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.
In 2003, Cryer re-teamed with Hotshots! co-star Charlie Sheen for the sitcom Two and a Half Men, which proved to be a massive success. The show was so popular that it stayed on the air, even after Sheen left in 2011, with Ashton Kutcher filling in the empty spot in the cast. ~ Andrea LeVasseur, Rovi

- 1984
- R
- Add No Small Affair to Queue
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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, Rovi
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- Starring:
- Jon Cryer, Demi Moore, (more)

- 1984
-
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, Rovi
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- 1985
- R
- Add O.C. and Stiggs to Queue
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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, Rovi
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- Starring:
- Daniel Jenkins, Neill Barry, (more)

- 1986
- PG13
- Add Pretty in Pink to Queue
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John Hughes crafts an exemplary '80s Brat Pack romance out of the standard Cinderella story in Pretty in Pink. Andie Walsh (Molly Ringwald) is a teenager who lives in the dingy part of town with her terminally underemployed dad (Harry Dean Stanton). She works at a record store with eccentric Ionia (Annie Potts) and is considered a misfit at her uppity high school, but somehow she rises above them all. Her oddball best friend, Duckie (Jon Cryer), is hopelessly in love with her, so he causes trouble for her romantic pursuits. When local rich kid Blaine (Andrew McCarthy) develops a fascination with her, they go out on a date together. Visiting the home bases of each social clique, they are basically ridiculed for their audacity to date one another. When Blaine eventually asks the delighted Andie to the prom, he is threatened by his rich friend Steff (James Spader). The romance versus high school social politics finally culminates at the big night of the prom. ~ Andrea LeVasseur, Rovi
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- Starring:
- Molly Ringwald, Harry Dean Stanton, (more)

- 1987
- PG13
- Add Hiding Out to Queue
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Hiding Out, a surprisingly entertaining and engaging action comedy, directed by Bob Giraldi, takes the implausible idea that an adult man could enroll in high school and pass as a student and makes it real. Andrew (Jon Cryer) is a stockbroker hunted by a professional killer. He flees to stay with his sister and her teenage son Patrick (Keith Coogan). Andrew shaves off his beard, cuts his hair, and enrolls in Patrick's high school, pretending to be 17 years old. Cryer does a great job of convincingly playing both ages, and Coogan shines as the teenage son. Director Giraldi has great visual style and gives the film an energy that makes it both enjoyable and believable. ~ Linda Rasmussen, Rovi
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- Starring:
- Jon Cryer, Keith Coogan, (more)

- 1987
- PG13
- Add Morgan Stewart's Coming Home to Queue
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An ambitious father thinks nothing of using his own son to achieve his political goals in this adolescent comedy. The lonely boy has spent the last seven years tucked away and ignored by his parents, Senator Tom Morgan and his social-climbing wife Nancy, in a distant boarding school. As the story begins, he receives the depressing news that once again they will be too busy to have him home for the holidays. But then, out of the blue, they change their minds and invite him home to stay there for good. The boy is elated, but soon after his arrival, he learns the bitter truth: his father only brought him back because it is an election year and his campaign manager thought he might do better if the public saw him as more of a family man. The boy then decides that it is high time some changes were made around the house and mayhem ensues. ~ Sandra Brennan, Rovi
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- Starring:
- Jon Cryer, Lynn Redgrave, (more)

- 1987
- R
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, Rovi
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- Starring:
- Jon Cryer, Daniel Roebuck, (more)

- 1987
- PG
- Add Superman IV: The Quest for Peace to Queue
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Superman (Christopher Reeve) tries to save the world from nuclear destruction at the hands of Lex Luthor (Gene Hackman) in this action film featuring the man of steel. In a speech to the United Nations, Superman declares he will rid the world of all nuclear weapons. Arch-villain Luthor emerges from prison obsessed with killing Superman and creates an adversary known as Nuclear Man (Mark Pillow). The two engage in a fight to the finish in various landmarks on Earth before taking their battle into outer space. When Lois Lane (Margot Kidder) invites both Superman and Clark Kent to a double-date dinner, Superman's powers are tested so that both men can be present. Jackie Cooper plays the gruff veteran newspaper editor Perry White, with Marc McClure as Jimmy Olsen. Sam Wanamaker plays tabloid tycoon David Warfield, the millionaire who buys the Daily Planet. Mariel Hemmingway is Warfield's daughter Lacy, Clark Kent's date at Lois' luxury apartment. This is the least interesting of the four Superman movies starring Christopher Reeve. ~ Dan Pavlides, Rovi
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- Starring:
- Christopher Reeve, Gene Hackman, (more)

