11 Movies Like Wonder Boys (2000)

Staff & contributors

Chasing the feel of watching Wonder Boys ? Here are the movies we recommend you watch right after.

Michael Douglas plays Grady Tripp, a craggy, lovable English professor struggling to finish the follow-up to a very successful first novel. It has taken him 7 years, and it's an obvious metaphor for his ridiculous life. The character navigates various tragicomic dilemmas with a stellar supporting cast including Frances McDormand, Tobey Maguire, and Katie Holmes. His editor is Robert Downey Jr. and his nemesis is Rip Torn. Bob Dylan wrote the theme song. How do you not love this movie? It's one of those films that feels like a warm, cozy house (despite the fact that it takes place in a Pittsburgh winter), and it's a great blend of humor and drama.

You know you're in for a treat when you see Julia Louis-Dreyfus and James Gandolfini heading the cast of a sweet and slightly goofy comedy. Steadily going beyond his persona in The Sopranos, you see James Gandolfini playing a role that his fans have probably always imagined him playing: a nice, funny guy with an endearing personality. Directed by Nicole Holofcener, Enough Said almost has a sit-com feel to it: a divorced single parent and masseuse, Eva (Louis-Dreyfus), is looked up by a guy, she briefly met at a party, Albert (Gandolfini). Upon finding out they have much in common, the two start dating. At the same time, she meets Marianne (Catherine Keener), who she becomes friends with and who cannot stop talking ill of her apparently awful ex-husband. You guessed it: it's her new, promising date, Albert. Things get muddy and very funny as she starts to doubt, whether she has made a big mistake. Hilarious, romantic, and smart, it's very much like we expected: a real treat.

Genre: Comedy, Drama, Romance

Actor: Amy Landecker, Anjelah Johnson-Reyes, Barry Jenner, Ben Falcone, Catherine Keener, Christopher Nicholas Smith, Eve Hewson, James Gandolfini, Jessica St. Clair, Julia Louis-Dreyfus, Kathleen Rose Perkins, Lennie Loftin, Luke Grakal, Michaela Watkins, Phillip Brock, Rebecca Drysdale, Rick Irwin, Rob Mayes, Rob Steiner, Sarah Burns, Tavi Gevinson, Toby Huss, Toni Collette, Tracey Fairaway

Director: Nicole Holofcener

Rating: PG-13

Not only is this multi-award-winning drama seriously star-studded, Robert Downey Jr., Rosario Dawson, Channing Tatum, and Shia LaBeouf also deliver superb performances. With two Sundance Awards and many other nominations in its pocket, A Guide to Recognizing Your Saints is based on the eponymous memoir by author, director, and musician, Dito Montiel, who recalls his violent childhood on the mean streets of Queens in the 1980s (LaBeouf plays the young Dito), as he visits his ailing father after 15 years away in Los Angeles (Downey Jr. plays present-day Dito). It is also real-life Dito's directorial debut, recalling the loose, improvisational style of 70s cinema a'la Scorcese. The powerful plot is told through flashbacks and fourth-wall bending monologues, while the eccentric directing style makes for a raw and immediate experience. The energy of this coming-of-age drama is off the charts!

Genre: Crime, Drama

Actor: Adam Scarimbolo, Chance Kelly, Channing Tatum, Chazz Palminteri, Dianne Wiest, Eléonore Hendricks, Eric Roberts, Federico Castelluccio, Gilbert Cruz, Jermel Wilson, Laila Liliana Garro, Martin Compston, Melonie Diaz, Olga Merediz, Peter Anthony Tambakis, Robert Downey Jr., Rosario Dawson, Scott Michael Campbell, Shia LaBeouf

Director: Dito Montiel

Rating: R

Mike Leigh’s forthright and compassionate depiction of working-class life extends to his period pieces as well. Imelda Staunton is remarkable as Vera Drake, a housekeeper in 1950’s London who quietly performs abortions on the side.

Leigh’s vigilant portrayal of class highlights the stark divide between abortion access for the poor and what is offered to the rich. The storytelling is simple and straightforward, he doesn’t over-sentimentalize or grandstand, but merely depicts conditions as they were. Meanwhile, Staunton’s Vera oozes so much fullness, warmth, and empathy, that the heartbreak that follows is mercilessly palpable. 

