Best movies like Wonder Boys

Undependable. Unpredictable. Unforgettable.

A unique, carefully handpicked, selection of the best movies like Wonder Boys Starring Michael Douglas, Tobey Maguire, Frances McDormand, Robert Downey Jr., and more. If you liked Wonder Boys then you may also like: You Will Meet a Tall Dark Stranger, Your Friends & Neighbors, Naked in New York, The Opposite of Sex, Kicking and Screaming and many more popular movies featured on this list. You can further filter the list even more or get a random selection from the list of similar movies, to make your selection even easier.

movie

Grady is a 50-ish English professor who hasn't had a thing published in years—not since he wrote his award winning 'Great American Novel' 7 years ago. This weekend proves even worse than he could imagine as he finds himself reeling from one misadventure to another in the company of a new wonder boy author.

selected filters: Sort: Default

You may filter the list of movies on this page for a more refined, personalized selection of movies.

Still not sure what to watch click the recommend buttun below to get a movie recommendation selected from all the movies on this list

Know any good movies to watch like Wonder Boys 2000. With a similar plot or stoyline. Suggest it.

You Will Meet a Tall Dark Stranger

Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.

Your Friends & Neighbors

This adult comedy follows six characters, three men and three women from a cross-section of social groups, as they play sexual power games. When an affair fires up between 2 of the married characters, it sparks a chain of consequences for all of them, including one of the wives falling for another woman!

Naked in New York

Naked in New York begins in the car of grown up Jake, he is talking to us about his girlfriend, Joanne, and to whom you can turn to for help while facing life. From there it flashes back to his memories of his parents, college, house across from a squirrel infested peanut factory, best friend, writing career and Joanne.

The Opposite of Sex

A 16-year-old girl visits her gay half-brother and ends up seducing his boyfriend, thus wreaking havoc on all of their lives.

Kicking and Screaming

After college graduation, Grover's girlfriend Jane tells him she's moving to Prague to study writing. Grover declines to accompany her, deciding instead to move in with several friends, all of whom can't quite work up the inertia to escape their university's pull. Nobody wants to make any big decisions that would radically alter his life, yet none of them wants to end up like Chet, the professional student who tends bar and is in his tenth year of university studies.

Accident

Stephen is a professor at Oxford University who is caught in a rut and feels trapped by his life in both academia and marriage. One of his students, William, is engaged to the beautiful Anna, and Stephen becomes enamored of the younger woman. These three people become linked together by a horrible car crash, with flashbacks providing details into the lives of each person and their connection to the others in this brooding English drama.

Brad's Status

Although Brad has a satisfying career, a sweet wife and a comfortable life in suburban Sacramento, things aren't quite what he imagined during his college glory days. When he accompanies his musical prodigy son on a university tour, he can't help comparing his life with those of his four best college friends who seemingly have more wealthy and glamorous lives. But when circumstances force him to reconnect with his former friends, Brad begins to question whether he has really failed or if their lives are actually more flawed than they appear.

P.S.

Louise, an unfulfilled divorced woman with regrets, gets the chance to relive her past when she meets a young man who bears an uncanny resemblance, in name and appearance, to her high school sweetheart who died many years before.

Adaptation.

Nicolas Cage is Charlie Kaufman, a confused L.A. screenwriter overwhelmed by feelings of inadequacy, sexual frustration, self-loathing, and by the screenwriting ambitions of his freeloading twin brother Donald. While struggling to adapt "The Orchid Thief," by Susan Orlean, Kaufman's life spins from pathetic to bizarre. The lives of Kaufman, Orlean's book, become strangely intertwined as each one's search for passion collides with the others'.

A Serious Man

It is 1967, and Larry Gopnik, a physics professor at a quiet Midwestern university, has just been informed by his wife Judith that she is leaving him. She has fallen in love with one of his more pompous acquaintances Sy Ableman.

The History Boys

The story of an unruly class of bright, funny history students at a Yorkshire grammar school in pursuit of an undergraduate place at Oxford or Cambridge. Bounced between their maverick English master, a young and shrewd teacher hired to up their test scores, a grossly out-numbered history teacher, and a headmaster obsessed with results, the boys attempt to pass.

Educating Rita

Rita, a witty 26-year-old hairdresser, wants to 'discover' herself, so she joins the Open University where she meets the disillusioned professor of literature, Dr. Frank Bryant. His marriage has failed, his new girlfriend is having an affair with his best friend and he can't get through the day without downing a bottle or two of whisky. What Frank needs is a challenge... and along comes Rita.

