30 Best Movies About Cheating & Infidelity (2024)

Being cheated on is generally a brutal and heartbreaking occurrence, and sometimes the person doing the cheating ends up getting hurt too — this is especially explored in cheating wife movies or cheating husband movies. However, infidelity has provided Hollywood with some very compelling and dramatic cheating movies. Whether it’s jilted lovers or murdered souls out for revenge, adultery has been a catalyst for some truly romantic or tragic stories that explore this subject from every angle. Movies about cheating and infidelity aren’t always about sex, though.

Using the tantalizing subject matter, these movies can tell each side of the relationship’s story, what led to the affair, whether it was justified, and the ramifications. Many of these cheating movies provide audiences with either a fantasy or a cautionary tale while telling them something about their own lives. They can show the damage that can be done as a result as well as the human moments that emerge from an affair. While cheating movies tend to be rarer than epic romantic films, the trope still exists.

30 Closer (2004)

An Affair Ripples Between The Lives Of Four People

Closer (2004)

Closer is a drama film directed by Mike Nichols, featuring Jude Law, Natalie Portman, Julia Roberts, and Clive Owen. The film explores the intricate and tumultuous relationships between two couples in London, focusing on themes of love, betrayal, and the complexities of human connection. The intersecting romantic entanglements among the four main characters serve as a deep dive into the nature of intimacy and honesty.

Director

Mike Nichols

Release Date

December 3, 2004

Runtime

104 Minutes

Based on a play by Patrick Marber, Closer is an intense drama with a star-studded cast and overseen by an iconic director. Mike Nicholas (The Graduate) directs this tale of two couples who become intertwined by an affair. Jude Law and Julia Roberts play two strangers who meet and form a fast connection with each other, leading to them having an affair. When their respective partners find out (played by Natalie Portman and Clive Owen), it consumes the four individuals with pain and distrust.

The movie is an intimate and engrossing look at these central relationships, with the four actors being the only real major roles in the project. Closer examines the pain infidelity can cause a person and how it can manifest itself in depression, bitterness, vindictiveness, and paranoia. The four actors are excellent in delivering this brutally honest tale with Portman and Owen both receiving Oscar nominations for their performances.

29 The Man Who Wasn’t There (2001)

A Man Blackmails His Wife’s Lover

The Man Who Wasn’t There

The Man Who Wasn’t There is directed by Joel and Ethan Coen and stars Billy Bob Thornton as Ed Crane, a small-town barber in 1949 California. The film follows Crane’s involvement in a blackmail scheme that spirals out of control, drawing him into a complex web of deceit and moral ambiguity. The film’s monochromatic cinematography and meticulous storytelling pay homage to classic film noir.

Director

Joel Coen

Release Date

November 16, 2001

Runtime

116 minutes

The Coen Brothers have been known for their love of noir movies and recreating them with their own unique touches. Such is the case with the period story The Man Who Wasn’t There, which is infused with the dark and oddball humor that only the Coens can pull off so well. Billy Bob Thorton plays Ed Crane, a barber in the 1940s who keeps to himself and is withdrawn from the world. Looking for cash for an investment opportunity, Ed decides to blackmail a local businessman (James Gandolfini) who is having an affair with Ed’s wife (Frances McDormand).

It is the kind of story that would often be seen in noir stories, but Ed gives a new kind of character at the center of it. He is a man who seems largely unbothered by things and doesn’t even seem to take exception to the affair, only seeing it as an opportunity to profit from. However, there is an underlying sweetness to the movie as Ed finds himself getting deeper and deeper into trouble, coming to the realization that he might not have been the kind of husband his wife deserved.

28 Sex, Lies, And Videotape (1989)

Two People Connect Amid Sexual Frustrations

Sex, Lies, and Videotape (1989)

Sex, Lies, and Videotape is a drama film that explores the complex web of relationships between four people, including a troubled marriage, an illicit affair, and a voyeuristic outsider, all of whom are connected by their obsessions and desires.

