Jon Cryer Movies
Dark-haired comedic actor Jon Cryer remains best-known for his lovable performance as Duckie Dale in the 1986 teen movie Pretty in Pink. Even though he was 21 years old playing a high school senior, he exhibited a vulnerable yet goofy freshness unlike most other teen stars. The son of Broadway performers, he was schooled in the Bronx before making his film debut in the romantic comedy No Small Affair as a young photographer obsessed with Demi Moore. He made some unfortunate movies after Pretty in Pink, including the Ferris Bueller knock-off Morgan Stewart's Coming Home, which suggested unfair comparisons with actor Matthew Broderick. Other forgettable movies followed until he was cast as the star of the sitcom The Famous Teddy Z, which was then followed by several other short-lived sitcoms. After appearing in the anarchic comedy Hot Shots!, he proved fairly successful with offbeat comedies and independent films. He helped write the talky romantic comedy The Pompatus of Love then starred in the similarly themed Plan B. He teamed up with director Richard Schenkman to write the offbeat comedy Went to Coney Island on a Mission From God...Be Back by Five. After an erratic appearance in the Eddie Murphy movie Holy Man, he went back to television for the sitcoms The Trouble With Normal (with Paget Brewster) and Two and a Half Men (with Charlie Sheen). ~ Andrea LeVasseur, All Movie Guide- Starring:
- Charlie Sheen, Jon Cryer, (more)
A successful author is forced to contend with an unrequited crush from high school upon returning to his hometown to give the commencement speech to the graduating class of seniors. Winona Ryder, Mark Polish, Hilary Duff, Sean Astin, Chevy Chase, and Jon Cryer star in a "knowing-your-age" comedy featuring Lost star Josh Holloway. ~ Jason Buchanan, All Movie Guide
- Starring:
- Mark Polish, Winona Ryder, (more)

- 2007
- Add Unstable Fables: 3 Pigs and a Baby to QueueAdd Unstable Fables: 3 Pigs and a Baby to top of Queue
This decidedly different take on the fable of the Three Little Pigs pokes fun at the fairy tale with a wry sense of humor that both kids and adult will be able to appreciate. In this animated version, the big bad wolf sends a team of Special Ops agents to infiltrate the home of the pigs by leaving an irresistibly innocent baby wolf on their doorstep. The pigs raise him as their own, but when that canine tyke reaches his teens, in identity crisis ensues that might just let the wolves nefariously drawn out plan come to fruition. ~ Cammila Albertson, All Movie Guide
- Starring:
- Jon Cryer, Brad Garrett, (more)
The fourth, Emmy-winning season of the CBS hit Two and Half Men starts with a shock -- Alan Harper (Jon Cryer) is getting divorced, again -- and ends with a rock: That is, the diamond Evelyn Harper's new boyfriend wants to put on her finger, ensuring mixed emotions for Alan and his brother, Charlie (Charlie Sheen). In between, Charlie's hip Malibu beach pad is the place for laughs, gorgeous girls, single parenthood, celebrity neighbors, family, and more laughs. Charlie has a close encounter with his long-deceased dad. Alan, after a few resume embellishments, tries online dating. Jake (Angus T. Jones) swaps his Harry Potter posters for the joys of hottie wall art. Join the fun. Share the good life with everyone's favorite manly men. All 24 episodes of Season 4 (2006-7) are included here, along with commentaries, a featurette, and a gag reel.
- Starring:
- Charlie Sheen, Jon Cryer, (more)
The boys (two-and-a-half-men's worth) are back for a snappy, smart, third season of this CBS comedy hit. The warm heart of the series remains the makeshift family that calls the Malibu beach house home -- carefree bachelor Charlie Harper (Charlie Sheen), his fussy chiropractor brother Alan (Jon Cryer), and Alan's precocious young son Jake (Angus T. Jones). In the 24 episodes of Season 3 (that aired from 2005-06), Charlie romances a beautiful ballet dancer, Alan dates a 22-year-old cutie and his domineering ex-wife...and finally, wedding bells ring, but who's the happy couple?
