Jon Cryer and Charlie Sheen’s on-screen brotherhood turned into a real-life feud, then a cautious reconciliation. Their 12-season run on Two and a Half Men shaped a sitcom legacy and Cryer’s public persona, with 2024 net worth estimates reflecting a career that survived the storm.
Born: April 16, 1965 | Breakout role: Duckie in Pretty in Pink (1986) | Famous TV role: Alan Harper in Two and a Half Men (2003–2015) | Emmy wins: 2 Primetime Emmys | Spouse: Lisa Joyner (m. 2007)
Early Career
- Breakout role in Pretty in Pink (1986)
- 1980s teen heartthrob roles
Two and a Half Men Era
- Played Alan Harper for 12 seasons
- Won 2 Primetime Emmy Awards
- Dealt with Charlie Sheen feud
Post-Sitcom Life
- Starred in Supergirl as Lex Luthor
- Directed and wrote for television
- Net worth of $65 million
Personal Life
- Married to Lisa Joyner since 2007
- One child
- Raised in a show business family
| Attribute | Detail |
|---|---|
| Full name | Jonathan Niven Cryer |
| Date of birth | April 16, 1965 |
| Years active | 1984–present |
| Notable TV roles | Alan Harper (Two and a Half Men), Lex Luthor (Supergirl) |
| Awards | 2 Primetime Emmy Awards, 1 Golden Globe nomination |
| Spouse | Lisa Joyner (m. 2007) |
| Net worth | $65 million (estimated) |
Do Charlie Sheen and Jon Cryer Get Along Now?
After years of public tension, the two actors have made peace—but they remain distant. In a January 2025 interview with E! Online, Cryer said he and Sheen no longer have a relationship, but not in an antagonistic way. “I genuinely wish him well,” Cryer told E!.
“I have not spoken to Charlie. I don’t know that he knows my number anymore.”
— Jon Cryer to Yahoo Entertainment, 2024
Public statements since the show ended
In a May 2026 appearance on Live with Kelly & Mark, Cryer reiterated there is no ill will: “There’s nothing contentious. There’s no ill will between him and me at all.” He also revealed Sheen sent him a message thanking him for participating in a documentary (Yahoo Entertainment).
The timeline of their reconciliation
The turning point came around 2020, when Cryer confirmed Sheen had privately apologized. A 2026 Parade interview revealed Cryer is no longer angry and would be open to meeting Sheen to resolve lingering issues.
What Happened With Jon Cryer and Charlie Sheen?
Becoming the highest-paid actor on CBS
After Sheen’s departure in 2011, Cryer became the highest-paid actor on the network, earning reported $620,000 per episode. The show continued with Ashton Kutcher until 2015.
The feud and the public apology
In 2015, Cryer posted a tribute to Sheen, but Sheen called him a “troll” on social media. Cryer told Yahoo Entertainment that Sheen later apologized privately, and that he was glad Sheen and show creator Chuck Lorre had reconciled.
Did Jon Cryer Get Along With Ashton Kutcher?
Replacing Charlie Sheen
Kutcher joined Two and a Half Men in 2011 amid controversy. Cryer has consistently described the transition as smooth.
Working dynamic on set
In multiple interviews, Cryer praised Kutcher’s professionalism. They remain on good terms, though not close friends.
Is Jon Cryer Nice in Real Life?
Reputation among co-stars
Colleagues describe Cryer as kind and professional. His public persona contrasts sharply with his character Alan Harper.
Public persona vs. Alan Harper
Fans often ask if the neurotic on-screen behavior reflects real life. Cryer’s peers confirm he is warm and grounded.
Does Charlie Sheen Still Get Royalties From Two and a Half Men?
Sheen’s exit and contract terms
Sheen was fired in 2011 but continues to receive residuals from episodes he appeared in. Cryer has acknowledged the financial aspect of their feud.
Residuals from syndication
Because the show remains in heavy syndication, Sheen earns ongoing royalties. Cryer’s net worth of $65 million stems from a different earnings trajectory.
What Is Jon Cryer’s Career Outside of Two and a Half Men?
Early movie roles
Cryer’s breakout was Duckie in Pretty in Pink (1986), followed by several 1980s teen films.
Supergirl and Lex Luthor
From 2019 to 2021, Cryer portrayed Lex Luthor on The CW’s Supergirl, bringing dramatic depth to the iconic villain.
Net worth and family
Estimated at $65 million, Cryer’s wealth comes from acting, directing, and writing. He is married to TV host Lisa Joyner and has one child.
The implication: Cryer has successfully diversified his portfolio, moving from sitcom king to dramatic villain, while maintaining a reputation for grace.
Timeline
- 1986: Cryer stars in Pretty in Pink as Duckie.
- 2003: Two and a Half Men premieres on CBS.
- 2011: Charlie Sheen fired; replaced by Ashton Kutcher.
- 2015: Cryer posts tribute; Sheen calls him a ‘troll’; show ends.
- 2020: Cryer states Sheen apologized and they reconciled.
- 2023: Cryer continues acting and guest-stars in various shows.
Related reading: Aaron Paul: Biography, Net Worth, Age, and Why He Stopped Acting
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For a detailed look at Jon Cryer’s career and feud with Charlie Sheen, check out Jon Cryers career and feud.
Frequently Asked Questions
Did Jon Cryer win any awards for Two and a Half Men?
Yes, he won two Primetime Emmy Awards for Outstanding Supporting Actor in a Comedy Series (2012, 2013).
How tall is Jon Cryer?
He is approximately 5 feet 10 inches (178 cm).
Who did Jon Cryer play in Pretty in Pink?
He played Duckie, the quirky best friend.
Is Jon Cryer related to any other actors?
His father, David Cryer, is a Broadway actor and singer; his family includes other entertainers.
What is Jon Cryer doing now?
He continues to act, guest-starring on shows like Supergirl and The Goldbergs, and has directed episodes.
Did Jon Cryer write any of the Two and a Half Men episodes?
He co-wrote one episode in season 8, “Anchorman’s Apprentice.”
Was Jon Cryer in a relationship with Demi Moore? (Unconfirmed)
Rumors persist, but Cryer has never confirmed any romantic involvement with Moore.
Arthur Oliver Howard Fletcher is a staff writer for NationalReport.uk, covering UK national news, politics, the economy and public services. He works under Editor-in-Chief Andreas Christodoulou and UK Managing Editor Rebecca Morgan, following the newsroom standards for sourcing, verification and fact-checking set out in our editorial policies.