Genre: Drama

Actor: Adrian Scarborough, Alan Williams, Alex Kelly, Allan Corduner, Angela Curran, Anna Keaveney, Anthony O'Donnell, Billie Cook, Billy Seymour, Chris O'Dowd, Craig Conway, Daniel Mays, Eddie Marsan, Eileen Davies, Elizabeth Berrington, Emma Amos, Fenella Woolgar, Gerard Monaco, Heather Craney, Helen Coker, Imelda Staunton, Jake Wood, James Payton, Jane Wood, Jeffry Wickham, Jim Broadbent, Joanna Griffiths, John Warman, Leo Bill, Lesley Manville, Lesley Sharp, Liz White, Marion Bailey, Martin Savage, Nicholas Jones, Nicky Henson, Paul Jesson, Paul Raffield, Peter Wight, Phil Davis, Richard Graham, Robert Putt, Rosie Cavaliero, Ruth Sheen, Sally Hawkins, Sam Troughton, Sandra Voe, Sid Mitchell, Simon Chandler, Sinéad Matthews, Tilly Vosburgh, Tom Ellis, Vincent Franklin, Vinette Robinson, Wendy Nottingham

Director: Mike Leigh

Rating: R

Starring Matthew Broderick and a young Reese Witherspoon as, respectively, Jim McAllister, a high school teacher and Tracy Flick, a notorious 'that girl' in his class. When Tracy decides to run for class president, we see the floodgates open as all sorts of bizarre and insane behavior pours out of the two. Quickly, it becomes clear that Tracy will do nearly anything to win, and as circumstances spiral out of control, madness descends - along with hilarity!

Genre: Comedy, Drama, Mystery, Romance

Actor: B.J. Tobin, Chris Klein, Colleen Camp, Delaney Driscoll, Frankie Ingrassia, Holmes Osborne, Jason Paige, Jeanine Jackson, Jessica Campbell, Jillian Crane, John Ponzio, Kaitlin Ferrell, Marilyn Tipp, Mark Harelik, Matt Golden, Matt Malloy, Matthew Broderick, Molly Hagan, Nicholas D'Agosto, Phil Reeves, Reese Witherspoon, Rohan Quine

Director: Alexander Payne

Rating: R

Paul Giamatti knocks in out of the park in Win Win. The movie has so much humanity in it as well as a fantastic story that's rooted in normalcy. At last a movie about second chances that is anything but cheesy. The rhythm of the humor in this movie helps you move through the serious themes unscathed (for the most part). In sum, the jokes are spot-on and the acting is excellent.

Genre: Comedy, Drama, Family

Actor: Alex Shaffer, Amy Ryan, Bobby Cannavale, Burt Young, Clare Foley, Darren Goldstein, David W. Thompson, Edmund Ikeda, Jeffrey Tambor, Marceline Hugot, Marcia Haufrecht, Margo Martindale, Melanie Lynskey, Nina Arianda, Paul Giamatti, Sharon Wilkins, Tim Ransom

Director: Tom McCarthy

Rating: R

Happy-Go-Lucky is a Mike Leigh feel-good movie tells the story of Poppy, a North London teacher, whose story we follow through a number of different situations: driving lessons, solving work issues, having fun with friends, all while trying not to lose her optimism. The acting is superb, Sally Hawkins is a gem as Poppy, and one cannot describe it, one simply has to see it and enjoy it, because it leaves you smiling :)

Genre: Comedy, Drama, Romance

Actor: Alexis Zegerman, Andrea Riseborough, Caroline Martin, Eddie Marsan, Elliot Cowan, Joseph Kloska, Karina Fernandez, Kate OFlynn, Nonso Anozie, Oliver Maltman, Philip Arditti, Rebekah Staton, Sally Hawkins, Samuel Roukin, Sarah Niles, Sinéad Matthews, Stanley Townsend, Sylvestra Le Touzel, Trevor Cooper, Viss Elliot Safavi

Director: Mike Leigh

Rating: R

Lee Holloway (Maggie Gyllenhaal) is compassionate and diminutive, but her social awkwardness hinders her as she attempts to navigate young adulthood. After recently being hospitalized for self-harm, Lee is determined to prove she is capable of autonomously taking care of herself. She begins working as a secretary for E. Edward Grey (James Spader), a meticulous attorney.

It’s not long before both Lee and Edward realize they’re attracted to one another’s opposite natures: Lee’s obedience and Edward’s dominance. They begin a mutually consensual BDSM relationship, with both experiencing a sexual and emotional awakening. 

The premise may sound familiar: 50 Shades of Grey is widely acknowledged as, at the very least, owing its title to Secretary. But while 50 Shades of Grey portrays an unhealthy, toxic, and superficial idea of a BDSM affair, Secretary maintains that consent must be at the core of any relationship. And ultimately for Lee and Edward, BDSM becomes a way for them to communicate and overcome their individual pain, and unite stronger as a vulnerable, loving whole.

Genre: Comedy, Drama, Romance

Actor: Alison Tatlock, Amy Locane, Christina Gray, Ezra Buzzington, Herbert Russell, James Spader, Jeremy Davies, Jessica Tuck, Julene Renee, Kyle Colerider-Krugh, Lacey Kohl, Lauren Cohn, Lesley Ann Warren, Lily Knight, Maggie Gyllenhaal, Mary Joy, Michael Mantell, Osgood Perkins, Oz Perkins, Patrick Bauchau, Sabrina Grdevich, Stephen McHattie, Steven Fierberg, Steven Shainberg

Director: Steven Shainberg

Rating: R

Philipp Seymour Hoffman stars in this family drama next to Laura Linney as siblings. They have to unite to support their father who after the death of his girlfriend finds himself alone. The Savages, after the family name, have dynamics that are all too common and easily recognizable. This is a beautiful and real movie.