- Starring:
- Charlie Sheen, Jon Cryer, (more)
Long time bachelor Charlie (Charlie Sheen) and his divorced, uptight brother Alan (Jon Cryer) give a whole new meaning to the word dysfunctional as they attempt to meet women, deal with freak accidents, and share parenting responsibilities for Alan's pre-pubescent indolent son Jake (Angus T. Jones.) Boys will be boys as Alan struggles to guide Jake through life with valuable lessons of morality. Meanwhile, Alan's ex-wife Judith (Marin Hinkle) takes advantage of every opportunity to destroy any self-respect that Alan may have left, and Charlie is forced to deal with the come-ons from his crazy neighbor Rose (Melanie Lynskey). After a year of living together, the guys have figured out how Two and a Half Men equal one family. Sort of. But there are plenty of hilariously rough spots along the way, and you'll share them all in this four-disc collection that includes all 24 episodes of the second season, which aired from 2004-05 on CBS.
- Starring:
- Charlie Sheen, Jon Cryer, (more)
- Starring:
- Christopher Plumley, Lindsay Felton, (more)
Charlie Sheen, Jon Cryer, and Angus T. Jones essayed the title roles in the CBS sitcom Two and a Half Men. The swinging-bachelor lifestyle of commercial-jingle composer -- and chronic gambler -- Charlie Harper (Sheen) was sorely disrupted when his Malibu beach house was invaded by his uptight brother, Alan (Cryer), and Alan's ten-year-old son, Jake (Jones). Given the childish hedonism of Charlie and the domestic immaturity of the soon-to-be-divorced Alan, young Jake turned out to be the true "grown-up" in the Harper household. Also seen from time to time were Marin Hinkle as Alan's ex-wife Judith (who may or may not have been gay); Melanie Lynskey as Charlie's erstwhile lover and next-door neighbor Rose; and Holland Taylor (replacing the pilot episode's Blythe Danner) as Charlie and Alan's control-freak mother, Evelyn. Created by Lee Aronsohn and Chuck Lorre, Two and a Half Men opened to excellent ratings on September 22, 2003. Hal Erickson, All Movie Guide
- Starring:
- Charlie Sheen, Jon Cryer, (more)
- Starring:
- Paget Brewster, David Krumholtz, (more)
This satirical workplace sitcom is set in a Chicago agency, Old Dog Productions, a TV commercials outfit run by Jack Kacmarczyk (Elliott Gould). In the opening set-up, Robyn Buckley (Vivica A. Fox) meets Sam Wagner (Jon Cryer) in a restaurant line. He fixes her up on a blind date with his co-worker Milo Doucette (Duane Martin), but things don't gel well during the date. The next morning, the two guys go to work only to discover that Robyn is their new boss. Later episodes introduced Robyn's mother (Irma P. Hall) and grandmother (Ketty Lester). Premiered April 6, 1998 on Fox. ~ Bhob Stewart, All Movie Guide
- Starring:
- Vivica A. Fox, Duane Martin, (more)
A group of 20-somethings try to sort out their romantic, personal, and professional dilemmas in this sardonic independent comedy. Stuart Winer (Jon Cryer) is an alternately charming and annoying nerd who is struggling to complete his first novel. Gina (Sara Mornell), who works at a successful clothing company, is the model of strength and savvy at work, but at home she's pathetically eager to bend to the will of her latest boyfriend. Jack and Claire (Lance Guest and Lisa Darr) are newly marrieds whose relationship is collapsing under the weight of their unsuccessful attempts to have a baby. And Ricky (Mark Matheisen) is a self-centered actor whose biggest role to date is not doing much for his resume; he played the Ty-D-Bowl man in a TV commercial. Director Gary Leva also appears in a small role. ~ Mark Deming, All Movie Guide
This HBO TV special features Reagan impersonator Jim Morris playing the well-loved President as cartoonist Garry Trudeau sees him. This is based on an off-Broadway show and contains a number of musical sketches and humorous parodies. ~ All Movie Guide
Noon Wine is adapted from a short story by Katharine Ann Porter. Fred Ward stars as a taciturn Swede who is hired to work on a Texas dairy farm. After he puts in nine years of hard and faithful effort, Ward's secret is revealed: when he applied for his job, he was a fugitive from a murder charge. Michael Fields wrote and directed this 90-minute TV drama. Noon Wine was first seen January 21, 1985 on PBS' American Playhouse series. ~ Hal Erickson, All Movie Guide