Release Date

August 4, 1989

Cast

Andie MacDowell , Peter Gallagher , James Spader , Laura San Giacomo , Ron Vawter

Runtime

101 Minutes

Sex, Lies, and Videotape is seen as one of the most influential movies of the American independent cinema movement of the late 1980s and early 1990s. Steven Soderbergh wrote and directed this movie that stars James Spader as a man struggling with his own sexual issues who videotapes interviews with women discussing their own sex lives. When he reunites with an old friend (Peter Gallagher), he begins interviewing the friend’s wife (Andie MacDowell), who is unaware her husband is having an affair with her sister (Laura San Giacomo).

The movie is a thrilling, engrossing, and complex exploration of human sexuality and the many neurotic attributes that go along with the passionate elements. Sex, Lies, and Videotapes shares elements with the Chinese masterpiece In the Mood for Love, as it examines the way two people on the outside of an affair form a connection that is deeper than any they have experienced.

27 Walk The Line (2005)

Johnny Cash And June Carter’s Legendary Affair

Walk The Line (2005)

Walk the Line is a biographical drama film that tells the story of Johnny Cash, a legendary musician, and his tumultuous relationship with June Carter, a country singer. The film stars Joaquin Phoenix as Cash and Reese Witherspoon as Carter, and explores their romance, as well as Cash’s struggles with addiction and fame.

Release Date

September 13, 2005

Runtime

136 Minutes

Walk the Line is the true story of Johnny Cash’s musical career as well as his romance with fellow country legend June Carter Cash. While the movie is most remembered as a solid musical biopic, it is also an examination of the more difficult aspects of this love affair. Johnny was a rising star in the music business when he first met June. He was also married but became infatuated with the singer. After developing a popular on-stage dynamic, the two began an affair as their respective careers went in different directions.

Joaquin Phoenix and Reese Witherspoon are exceptional in their roles as the two music legends and the complexities of their relationship make the story all the more interesting. Both characters are filled with guilt and shame about the way their romance began and it puts a barrier between them from truly embracing their love. However, it also looks at how this developed into one of the most heart-warming music romances of all time.

26 An Education (2009)

A Young Girl Falls For An Older Conman

Carey Mulligan earned her first Oscar nomination for her breakout role in the coming-of-age drama An Education. Mulligan stars as Jenny, a teenage schoolgirl with a bright future who finds herself being seduced into an exciting romance with an older man named David (Peter Sarsgaard). While Jenny is caught up in the romance, it becomes clear that David is not who he says he is and she eventually learns that he is married.

The movie is a compelling and heartbreaking story of Jenny being exposed to the lies and deceit of an adult romance at such a young age. There is a devastating scene in which Jenny goes to David’s house to confront him about the truth only to meet his wife and learn that this is not the first time this has happened. It makes it all the more harrowing as Jenny was balancing the idea of giving up her bright future to be married to a man who she didn’t truly know.

25 Love, Actually (2003)

A Heartbreaking Case Of Cheating In A Romantic Film

Love Actually

The 2003 romantic comedy Love Actually follows various couples as they explore their relationships throughout the Christmas season. With a star-studded cast composed of Bill Nighy, Colin Firth, Alan Rickman, Emma Thompson, Keira Knightley, Hugh Grant, Laura Linney, Liam Neeson, Rowan Atkinson, Chiwetel Ejiofor, Martin Freeman, and Martine McCutcheon, Love Actually has since become a Christmas staple for rom-com lovers.

Release Date

November 14, 2003

Director

Richard Curtis

Runtime

135 minutes

While it is also a great Christmas movie enjoyed by many during the holiday season, Love, Actually offers an intimate look at a variety of different relationships. While most of them are sweet stories of new romances blooming or people expressing their love for each other, there is one heartbreaking cheating subplot. The movie takes a look at various intersecting stories of love and romance around the holidays with an all-star cast.

