Jon Cryer's career has had a lot of twists and turns over the decades.
But you may be shocked to learn that at one point,
he was asked to star in Quentin Tarantino's violent classic "Reservoir Dogs."
Jon Cryer's long career in the entertainment industry began in the 1980s when he was still
a teenager. After debuting in the romantic comedy "No Small Affair" alongside Demi Moore in 1984, he
catapulted to fame in the 1986 John Hughes classic "Pretty in Pink" as the iconic 80's nerd Duckie.
Yet in the decades following his movie debut, Cryer gradually appeared in fewer and fewer films,
with "Superman IV: The Quest for Peace" and "Hot Shots!" being some of the few
big projects he was involved in. By the 90s he had transitioned mostly to television roles,
but while he remained in demand as a guest star,
his attempts to headline a series all flopped, with all of his shows quickly canceled.
Almost two decades after his film debut, Cryer suddenly had a career resurgence
when he landed the role of Alan in the hit sitcom "Two and a Half Men." Starting in 2003,
the long-running comedy series was on air for an impressive 12
seasons before it ended in 2015. The part earned him two Emmys,
one for Outstanding Supporting Actor in a Comedy Series in 2009 and another as Lead Actor in 2012.
But even years before the show's finale, there were major controversies that dragged
the production down. One of the most notorious controversies was the chaotic departure of Cryer's
co-star, Charlie Sheen, in 2011. Executives at Warner Bros. Television fired the actor,
who was currently awash in scandal, for too many missed rehearsals, forgetting lines,
and for simply making the set a toxic work environment. The negative press
surrounding the series then continued with the damaging remarks of actor Angus Jones,
who called it "filth" and begged viewers to stop watching.
The show lived on for a while after the exit of Sheen, with Ashton Kutcher brought on
board to boost ratings. But after four seasons anchored by Cryer and Kutcher,
the network finally pulled the plug in 2015.
Following the conclusion to the "Two and a Half Men" series, Jon Cryer secured an
iconic role as the infamous villain Lex Luthor in "Supergirl" in 2018.
Cryer was featured in 20 episodes during the last few seasons of the superheroine's show,
and he also made an appearance as the legendary supervillain in several others of the DC
Arrowverse, including, "Arrow," "Batwoman," "The Flash," and "DC's Legends of Tomorrow."
When "Supergirl" ended in 2021, though, so did Cryer's time as Lex Luthor. Even
though fans hoped he might continue the role in the series "Superman & Lois,"
Luthor was ultimately recast. The former Walking Dead star Michael Cudlitz took on
the role instead. Cryer cleared the air about the recasting by posting on Twitter, sharing:
"For the record, the folks at DC were very cool and gave me a heads up that the show was going
a different way with [the] character before they started looking. Most of the time, actors
learn about this stuff when it comes out in the trades. I'm grateful they were classy about it."
In 2011, while still starring on "Two and a Half Men," Cryer accepted the lead role in the animated
Pixar film "Planes." At the time, the actor seemed ecstatic about the news, as he told ET,
"To be a part of a Disney movie is a blast because every person has that connection
with Disney movies that they had as a kid. [...] Being a part of a Disney movie is something I have
always wanted to do. [...] When this opportunity presented itself, I just jumped on board."
But just a few months before the scheduled release of the movie in summer 2013,
the studio announced that Dane Cook had replaced Cryer. No explanation for the switch was given,
though director Klay Hall emphasized in a press release that the addition of Cook would
give the main character, Dusty, both a quick wit and an edge. Ultimately, though the film
was a critical failure, it did well enough to earn a sequel – which also starred Cook.
Probably the most substantial reason that Jon Cryer has not appeared much in entertainment
news recently is simply because his new comedy show on NBC has not come out yet.
In 2022, it was announced that Cryer would be executive producing and headlining a new comedy
that is set to co-star Donald Faison and Abigail Spencer. So far, though,
the show hasn't begun filming yet, or even been given a name, much less a firm release date.
The family comedy will be about the complicated nature of life with kids after a divorce and the
drama that can arise even as the former couple gets along. It's far too early
to speculate about how the show will perform or whether it will have legs on the network,
but if it's a hit, Cryer will be back in the spotlight for another sitcom success.
Early in his career there were several major roles early on that Cryer auditioned for but didn't get,
any one of which could have significantly altered the trajectory of his career.
Cryer auditioned for the lead role in the 1985 classic "Back to the Future" but was
ultimately rejected in favor of Michael J. Fox. He was also asked to audition for the
role of Mr. Pink in Quentin Tarantino's 1992 classic "Reservoir Dogs," but Cryer
declined because he did not fully understand the script. Steve Buscemi got the job instead.
Cryer later realized his mistake, telling Howard Stern he still regretted the decision.
"I just had to beg off and not audition for what ended up being a brilliant movie."
He also auditioned for the part of Chandler in "Friends," but he
told James Corden that his audition tape didn't make it to the producers in time.
"She packaged up the tape of me doing my best Chandler Bing,
sent it to Los Angeles, and it got stuck at customs."
He's since said that he loves Matthew Perry's performance on the show. Cryer told Howard
Stern he would have been "decent" as Chandler, but not up to Perry's level,
which took the sting out of losing the role. He said,
"When I see an actor hit it out of the park, it's like, 'Well,
of course, no wonder they gave it to that guy.'"