A Seattle morning show weather girl must struggle to pull her life together after committing career suicide before a live audience in this existential crisis comedy featuring Mark Harmon, Jon Cryer, and Jane Lynch. Sylvia (Tricia O'Kelley) was a notable fixture on Seattle's most popular morning television program before she discovered that her boyfriend, Dale (Harmon), the show's anchor, was cheating on her with his co-host, Sherry (Kaitlin Olson). Her career in television implodes in just the time it takes to have an on-air meltdown, and Sylvia is forced to move in with her slacker brother, Walt (Ryan Devlin), while she tries to get back on her feet. Now Sylvia is 35, unemployed, and single. No one will hire her for fear that she may flip out on a moment's notice, but Walt's best friend, Byron (Patrick J. Adams), sees something in Sylvia that no one else seems to notice. Now, as Walt attempts to show Sylvia that there's more to life than fame and fortune, the woman whose life has just fallen apart wages a valiant effort to finally get over herself and discover the secret to living a more meaningful life. ~ Jason Buchanan, All Movie Guide
- Starring:
- Tricia O'Kelley, Patrick J. Adams, (more)
An FBI agent in the midst of a crucial undercover investigation resorts to extreme measures in order to prove himself in this crime thriller starring Cole Hauser, James Cromwell, and Laurence Fishburne. FBI agent Kevin Cole (Hauser) is under direct orders from powerful crime boss Ziggy to track down millions in stolen cash. As he begins to turn the screws on the shady mob accountant (Fishburne) who may just have all the answers, Agent Cole realizes that the is slowly slipping though his fingers. The mind games have begun, and in a world where ruthlessness is essential to survival, your most recent lie could well be your last. Emmanuelle Chriqui co-stars. ~ Jason Buchanan, All Movie Guide
- Starring:
- Cole Hauser, James Cromwell, (more)

- 1998
- R
- Add Went to Coney Island On a Mission From God...Be Back By Five to QueueAdd Went to Coney Island On a Mission From God...Be Back By Five to top of Queue
Richard Schenkman, who debuted with the disappointing The Pompatus of Love (1996), returned with this comedy-drama, set on the streets of Brooklyn. When young Richie (Rafael Baez) vanishes, rumor has it that he went insane at Coney Island, so pizza guy Stan (Rick Stear) and pawnshop clerk Daniel (Jon Cryer, who co-scripted with Schenkman) spend a winter's day searching for their childhood friend through the deserted amusement park. They encounter a variety of locals in their wanderings, while flashbacks fill in the story of past events, including Stan's alcoholic escapades which ended his relationship with Gabby (Ione Skye). Shown at the 1998 L.A. Independent Film Fest. ~ Bhob Stewart, All Movie Guide
- Starring:
- Jon Cryer, Rick Stear, (more)
This lively and complicated romantic comedy-drama centers on four fellows. Runyon is a poet carrying a torch for Kathryn; he flies to LA to talk about scripting a movie and is accompanied by the lovely Tarzaan. Gadabout Josh is seen having a fling with a Chinese hat-check girl and pursuing Cynthia; despite his womanizing, he also still cares for his ex-wife Gina, the sister of Phil, a plumber and owner of a hardware store who is married with two children. Phil is in a quandary because he finds himself lusting for a sophisticated English coquette who just might be interested in him. Meanwhile, therapist Mark is utterly wrecked over a difficult relationship with Tasha. The title of the film comes from a line in rocker Steve Miller's song, "The Joker". ~ Sandra Brennan, All Movie Guide
- Starring:
- Jon Cryer, Tim Guinee, (more)
Penn & Teller are magicians who are known for putting on a jet-black, fake blood-soaked comedy magic show. This inky comedy is imbued with their off-beat humor as it chronicles Penn's newest scheme to have a fan try to kill him. ~ Sandra Brennan, All Movie Guide
- Starring:
- Penn Jillette, Teller, (more)