One of those stories features Emma Thompson as a wife and mother married to Alan Rickman, who finds out he is having an affair with his employee on Christmas Eve. While there is also a cheating element to another story with Colin Firth’s character finding out that his girlfriend is sleeping with his brother, the storyline between Thompson and Rickman is more central. Despite the humor and big romantic moments, the most memorable scene in the movie is Thompson sneaking away from her family’s celebrations to cry alone in her bedroom.

24 American Beauty (1999)

Infidelity Breaks Down A Family

American Beauty (1999)

American Beauty, released in 1999, is a drama film directed by Sam Mendes. It follows the life of Lester Burnham, played by Kevin Spacey, a disillusioned suburban father undergoing a profound midlife crisis. Annette Bening co-stars as his ambitious wife, Carolyn. The film explores themes of beauty, desire, and existential ennui within the confines of American suburbia.

Director

Sam Mendes

Release Date

September 15, 1999

Runtime

122 minutes

Sam Mendes’ Best Picture-winning American Beauty takes a bleak and cynical look at suburban life and the need to escape its monotony. Kevin Spacey won an Oscar for his role as a bored family man going through a midlife crisis while his wife has an affair with her colleague. The movie treats the affair as one more example of this family’s broken nature that none of them are willing to fix.

The movie is an intense drama at times, but there are also moments of dark comedy, such as when Spacey’s wife and her lover go through a fast food drive-thru in the midst of their affair, only to find Spacey working his new job and taking their order. His smiling and happy demeanor while taking their order is matched by their hilarious shocked and confused reaction to being caught in such an unexpected way.

23 Crazy, Stupid, Love (2011)

Infidelity Prompts A New Lease On Life

Crazy, Stupid, Love(2011)

Written by Dan Fogelman and directed by both Glenn Ficarra and John Requa, Crazy, Stupid, Love is a Comedy and Romance film starring Emma Stone, Julianne Moore, Steve Carell, and Ryan Gosling. The plot sees a variety of characters and explores how all of their lives are interconnected by love.

Release Date

July 29, 2011

Director

Glenn Ficarra , John Requa

Runtime

118minutes

One of the funnier and more lighthearted cheating wife movies, Crazy, Stupid, Love is a hilarious and charming star-studded movie. Steve Carell stars as a man going through the motions in life only to learn that his wife (Julianne Moore) is having an affair. The moment shakes him out of his funk as a younger man (Ryan Gosling) takes him under his wing to teach him how to pick up women.

The movie gives a refreshing approach to this story, as Moore’s character is not seen as a villain but rather someone who was at a loss in her marriage and made a mistake. While Carell’s main character finds his more charismatic side as a single man, he also realizes that he took his wife for granted.Crazy, Stupid, Love features a likable ensemble with a secondary romance story between Gosling and Emma Stone adding to the story and also setting up a hilarious twist.

22 The Descendants (2011)

George Clooney’s Character Learns To Grieve For His Cheating Wife

The Descendants

Based off of the 2007 novel, The Descendants is a comedy-drama that follows Hawaii attorney Matthew King and his family as they are forced to reckon with the family land inheritance from Matt’s father. Pressured to sell the land and split it up amongst his financially irresponsible extended family, Matt struggles to deal with the burden after his wife falls into a coma, leaving him to care for his two children in her absence.

Release Date

December 9, 2011

Director

Alexander Payne

Cast

Amara Miller , Shailene Woodley , Robert Forster , George Clooney , Beau Bridges , matthew lillard , Judy Greer , Nick Krause

Runtime

115 minutes

The moment a character learns their wife has been cheating on them is often a powerful scene, but The Descendants sets up a very complicated set of circ*mstances with a lot of emotions at play. George Clooney received an Oscar nomination for his role in this complex comedy-drama as he plays a man whose wife falls into a coma after an accident and with no chance of her waking up. As he makes arrangements for her passing on, he finds out that she was cheating on him with another married man.

