20 best movies like Wonder Boys (2000)

Tracy, a lonely college freshman in New York, is rescued from her solitude by her soon-to-be stepsister Brooke, an adventurous gal about town who entangles her in alluringly mad schemes. Mistress America is a comedy about dream-chasing, score-settling, makeshift families, and cat-stealing.

Anger rages in Philip as he awaits the publication of his second novel. He feels pushed out of his adopted home city by the constant crowds and noise, a deteriorating relationship with his photographer girlfriend Ashley, and his own indifference to promoting the novel. When Philip's idol Ike Zimmerman offers his isolated summer home as a refuge, he finally gets the peace and quiet to focus on his favorite subject: himself.

A couple's visit with their son takes a dramatic turn when the father tells him he plans on leaving his mother.

Erik, a lecturer in architecture, inherits his father’s large old house in Hellerup, north of Copenhagen. His wife Anna, a well-known television newscaster, suggests that they invite their friends to come and live with them. In this way she hopes to evade the boredom that has begun to seep into their marriage. Before long, a dozen women, men and children move into the country house, make collective decisions, engage in discussions and go swimming together in the nearby Øresund strait. They also rub each other up the wrong way on account of their smaller and larger idiosyncrasies. Their fragile equilibrium threatens to come undone when Erik falls in love with his student Emma and the young woman moves into the house. Fourteen-year-old Freja, daughter of Erik and Anna, aloofly observes these goings-on and seeks her own way.

Calvin is a young novelist who achieved phenomenal success early in his career but is now struggling with his writing – as well as his romantic life. Finally, he makes a breakthrough and creates a character named Ruby who inspires him. When Calvin finds Ruby, in the flesh, sitting on his couch about a week later, he is completely flabbergasted that his words have turned into a living, breathing person.

Desperate to be rid of her toddler, a dissatisfied Beverly Hills housewife hires a stranger to babysit and ends up getting much more than she bargained for.

The film tells the story of quick-witted teen Mark, contentedly living the same day in an endless loop whose world is turned upside-down when he meets mysterious Margaret also stuck in the time loop. Mark and Margaret form a magnetic partnership, setting out to find all the tiny things that make that one day perfect. What follows is a love story with a fantastical twist, as the two struggle to figure out how -- and whether -- to escape their never-ending day.

Married couple Jack and Terry Linden are experiencing a difficult period in their relationship. When Jack decides to step outside the marriage, he becomes involved with Edith, who happens to be the wife of his best friend and colleague, Hank Evans. Learning of their partners' infidelity, Terry and Hank engage in their own extramarital affair together. Now, both marriages and friendships are on the brink of collapse.

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.

When new kid in town Ed Wallis is given an assignment to interview an older person, he turns to his mysterious neighbor, Ashby Holt for help. That new connection leads to unexpected journeys for both of them, as Ashby – who turns out to be a retired CIA assassin – deals with a terminal prognosis, and Ed deals with adjusting to life with his newly single mom and developing relationship with a brainy classmate, Eloise.

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.

Greg is coasting through senior year of high school as anonymously as possible, avoiding social interactions like the plague while secretly making spirited, bizarre films with Earl, his only friend. But both his anonymity and friendship threaten to unravel when his mother forces him to befriend a classmate with leukemia.

Famous and wealthy funnyman George Simmons doesn't give much thought to how he treats people until a doctor delivers stunning health news, forcing George to reevaluate his priorities with a little help from aspiring stand-up comic Ira.

The story of Florence Foster Jenkins, a New York heiress, who dreamed of becoming an opera singer, despite having a terrible singing voice.

Ishaan Awasthi is an eight-year-old whose world is filled with wonders that no one else seems to appreciate. Colours, fish, dogs, and kites don't seem important to the adults, who are much more interested in things like homework, marks, and neatness. Ishaan cannot seem to get anything right in class; he is then sent to boarding school, where his life changes forever.