- 1988
-
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. ~ Rovi
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- 1990
- R
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
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- Starring:
- Penn Jillette, Teller, (more)

- 1991
- PG13
- Add Hot Shots! to Queue
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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, Rovi
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- Starring:
- Charlie Sheen, Valeria Golino, (more)

- 1994
-
This black comedy stars Jon Cryer as a young reporter following the case of a serial killer who decapitates his victims. ~ Jason Ankeny, Rovi
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- 1995
- R
- Add The Pompatus of Love to Queue
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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, Rovi
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- Starring:
- Jon Cryer, Tim Guinee, (more)

- 1997
- NC17
Josh Evans wrote and directed this cynical glimpse at power players and hustlers working the shadowy side of the film industry. After his mother's death, talented eccentric Sonny Daye (William McNamara) arrives on the Hollywood scene. His brother, Franky Syde (Frank Whaley), confident of Sonny's abilities, allows crass, scurrilous producer Sid Dalgren (Tony Danza) to see Sonny's journal. Recognizing Sonny's gift, Sid makes moves to manipulate and exploit him. Sid's girlfriend, Vanessa (Natasha Gregson Wagner), sees Sonny in a different light. The Glam cast includes director Evans' mother, Ali MacGraw. Some of the Glam character names link with characters introduced in Evans' directorial debut, Inside the Goldmine (1994), a film that also featured Wagner, the daughter of Natalie Wood and Robert Wagner. Shown at the 1997 Vancouver Film Festival. ~ Bhob Stewart, Rovi
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- Starring:
- William McNamara, Frank Whaley, (more)

- 1998
- PG
- Add Holy Man to Queue
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Stephen Herek directed this comedy-drama in which soul-less exec Ricky Hayman (Jeff Goldblum), programmer for the failing Good Buy Shopping Network, is dismayed by a request to increase sales in two weeks. Bald do-gooder guru G. (Eddie Murphy) assists when Ricky and marketing director Kate (Kelly Preston) get a freeway flat. When G. passes out, tests indicate a heart murmur and heat prostration, so the robed prophet becomes Ricky's house guest. At a party, G. uses hypnosis and psychology to rid guest Nino Cerruti (portraying himself) of his flying fears. Ricky witnesses this and gets the notion to put G. on the air. Unfortunately, G. ignores both cue cards and on-sale products, prompting station owner McBainbridge (Robert Loggia) to calculate Ricky's severance pay. He's back on the job when both sales and ratings soar. The situation eventually causes Ricky to reexamine how his own values became lost in the labyrinth of corporate consumerism. ~ Bhob Stewart, Rovi
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- Starring:
- Eddie Murphy, Jeff Goldblum, (more)

- 1998
-
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, Rovi
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- Starring:
- Vivica A. Fox, Duane Martin, (more)

- 1998
- R
- Add Went to Coney Island On a Mission From God...Be Back By Five to Queue
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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, Rovi
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- Starring:
- Jon Cryer, Rick Stear, (more)

- 1998
-
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, Rovi
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- Starring:
- Jon Cryer, Lisa Darr, (more)

- 2000
-

- 2003
-

- 2003
-
- Add Two and a Half Men: Season 01 to Queue
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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
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- Starring:
- Charlie Sheen, Jon Cryer, (more)

- 2004
-
- Add Two and a Half Men: Season 02 to Queue
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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.
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- Starring:
- Charlie Sheen, Jon Cryer, (more)

- 2005
-
- Add Two and a Half Men: Season 03 to Queue
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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?
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- Starring:
- Charlie Sheen, Jon Cryer, (more)

- 2006
-
- Add Two and a Half Men: Season 04 to Queue
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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.
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- Starring:
- Charlie Sheen, Jon Cryer, (more)