The concept of dealing with losing a partner while also dealing with their betrayal is a fascinating one, as Clooney’s performance sells the conflict in this man who is filled with anger and sadness simultaneously. The Descendants earned several Oscar nominations while also winning Best Screenplay.

21 Blood Simple (1984)

A Cheating Wife And Her Beau Are Targeted By A Hitman

Blood Simple

Blood Simple is a neo-noir crime film directed by Joel and Ethan Coen in their directorial debut. Released in 1984, the story follows a Texas bar owner who hires a private detective to kill his wife and her lover. The film features a complex narrative of mistrust, betrayal, and violence, starring Dan Hedaya, Frances McDormand, John Getz, and M. Emmet Walsh.

Director

Joel Coen

Release Date

October 12, 1984

Runtime

96 Minutes

With their debut movie, the Coen Brothers delivered an expert noir movie as well as one of the most intense cheating movies of all time. Blood Simple follows a man who begins an affair with his cruel boss’s wife. When the boss becomes overcome with rage when the evidence of the affair is presented to him, he hires a seedy private detective to kill them.

What follows is a brilliant and exciting tale of suspicion and broken trust that showcases the Coens’ brilliant style. It is a small movie but feels thrilling with the intense sequences and rich characters who fill out the story. It marks Frances McDormand’s breakout role as the cheating wife who becomes the hero of the story. It also features one of the most underrated movie villains of all time in M. Emmett Walsh’s disturbingly gleeful detective.

20 Indecent Proposal (1993)

One Transaction Dooms A Marriage

Indecent Proposal

Indecent Proposal is a drama film directed by Adrian Lyne. Released in 1993, the movie stars Demi Moore and Woody Harrelson as a couple facing financial struggles. Their lives are thrown into turmoil when a billionaire, portrayed by Robert Redford, offers them a million dollars in exchange for one night with the wife. The film explores the moral and emotional ramifications of this provocative proposition.

Director

Adrian Lyne

Release Date

April 7, 1993

Cast

Robert Redford , Demi Moore , Woody Harrelson , Oliver Platt , Seymour Cassel

Runtime

118 Minutes

In Indecent Proposal, Demi Moore and Woody Harrelson star as a loving couple, David and Diana, who have fallen on hard times, and a moment of desperation tests their love for each other. The titular proposal comes when a wealthy man, John, offers the couple $1 million in exchange for one night with Diana. After much thought, the couple agrees because they really need money. However, as the months go by, knowing that his wife and John have been together is too much for David, ultimately pushing her into John’s arms.

In the Adrian Lyne movie, the questionable topic of John “buying” Diana for an evening (and only asking David’s permission, not hers) has always been criticized, and the movie received poor reviews upon release. However, Indecent Proposal went on to be a massive hit and, to this day, is a cautionary tale about desperation and the consequences of one’s actions.

19 The Girl On The Train (2016)

Obsession And Infidelity Become A Murder Mystery

The Girl on the Train

The Girl on the Train is a psychological thriller about a recovering alcoholic who witnesses a shocking crime. With the police unwilling to act, she decides to take matters into her own hands but soon begins to question the events unfolding around her. Emily Blunt plays the lead, withRebecca Ferguson, Haley Bennett, and Justin Theroux just a few of the other big names supporting.

Release Date

October 7, 2016

Director

Tate Taylor

Cast

Allison Janney , Justin Theroux , Emily Blunt , Rebecca Ferguson , Edgar Ramirez , Laura Prepon , Luke Evans , Haley Bennett , Lisa Kudrow

Runtime

120minutes

Based on Paula Hawkins’ debut novel, The Girl on the Train featured Emily Blunt in a standout performance as Rachel, an alcoholic obsessed with her ex-husband. She takes the train every single day, not always entering or exiting it sober. One of her favorite sights on her commute is Scott and Megan, a seemingly idyllic couple. After she (believes she) sees Scott murder Megan, Rachel gets wrapped up in a missing person case that may have larger implications regarding her potential innocence or guilt.

