/Eddie Murphy caper Tower Heist and taking a small supporting role in the also dreary Wanderlust, Alda has been largely absent from the big screen. Luckily, that’s changing now that he has booked the lead role in Nicholas Sparks adaptation The Longest Ride.

In the film, a romantic drama set up over at Fox 2000, Alda will play a man stuck in his car after crashing on an isolated road during a heavy snowstorm. Fighting to stay conscious as he awaits rescuers, the man sees visions of the love of his life, who previously passed away. Meanwhile, outside of the car, there is another romance playing out between a young art history major and a handsome bull rider, who fall in love despite their different personalities,...