Penelope Spheeris, director of the infamous documentary The Decline of Western Civilization may well have given the world its first punk-rock Western in the form of Dudes, a sort of Suburbia meets High Noon meets Deliverance. Three East Coast punks (Jon Cryer, Daniel Roebuck, and Flea of the Red Hot Chili Peppers) opt to leave behind the filth and gloom of New York City to become modern-day pioneers on the trail to California; that is, until a gang of redneck road warrior-types led by Lee Ving (of the punk band Fear) waylay the trio and kill Flea in a fashion brutal enough to justify the inevitable retribution. After their pleas to the local sheriff fall on deaf ears, Cryer and Roebuck decide instead to follow the law of the West and serve their own brand of justice as what appear to be a bondage-oriented cowboy and a squirrel on steroids. While the plot seems contrived and asinine, the violence often gratuitous, and the characters paper-thin, Spheeris nonetheless manages to create a likeable and highly watchable -- if often silly -- film. Cryer and Roebuck do the best they can with the material, Ving plays an adequately loathsome villain, and Flea lends a glimpse of his acting ability by offering a convincing portrayal of a dead body. Nowhere near being the time capsule that is The Decline of Western Civilization, Dudes still offers some insight into the punk subculture of the '80s. Spheeris later directed the hugely successful Wayne's World as well as The Decline of Western Civilization II: The Metal Years. ~ Jeremy Beday, All Movie Guide
- Starring:
- Jon Cryer, Daniel Roebuck, (more)
In what can only be described as a dramatic change of pace, Robert Altman directed this raunchy teen comedy based on the antics of two characters featured in a series of stories published in the National Lampoon. Oliver Cromwell Ogilvie (Daniel Jenkins), aka O.C., and his buddy Mark Stiggs (Neil Barry), are a pair of misfit teenagers whose greatest joy in life is making those around them miserable. O.C.'s ancient grandfather (Ray Walston) has just had his insurance cancelled, and when he discovers that suburbanite salesman Randall Schwabb (Paul Dooley) is responsible, O.C. and Stiggs swing into a summer-long campaign to get revenge on Schwabb and his family. While it received some of the most brutally negative reviews of Altman's career, O.C. and Stiggs is worth a quick look for its cast, which includes fellow outcast auteurs Dennis Hopper and Melvin Van Peebles, comics Louis Nye and Jane Curtain, the one-time glamour girl of the Clifford Irving scandal Nina Van Pallandt, and Thomas Hal Phillips, reprising his role as Hal Phillip Walker from Nashville. World music superstars King Sunny Ade and his African Beats appear and provide the musical score. ~ Mark Deming, All Movie Guide
- Starring:
- Daniel Jenkins, Neil Barry, (more)
This run-of-the-mill teen romantic comedy's main attraction is 22-year-old Demi Moore as Laura Victor, an aspiring rock singer. The slightly younger Jon Cryer is Charles Cummings, a dedicated photographer who meets Laura, falls in love, and decides that a dedication to furthering her career might further his own amorous designs. Charles is essentially a loser when it comes to women -- and just about anything else except photography. One day Charles captures Laura on film along a San Francisco seashore and is shocked but excited to run into her later while at a North Beach nightclub where she is a performer. Unable to just let her go, he finally convinces her to pose for him, and as a result of that session he comes up with one good photo which he then puts on nearly 200 San Francisco cabs -- using up all his savings in the process. The result consists of offers that have nothing to do with singing -- until one exception occurs. Another new face in the crowd in this conventional movie is Jennifer Tilly (younger sister of Meg Tilly and Oscar-nominated for her role in Bullets Over Broadway), working in her first film. ~ Eleanor Mannikka, All Movie Guide
- Starring:
- Jon Cryer, Demi Moore, (more)
From director Jim Abrahams, one of the minds behind the Airplane! and Naked Gun films, comes another parody. This time around, Abrahams has his sights set on the action-adventure genre, specifically Top Gun. Charlie Sheen stars as Topper Harley, a maverick air force pilot who constantly lives in the shadow of his father's legacy. Unable to handle the pressure, Harley has left the Air Force to live among a tribe of Native Americans. But when the United States seeks to destroy some Iraqi nuclear facilities, there's only one man for the job. After being coaxed back into service, Harley soon realizes that in addition to Saddam Hussein, he'll have to contend with a rival pilot, played by Cary Elwes, and a devious aerospace executive. Among the many films lampooned are Dances With Wolves, 9 1/2 Weeks, The Fabulous Baker Boys, and Gone With the Wind. ~ Matthew Tobey, All Movie Guide
- Starring:
- Charlie Sheen, Valeria Golino, (more)


