Hawkins’ book was a fun summer read, but the film adaptation was clearly trying to emulate the visual palette seen in David Fincher’s Gone Girl. That movie is widely seen as the superior of the two, but The Girl on the Train still has an incredible cast anchored by an intense Emily Blunt lead performance which earned her nominations for SAG and BAFTA awards.

18 What Lies Beneath (2000)

A Cheating Husband Suffers Supernatural Consequences

What Lies Beneath

What Lies Beneath is a supernatural thriller directed by Robert Zemeckis, featuring Harrison Ford as Dr. Norman Spencer and Michelle Pfeiffer as his wife, Claire. The story revolves around the couple as they experience terrifying events in their seemingly perfect lakeside home, leading Claire to question her sanity and the dark secrets of their past. The film delves into themes of supernatural horror and psychological suspense.

Director

Robert Zemeckis

Release Date

July 21, 2000

Cast

Harrison Ford , Michelle Pfeiffer , Diana Scarwid , Joe Morton , James Remar , Miranda Otto

Runtime

130 Minutes

While infidelity is often used in movies for heavy dramatic storylines of characters dealing with these implications, betrayal can also set the stage for an intense thriller. In What Lies Beneath, Harrison Ford plays Norman, a man whose affair comes back to haunt him in a very literal sense. After noticing some strange occurrences in their house, Norman’s wife, Claire, discovers he had an affair with a woman who died and now is quite possibly haunting their house, which leads to more dark secrets coming to the surface.

Written by Clark Gregg, acclaimed director Robert Zemeckis channels his inner Alfred Hitchco*ck, delivering a suspenseful, slow burn that culminates in an explosively gripping finale. Even Alan Silvestri’s score is reminiscent of Hitchco*ck’s frequent composer, Bernard Herrmann. With Ford teaming with fellow acting legend Michelle Pfeiffer, the movie became a huge hit.

17 Unfaithful (2002)

Tastefully Erotic Cheating Wife Movie Starring Richard Gere

Unfaithful

Unfaithful is a psychological thriller directed by Adrian Lyne. The film stars Richard Gere and Diane Lane as a married couple whose relationship unravels after the wife engages in an extramarital affair with a younger man, played by Olivier Martinez. As the affair intensifies, it leads to unforeseen consequences that put their marriage and lives in jeopardy.

Director

Adrian Lyne

Release Date

May 10, 2002

Runtime

124 Minutes

Director Adrian Lyne tackles infidelity once again with the aptly titled, Unfaithful. Richard Gere and Diane Lane star as Edward and Connie, a couple in a passionless marriage. However, Connie’s chance encounter with a younger man, Paul (Olivier Martinez), leads to a passionate affair. Ultimately, Edward’s discovery of the affair leads to a downward spiral of events which leads to deadly consequences.

Lyne, famous for his tastefully erotic films, crafts a thriller for adults that might spark debate and discussion between the married couples who decide to watch it. It is another movie in which the cheating wife is made to be a complex character, who despite her extramarital betrayal, is the hero of the story. Lane steals the show with her complex and layered performance, which earned her Golden Globe and Academy Award nominations.

16 Fatal Attraction (1987)

A Cheating Husband Encounters One Of Cinema’s Most Iconic Villains

Fatal Attraction

Dan Gallagher, a successful lawyer with a seemingly perfect family life, faces unimaginable turmoil after a brief affair with Alex Forrest. Initially, their fling appears to be a momentary lapse in judgment, but Alex’s intense and unstable behavior soon reveals her deep obsession. As Alex’s fixation on Dan grows, she begins to infiltrate his life, threatening his marriage, career, and even his family’s safety.