Genre: Drama

Actor: Cara Seymour, David Zayas, Debra Monk, Erica Berg, Gbenga Akinnagbe, Guy Boyd, Jennifer Lim, Joan Jaffe, Laura Linney, Maddie Corman, Margo Martindale, Michael Blackson, Peter Frechette, Peter Friedman, Philip Bosco, Philip Seymour Hoffman, Rosemary Murphy, Sage Kirkpatrick, Salem Ludwig, Sandra Daley, Sidné Anderson, Tonye Patano, Zoe Kazan

Director: Tamara Jenkins

Rating: R

Based on the comic book by Daniel Clowes, Ghost World is a dark comedy that follows the exploits of teenage outcasts Enid and Rebecca (Thora Birch and Scarlett Johansson) as they navigate the many complexities of burgeoning adulthood. Central to the story is the unlikely friendship that Enid strikes up with a lonesome older man (played by Steve Buscemi), a curious relationship that drifts through various humorous and melancholy situations. It’s an original and often poignant look at alienation and identity, with Birch delivering a wonderfully deadpan and often hilarious performance, despite her entirely pessimistic attitude. It’s the type of film that’s just right when you’re in the mood for something just a little bit different.

Genre: Comedy, Drama

Actor: Alex Solowitz, Anna Berger, Ashley Peldon, Bob Balaban, Brad Renfro, Brett Gilbert, Brian George, Bruce Glover, Chachi Pittman, Charles C. Stevenson Jr., Charles Schneider, Daniel Graves, Dave Sheridan, David Cross, Debi Derryberry, Debra Azar, Diane Salinger, Ezra Buzzington, Illeana Douglas, Jake La Botz, James Sie, Jerry Rector, Joan Blair, Joel Michaely, John Bunnell, Joseph Sikora, Joy Bisco, Kaileigh Brielle Martin, Lauren Bowles, Lindsey Girardot, Lorna Scott, Marc Vann, Martin Grey, Matt Doherty, Pat Healy, Patrick Fischler, Paul Keith, Rini Bell, Scarlett Johansson, Sid Hillman, Stacey Travis, Steve Buscemi, T. J. Thyne, Teri Garr, Thora Birch, Tom McGowan, Venus DeMilo Thomas, Will Forte

Director: Terry Zwigoff

Rating: R

Set during the swingin' seventies, two small town Connecticut families are the subject of this visually stunning and somewhat disturbing drama. With an all-star cast that includes Sigourney Weaver as Janey Carver, an unsatisfied housewife and mother of two and Elijah Wood as her eldest son, there's plenty of star power and drama. In addition, director Ang Lee brings his signature sense of trial and unease while unleashing a quirky and pointed 70's aesthetic.

Genre: Drama

Actor: Adam Hann-Byrd, Allison Janney, Barbara Garrick, Bettina Skye, Byron Jennings, Christina Ricci, Christine Farrell, Colette Kilroy, Colleen Camp, Courtney Peldon, Daniel McDonald, David Krumholtz, Dennis Gagomiros, Donna Mitchell, Elijah Wood, Glenn Fitzgerald, Henry Czerny, Ivan Kronenfeld, Jamey Sheridan, Jessica Stone, Joan Allen, Joe O'Connor, John Benjamin Hickey, Jonathan Freeman, Kate Burton, Katie Holmes, Kevin Kline, Larry Pine, Maia Danziger, Marcell Rosenblatt, Michael Cumpsty, Miles Marek, Nancy Opel, Robert Westenberg, Sarah Thompson, Scott Wentworth, Sigourney Weaver, Tobey Maguire, William Cain

Director: Ang Lee

Rating: R

With an ensemble cast featuring a young Natalie Portman and a less murderous Uma Thurman, Ted Demme's "Beautiful Girls" recreates the worries and woes that thrive in the minds of a tight knit group of working class friends stuck in their own small town Massachusetts world. Warm, quirky and filled with champagne diamonds, both metaphorical and tangible, for anybody who's ever walked the thirty something walk, it's a film that'll make you want to remember all the friends you wish you still had and actually still do.

Genre: Comedy, Drama, Romance

Actor: Adam LeFevre, Annabeth Gish, Anne Bobby, David Arquette, Frank Anello, John Carroll Lynch, John Scurti, Lauren Holly, Martha Plimpton, Matt Dillon, Max Perlich, Michael Rapaport, Mira Sorvino, Natalie Portman, Noah Emmerich, Pruitt Taylor Vince, Rachel Oliva, Richard Bright, Rosie O'Donnell, Sam Robards, Timothy Hutton, Tomas Settell, Uma Thurman

Director: Ted Demme

Rating: R