The Decline of the American Empire

Four very different Montreal university teachers gather at a rambling country house to prepare a dinner. Remy (married), Claude (a homosexual), Pierre (involved with a girlfriend) and Alain (a bachelor) discuss sex, the female body and their affairs with them. Meanwhile, their four female guests, Louise (Remy's wife of 15 years), Dominique (a spinster), Diane (a divorcée) and Danielle (Pierre's girlfriend) are spending the time at a downtown health gym. They also discuss sex, the female body and, naturally, men. Later in the evening, they finally meet at the country house and have dinner. A ninth guest, named Mario, who used to know Diane, drops in on the group for some talk and has a surprise of his own.

Match

A Seattle couple travel to New York to interview colorful former dancer Tobi for research on a dissertation about dance. But soon, common niceties and social graces erode when the questions turn personal and the true nature of the interview is called into question.

Happy Birthday, Gemini

Based on the off-Broadway/Broadway smash of the 1970s; a poor Harvard student's romance with a girl hits a rough spot when he realizes, on his 21st birthday, that he may be in love with her brother.

The Perks of Being a Wallflower

Pittsburgh, Pennsylvania, 1991. High school freshman Charlie is a wallflower, always watching life from the sidelines, until two senior students, Sam and her stepbrother Patrick, become his mentors, helping him discover the joys of friendship, music and love.

Sideways

Two middle-aged men embark on a spiritual journey through Californian wine country. One is an unpublished novelist suffering from depression, and the other is only days away from walking down the aisle.

Finding Forrester

Gus Van Sant tells the story of a young African American man named Jamal who confronts his talents while living on the streets of the Bronx. He accidentally runs into an old writer named Forrester who discovers his passion for writing. With help from his new mentor Jamal receives a scholarship to a private school.

Happy Together

Christopher is an ambitious college freshman, striving to become a writer. Through a computer fault he's assigned the same room as Alex, a real party freak and... a girl! He's annoyed and tries to get a different room as soon as possible, but when he learns to know her, he also starts to like her. She not only improves his sexual life, but also his writing skills

Last Wedding

Three couples in Vancouver navigate their relationships: first jobs, first crises, professional jealousy, an affair, and lack of communication. Noah and Zipporah marry after a brief courtship. She wants to be a singer and stalls out when she fails. He's working hard at a business that may go under. Sarah and Shane are architects; he can't handle her success at a downtown firm. Leslie is a librarian, sour and prickly; her mate, Peter, is a college teacher whose head is turned by a student. Can any of these couples sort things out and stay together? Should they?

Story of a Bad Boy

17 year old Pauly is a closeted high school kid who wants it all. His dad wants him to make the track team, his mom wants him to do well in band, and Pauly just wants to get closer to the new student teacher doing the school play.

House

Fresh from group therapy, a man shares odd anecdotes with ten others inside a church.

Husbands and Wives

When Jack and Sally announce that they're splitting up, this comes as a shock to their best friends Gabe and Judy. Maybe mostly because they also are drifting apart and are now being made aware of it. So while Jack and Sally try to go on and meet new people, the marriage of Gabe and Judy gets more and more strained, and they begin to find themselves being attracted to other people.

Live Nude Girls

A group of old friends at a Hens Night discuss their issues, uncertainties, fears and fantasies.

Lovelife

Lovelife is a 1997 romantic comedy film written and directed by Jon Harmon Feldman. The ensemble cast includes Matt Letscher, Sherilyn Fenn, Saffron Burrows, Carla Gugino, Bruce Davison, Jon Tenney and Peter Krause. Lovelife was nominated for a Feature Film Award at the 1997 Austin Film Festival, and won an Audience Award at the Los Angeles Independent Film Festival. The film was winner of the screenplay award at the L.A. Indie fest.

5.5 / 10 1992 Comedy
suggested by: user2697vhmsecd

Monster in a Box

This is the story of Spalding Gray and his attempt to write a novel. It is a first person account about writing and living, and dealing with success while trying to be successful.

P.S. Your Cat Is Dead!

With his life already in shambles -- his girlfriend just dumped him, he's lost his acting gig, and his cat is seriously ill -- sad-sack Jimmy Zoole (Steve Guttenberg) comes home New Year's Eve to find a gay burglar (Lombardo Boyar) looting his apartment. Taking the intruder hostage, Jimmy threatens to unleash his pent-up rage on the would-be thief but instead begins to bond with his captive.

Paper Man

A coming-of-middle-age comedy that chronicles the unlikely friendship between failed author Richard Dunne and a Long Island teen who teaches him a thing or two about growing up, all under the disapproving eye of his long-suffering wife and his imaginary Superhero friend.

6.8 / 10 2007 Drama
suggested by: ThunderTiger

The Savages

A sister and brother face the realities of familial responsibility as they begin to care for their ailing father.

Sleep with Me

Six different writers wrote a scene each of this romantic comedy featuring the marriage and turbulent relationship of Joseph and Sarah, with Joseph's best friend Frank trying hard to cope with letting the love of his life marry his best friend.