A boy meets a girl named Riya and falls in love. After struggling to convince her to be his girlfriend, she half-heartedly agrees to be his `half-girlfriend'.

Savannah is the true story of Ward Allen, a romantic and bombastic character who rejects his plantation heritage for the freedom of life on a river. Ward navigates the change of early 20th century America on the wrong side of the law and society, his long-time friend, a freed slave named Christmas Moultrie, at his side. Master of Shakespeare, and the shotgun that provides Savannah's markets with fowl, Ward fights for his rights as a hunter. His charisma and eloquent rhetoric win the heart of a society woman who defies her father to marry him. An elderly Moultrie tells the story of life on the river with his friend to a little boy, who passes the legendary Ward Allen down to the next generation.

Terri, a pajama-clad, disaffected high school student learns how to engage the world with the help of Mr. Fitzgerald, his assistant principal.

Amy, a naive college graduate who believes she's destined to be a great poet, begrudgingly accepts a job at a sex shop while she pursues a mentorship with reclusive writer Rat Billings.

THE EXTRA MAN is a sophisticated and moving comedy from filmmakers Shari Springer Berman and Robert Pulcini. THE EXTRA MAN follows Louis Ives (Paul Dano), a lonely dreamer who fancies himself the hero of an F. Scott Fitzgerald novel. When a deeply embarrassing incident forces him to leave his job at an exclusive Princeton prep school, Louis heads to New York City to make a fresh start. He quickly finds a 9 to 5 job at an environmental magazine, where he encounters an entrancing, green-obsessed co-worker Mary (Katie Holmes).

Ivy League Freshman, Aaron Milton (17) gets a different kind of education when he falls for Linda (34) a vivacious former wild-child who has returned to college to straighten out her life. The curriculum gets more challenging when Aaron meets Linda's sarcastic 14 year-old daughter, Beth - who quickly develops a crush on him. The math doesn't work in either direction but the dysfunctional triangle becomes a learning experience for all involved.

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.

Growing up in a rural town filled with violent delinquents, Jack has learned to do what it takes to survive, despite having an oblivious mother and no father. After his aunt falls ill and a younger cousin comes to stay with him, the hardened 15-year-old discovers the importance of friendship, family, and looking for happiness even in the most desolate of circumstances.

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.

After learning that his terminally ill wife has six months to live, a man welcomes the support of his best friend who moves into their home to help out.

In the not so distant future, Theodore, a lonely writer purchases a newly developed operating system designed to meet the user's every needs. To Theodore's surprise, a romantic relationship develops between him and his operating system. This unconventional love story blends science fiction and romance in a sweet tale that explores the nature of love and the ways that technology isolates and connects us all.

Over the course of his summer break, a teenager comes into his own thanks in part to the friendship he strikes up with one of the park's managers.

A girl, abandoned by her mother when she was three, moves to a small town in Florida with her father. There, she adopts an orphaned dog she names Winn-Dixie. The bond between the girl and her special companion brings together the people in a small Florida town and heals her own troubled relationship with her father.

A boy, obsessed with comparing himself with those less fortunate, experiences a different life at the home of his aunt and uncle in 1959 Sweden.

A man struggles with the tragic memories of his past to make sense of his present, but soon realizes that time isn't the enemy he thinks it is.

When a beautiful first-grade teacher arrives at a prep school, she soon attracts the attention of an ambitious teenager named Max, who quickly falls in love with her. Max turns to the father of two of his schoolmates for advice on how to woo the teacher. However, the situation soon gets complicated when Max's new friend becomes involved with her, setting the two pals against one another in a war for her attention.

Jake and Kristy Briggs are newlyweds. Being young, they are perhaps a bit unprepared for the full reality of marriage and all that it (and their parents) expect from them. Do they want babies? Their parents certainly want them to. Is married life all that there is? Things certainly aren't helped by Jake's friend Davis, who always seems to turn up just in time to put a spanner in the works.

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.