During the Writers Guild of America strike in 2007 when all of Hollywood was effectively shut down,
"Two and a Half Men" was one of the numerous productions put on hold. But Jon Cryer did
not simply take a break from work during this period. Instead, he showed solidarity with his
fellow creatives by participating in the massive labor action. Cryer told A Socialite's Life,
"It's sad that this has been really hard for a lot of people. Most of the crew on
our show are really gonna miss the money, and with Christmas coming up,
this is just hellish. But I really feel like their anger, which is absolutely justified,
should be directed at the studios. They've been intransigent and ridiculous in the negotiations."
Just as Jon Cryer's time as Alan Harper was coming to a close with the end of
"Two and a Half Men," the actor completed his memoir, "So That Happened." Released in 2015,
the book tells the story of working in Hollywood from his perspective,
along with the important relationships he has formed with other stars in the industry,
such as Charlie Sheen, Demi Moore, Molly Ringwald, and many more.
As Cryer explained on "Good Morning America," it was his manager and agent that approached
him with the idea to tell his tale, which the actor reluctantly agreed to
only after the duo secured a book deal for him. Of particular note in the book is his
discussion of Sheen's infamous meltdown and firing from "Two and a Half Men."
"Charlie made the choice that that was not the life he wanted any more."
Cryer said that he'd reached out to Sheen about writing the book
and that his old co-star was supportive of him.
Outside of his career in the entertainment industry, Jon Cryer has a deep fascination
with true crime podcasts. He also follows controversial court cases,
especially the investigation and trial of Adnan Syed that was thoroughly covered in
the popular "Serial" podcast. By 2016, Cryer had already taken this hobby to Twitter,
where he discussed theories with other podcast hosts and those deeply interested in the subject.
Eventually, Cryer's social media interactions led to his being asked by Susan Simpson of
"Undisclosed" to host segments for the second season of the podcast,
which he enthusiastically accepted. In an interview with Rolling Stone, Cryer said,
"I'm not a lawyer, I just have an avid interest in this stuff, and the 'Undisclosed' team was hoping
that I would host a fan interaction show like 'The Talking Dead' is for 'The Walking Dead.'"
Leading up to the 2016 presidential election, Jon Cryer became vocal about his opposition to Donald
Trump. In an episode of "The Real," Cryer compared his former co-star Sheen to Trump, saying,
"I worked with a guy who also, whenever he said whatever came to the top of his head,
people loved it. And people loved it even more when he said horrible things."
Cryer explained that, having lived through it once,
those traits weren't what he wanted from a political leader.
"I don't want people to pick the president based on entertainment value."
After four years of Trump's presidency, the actor's outspokenness only increased and led
to a Twitter feud with Representative Matt Gaetz in 2020 for his staunch support of the
GOP leader. A month later, Cryer was so disgusted with the actions of the president that he Tweeted,
"I'm a registered independent voter. I've voted for and supported both Republicans
and Democrats in the past. But the GOP's conversion to the cult of Trump has made
it clear [...] I will never vote for another Republican ever again. Period."
For a few years leading up to its premiere in May 2022, Jon Cryer collaborated with his mother,
Gretchen, to create a new play series called "True Stories." The stage production
was a collection of individual stories by solo performers about problems with men,
parent issues, and coming of age, with Cryer's one-man show being called "The Actor's Nightmare."
Cryer ultimately pulled various pieces from his memoir to craft a show about
his life experiences. He told Spectrum News NY1,
"It's mostly about my relationship to starting in the theater, and it's ironically a love
letter to the theater, even though it's got 'nightmare' in the title. Because once COVID
hit and we were sort of robbed of any life in the theater, you realized what was missing.
So I had written a book years ago that had a lot of stories about my life in the theater,
and we realized there was actually sort of a cohesive narrative to it."
Unfortunately, Cryer unexpectedly had to cancel
all performances. That sounds like a true actor's nightmare, doesn’t it?
Jon Cryer may not have made any on-screen appearances in 2022,
but that also didn’t mean he was absent from all TV productions. Instead,
the actor was featured as the narrator for the Vice docuseries,
"Devoured," which tells the story of true crimes associated with food. Cryer told Deadline,
"Just when I thought there couldn't be a genuinely new twist on true crime,
I got 'Devoured.' [...] While I can only aspire to the greatness of, say,
Bill Kurtis or Keith Morrison, it's an honor to lend my voice to this."
Morgan Hertzan, an executive at Vice, seemed just as pleased to have the actor involved, saying,
"Having as immense a talent as Jon Cryer narrate ['Devoured'] is really exciting for us."
On top of Jon Cryer's side projects over the last few years, the actor has also dedicated his time
and resources to the altruistic goal of helping fight homelessness. Sixty-nine thousand people
face homelessness in Los Angeles County, and L.A. Mayor Karen Bass declared the ongoing,
decades-long crisis a state of emergency in January 2023.
Cryer's response has been to help supply tiny homes for individuals
who are struggling with homelessness in the Los Angeles area. Tiny houses are a trend to
help house homeless people, providing them with amenities such as showers,
laundry units, and electrical outlets. Cryer told ET,
"This is a way to give them a real home. A real place with privacy and a place where they can
feel like a human being again for an amount of money that isn't going to crush people."