Director

Adrian Lyne

Release Date

September 18, 1987

Cast

Michael Douglas , Glenn Close , Anne Archer , Ellen Hamilton Latzen , Stuart Pankin , Ellen Foley

Runtime

119 Minutes

A rare example of an erotic thriller nominated for the Best Picture Oscar is Fatal Attraction. One of the more critically acclaimed cheating movies is directed by Adrian Lyne and stars Michael Douglas as Dan who, despite having a happy marriage, ends up involved in a passionate affair with Alex. However, after Dan puts an end to the affair, Alex won’t give him up, won’t be ignored, and begins exhibiting obsessive and dangerous behavior toward him.

The movie was a huge hit that served as an exciting and intense thriller. Impeccably cast and tension-filled throughout, Fatal Attraction remains a sexually charged but tragic thriller that delivers Glenn Close’s Oscar-nominated role as one of the most iconic movie villains. Showing the movie’s impact years later, there are still debates on how fair it was to depict Alex as the villain of the story.

15 Brothers (2009)

Perceived Infidelity Opens Old War Wounds

Brothers (2009)

Brothers is a 2009 drama film directed by Jim Sheridan. It stars Tobey Maguire as Sam Cahill, a soldier presumed dead, and Jake Gyllenhaal as his brother Tommy. Natalie Portman plays Grace, Sam’s wife, who finds comfort in Tommy during Sam’s absence. Upon Sam’s unexpected return, the family dynamics take a turn as they navigate the complexities of his traumatic experiences and the altered relationships within the family.

Director

Jim Sheridan

Release Date

December 4, 2009

Runtime

105 Minutes

This underrated war drama focused on what happens when a POW comes home and the strained relationships that come as a result. Tobey Maguire plays Sam Cahill, a veteran who was held in a Taliban village and declared K.I.A. by the US military. Sam’s brother, Tommy (Jake Gyllenhaal), begins entwining himself in the lives of Sam’s family, including his wife, Grace, and daughters Isabelle and Maggie.

There actually is no affair in Brothers (just a swiftly regretted kiss), but Sam thinks there was. He’s forced to kill a fellow soldier while being held captive and returns to the States with PTSD. As he’s closing himself off from his family, his daughter alludes to Grace and Tommy being a better match. Things come to a head, forcing Sam to open up in order to save his marriage. It’s an inversed take on the infidelity film, and the performance from the cast sells it well, with Maguire earning a Golden Globe nomination for one of his best performances.

14 The Great Gatsby (2013)

Baz Luhrmann’s Take On A Classic Infidelity Story

The Great Gatsby (2013)

The Great Gatsby is a 2013 drama romance film based on the book of the same name by F. Scott Fitzgerald. The movie is one of many adaptations of the iconic 1925 novel, this time starring Leonardo DiCaprio as Jay Gatsby and Tobey Maguire as Nick Carraway. The film received a polarizing reception upon release but wontwo Oscars at the 2014 Academy Awards.

Release Date

May 10, 2013

Runtime

143 Minutes

Visionary filmmaker Baz Luhrmann took on one of the most celebrated novels of all time with his adaptation of The Great Gatsby. Set in the 1920s, the movie follows a rich and mysterious man who attempts to reconnect with his old lover who is now married. The movie explores the lives of the rich and morally complex characters of this affluent community which include Jay Gatsby, his former love, Daisy, and her cheating husband Tom.

There are many themes explored in this grand story and an aesthetically pleasing adaptation, but infidelity and its consequences have perhaps the biggest effect on it all. It sets the stage for the famous ending where justice is not necessarily served. The movie is a visually stunning experience and features an all-star cast led by Leonardo DiCaprio as the title character.

13 Bound (1996)

Engrossing Infidelity Thriller Featuring The Mob

Bound

Bound is a 1996 neo-noir crime thriller directed by the Wachowskis. The film stars Gina Gershon and Jennifer Tilly as a pair of women who develop a romantic relationship while conspiring to steal $2 million of mafia money. Joe Pantoliano co-stars as the unsuspecting mafioso boyfriend, creating a tense narrative filled with suspense and intrigue.