In the city of New York, comedian Alvy Singer falls in love with the ditsy Annie Hall.

Magali, forty-something, is a winemaker and a widow: she loves her work but feels lonely. Her friends Rosine and Isabelle both want secretly to find a husband for Magali.

Eva is a divorced soon-to-be empty-nester wondering about her next act. Then she meets Marianne, the embodiment of her perfect self. Armed with a restored outlook on being middle-aged and single, Eva decides to take a chance on her new love interest Albert — a sweet, funny and like-minded man. But things get complicated when Eva discovers that Albert is in fact the dreaded ex–husband of Marianne...

Dumped by her husband, longtime housewife Deanna turns regret into reset by going back to college. Winding up at the same school as her daughter, Deanna plunges headlong into the campus experience – embracing fun, freedom and frat boys.

Set in New York City in the sweltering summer, The Wackness tells the story of a troubled teenage drug dealer, who trades pot for therapy sessions with a drug-addled psychiatrist. Things get more complicated when he falls for one of his classmates, who just happens to be the doctors daughter. This is a coming-of-age story about sex, drugs, music and what it takes to be a man.

During their travels from Chicago to New York, Harry and Sally Will debate whether or not sex ruins a perfect relationship between a man and a woman. Eleven years later, and they're still no closer to finding the answer.

Charlie Simms is a student at a private preparatory school who comes from a poor family. To earn the money for his flight home to Gresham, Oregon for Christmas, Charlie takes a job over Thanksgiving looking after retired U.S. Army officer Lieutenant Colonel Frank Slade, a cantankerous middle-aged man who lives with his niece and her family.

Santiago, capital of Chile during the Marxist government of elected, highly controversial president Salvador Allende. Father McEnroe supports his leftist views by introducing a program at the prestigious "collegio" (Catholic prep school) St. Patrick to allow free admission of some proletarian kids. One of them is Pedro Machuca, slum-raised son of the cleaning lady in Gonzalo Infante's liberal-bourgeois home. Yet the new classmates become buddies, paradoxically protesting together as Gonzalo gets adopted by Pedro's slum family and gang. But the adults spoil that too, not in the least when general Pinochet's coup ousts Allende, and supporters such as McEnroe.

After a breakup with her boyfriend, a young woman moves in with her older brother, his wife, and their 2-year-old son.

An inner-city high school teacher discovers she is pregnant at the same time as one of her most promising students and the two develop an unlikely friendship while struggling to navigate their unexpected pregnancies.

An uptight documentary filmmaker and his wife find their lives loosened up a bit after befriending a free-spirited younger couple.

Romantic comedy about six of Seattle's young people, most of whom live in the same apartment building and whose lives revolve around the city's ever-expanding music scene. The interrelated stories about each character's progress through the singles scene are intriguing and often very funny, and the soundtrack is a grunge fanatic's dream, with the likes of Soundgarden, Pearl Jam and Mudhoney.

Soon-to-be-wed graduate student Finn Dodd develops cold feet when she suspects her fiancé is cheating on her. In order to clear her head, Finn visits her grandmother, Hy, and great aunt, Glady Joe Cleary, in Grasse, Calif. There, Finn learns that Hy and Glady Joe are members of a group of passionate quilters, and over the course of her visit she is regaled with tales of love and life by women who have collected rich experiences and much wisdom.

This story concerns a hapless civil servant who gets more than he bargains for when he moves into an apartment in Limerick with a gay fashion student and becomes a star on the catwalk. A contemporary story embracing the essence of what it is to be young in today's Ireland.

While holidaying in the French Alps, a Swedish family deals with acts of cowardliness as an avalanche breaks out.

All but abandoned by her family in a London retirement hotel, an elderly woman strikes up a curious friendship with a young writer.

After spending two decades in England, Bill Bryson returns to the U.S., where he decides the best way to connect with his homeland is to hike the Appalachian Trail with one of his oldest friends.