Smart People

Professor Lawrence Wetherhold might be imperiously brilliant, monumentally self-possessed and an intellectual giant -- but when it comes to solving the conundrums of love and family, he's as downright flummoxed as the next guy.

The Squid and the Whale

Based on the true childhood experiences of Noah Baumbach and his brother, The Squid and the Whale tells the touching story of two young boys dealing with their parents' divorce in Brooklyn in the 1980s.

Storytelling

College and high school serve as the backdrop for two stories about dysfunction and personal turmoil.

The Trip

When 19-year-old gay-rights activist Tommy and 24-year-old Alan first meet in 1973, they find themselves on the opposite sides of the political coin...

You Hurt My Feelings

A novelist's longstanding marriage is suddenly upended when she overhears her husband giving his honest reaction to her latest book.

Oleanna

Carol, a college student, comes to John's office, her professor, to discuss the grade she has received for one of her papers.

I Used to Go Here

Following the launch of her new novel, 35-year-old writer Kate Conklin is invited to speak at her alma mater by her mentor and former professor. After accepting the invitation, Kate finds herself deeply enmeshed in the lives of an eccentric group of college students.

Ellie Parker

Ellie Parker, an aspiring actress from Australia, lives a hectic Hollywood lifestyle, perpetually trying to land the role that will elevate her career. Living with her lothario musician boyfriend, Justin, Ellie is far from happy, finding support primarily from her friend Sam. But when Ellie meets Chris after a minor traffic accident, she sees new potential for both romance and her life in general.

The Misadventures of Margaret

A timid, insecure popular author with an overly-attentive professor husband decide to write an erotic novel. With encouragement from her sister and a bi-sexual friend, she goes to France with the intent of doing research at an inn where a diary she had been using documented erotic encounters. Instead she finds the inn is now a cloister for singing nuns. However, a young, divorced sound engineer is also there taping the nuns. While attracted, she mostly succumbs only to new fantasies until he follows her home to New York.

Submission

A well-respected professor who is a celebrated novelist and loving husband loses himself when he becomes obsessed with an ambitious and talented student.

People, Places, Things

Will Henry is a newly single graphic novelist balancing being a parent to his young twin daughters and teaching a classroom full of college students, all the while trying to navigate the rich complexities of new love and letting go of the woman who left him.

Starting Out in the Evening

Leonard Schiller once counted among New York's literary lions, but illness and ten years of writer's block have lowered his profile, almost to the point of obscurity. When Heather Wolfe, an ambitious literature major, asks to interview him for her thesis on his work, her interest forces him to address the issues that he has avoided all these years, and stirs in him feelings he has long forgotten, much to his daughter's consternation.

Butley

Butley is set in Queen Mary’s College, London and focuses on two English instructors, Ben Butley, a middle-aged former T. S. Eliot expert whose life is now in a shambles, and his protégé, Joey, a homosexual. With both Joey and his wife leaving, Butley faces a life alone, fighting back with wit, obscenity and booze.

My Teacher's Wife

Todd Boomer is a college student aspiring to get into University. His chances are looking poor when his maths teacher, fails him in every maths test. Help arrives in the guise of the gorgeous Vicki, a mathematical genius who decides to tutor Todd. As the relationship develops,Todd finds himself in an affair with Vicki unknowing of her marriage to his math teacher.

American Crude

Quite a bit can happen over the course of a single day in L.A., and when smooth-talking scam artist Johnny decides to throw a bachelor party for his best friend Bill the events of the day take a bizarre turn. As the festivities get underway, the appearance of a transvestite prostitute, a trigger-happy ex-con, and a notorious porn king signal that this isn't going to be a typical night out.

Gurov & Anna

With his marriage to Audrey almost at an end, Ben begins a torrid affair with Mercedes, a young French student in his writing class. The affair soon spins out of control, their emotions and Ben and Audrey's family hanging in the balance.

Beat

The true story of two murders that shaped the lives of several college students who went on to become some of the most influential writers of the "Beat Generation."

Trailer Park Boys: Countdown to Liquor Day

Ricky, Julian and Bubbles are about to get out of jail, and this time, Julian vows to go straight, even open a legit business. Soon the Boys will all be rich. At least that's what they've told the parole board. But when they arrive back at the park, they find it's not the same old Sunnyvale - and it's not the same old Jim Lahey, Trailer Park Supervisor.

Late Last Night

After a fight with his wife, who's leaving him, Dan's day is getting worse by the minute. He calls an old friend for a night of binge drinking and intoxication. They start a cathartic ride through the city's underbelly.

How to Be

A young man having an existential crisis convinces a Canadian self-help guru to come to London and become his personal life coach.

More related lists

Sort results by:

X close
Default
Clear filters
...