Director

Lilly Wachowski , Lana Wachowski

Release Date

October 4, 1996

Cast

Jennifer Tilly , Gina Gershon , Joe Pantoliano , John P. Ryan , Christopher Meloni , Richard C. Sarafian

Runtime

109 Minutes

Before their ground-breaking The Matrix, the Wachowski sisters made their directorial debut with the crime thriller Bound. The film tells the story of an ex-con who meets and falls for the girlfriend of a mob money man. As the two women engage in an affair, they make a plan to steal the money for themselves.

While a much smaller-scale movie than the Wachowskis are known for, it is a gritty and engrossing thriller. However, it also showcases the brilliant filmmaking talent they already possessed. It makes for a sexy and gripping story that has plenty of twists and turns as the audience attempts to figure out who is playing who. While they went on to make a bigger splash with their movies, fans of the Wachowskis should seek out their stunning early work as well.

12 Fish Tank (2009)

Michael Fassbender’s Early Role As A Cheating Boyfriend

Fish Tank

Fish Tank is a British drama directed by Andrea Arnold, focusing on 15-year-old Mia Williams, portrayed by Katie Jarvis. As Mia navigates the challenges of adolescence in a turbulent home environment, her encounter with her mother’s new boyfriend, played by Michael Fassbender, introduces complex dynamics. The film explores themes of frustration and aspiration in a gritty, realistic portrayal of working-class life in contemporary Britain.

Director

Andrea Arnold

Release Date

September 11, 2009

Cast

Katie Jarvis , Michael Fassbender , Kierston Wareing , Rebecca Griffiths , Harry Treadaway , Sydney Mary Nash

Runtime

123 Minutes

Before becoming a household name, Michael Fassbender starred in this small and intense coming-of-age dramaFish Tank. The movie tells the story of a young teenage girl in a lower-class family who struggles with her aggressive and reckless personality while dreaming of becoming a dancer. However, her world is turned upside down when she begins an affair with her mother’s new boyfriend, played by Fassbender.

Anchored by a terrific performance from Katie Jarvis, Fish Tank is a small and impactful story. It explores the coming-of-age drama in a grounded and powerful way, especially when intertwined with themes of infidelity. It can be difficult to watch at times, with Fassebender’s performance being charismatic yet frightening, but makes for a thought-provoking and powerful experience. The small indie movie received critical acclaim and has a Criterion Collection release.

11 Sideways (2004)

Paul Giamatti’s Cheating Friend Creates Moral Conflict

Sideways

Sideways is a 2004 film directed by Alexander Payne, chronicling the road trip of two friends—struggling writer Miles Raymond (Paul Giamatti) and actor Jack Cole (Thomas Haden Church)—through California’s wine country. As they explore vineyards and reflect on their lives, both men confront personal and professional challenges. The film blends humor and drama, providing an in-depth look at friendship and life’s mid-course corrections.

Release Date

October 22, 2004

Director

Alexander Payne

Cast

Jessica Hecht , Marylouise Burke , Thomas Haden Church , Sandra Oh , Virginia Madsen , Paul Giamatti

Runtime

127 minutes

The Oscar-winning comedy Sideways stars Paul Giamatti as a struggling writer who takes his soon-to-be-married friend on a weekend getaway in wine country. However, as the friend looks to find a quick fling before his marriage, Giamatti tries to get up the courage to pursue a friendly waitress. These two very different pursuits collide in hilarious and interesting ways.

The small independent comedy is captivating thanks to its sharp and funny script as well as some wonderful performances from the great cast, including Thomas Hayden Church as the obnoxious, cheating best friend. Like Giamatti’s other collaboration with Alexander Payne, The Holdovers, it is a movie that is funny and touching without ever feeling inauthentic. The movie deals with a lot of topics, including friendship, while also being a story about a midlife crisis which is handled with humor and heartbreak.