7 Movies Like Sideways (2004) On Max (HBO Max)

Staff & contributors

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

Best friends Miles and Jack are off to wine country to celebrate Jack's last week of freedom before he gets married. They drop white lies about themselves, with Miles pretending to be a successful writer and Jack not mentioning his impending wedding, and soon meet two beautiful women whom they spend the rest of their stay with. What sounds like a dreamy bachelor's celebration, however, soon unravels into a messy tangle of tall tales. Miles and Jack contemplate their situation in smart, sad, and silly turns, delivering excellent performances and an overall hard-hitting road movie. 

Directed by David Cronenberg, Eastern Promises is at times brutal—such is the famous Canadian director's trademark—and operates at a fever pitch of grim violence and revenge. Starring a tattooed, ruthless, and terrifying Viggo Mortensen as a very convincing Russian strong-arm gangster as well as Naomi Watts and Vincent Cassel, it features intense psychological drama and a gritty crime story. Midwife Anna (Watts) delivers the baby of a 14-year-old Russian prostitute, who dies while giving birth, and later learns that she was forced into prostitution by the Mafia. To keep this knowledge from seeping out, she gets entangled deeper into London's criminal underbelly, whose various factions and languages are aptly showcased by Cronenberg. Add to all this a smart script and Mortensen's daring performance and you have yourself an intense auteur thriller in signature Cronenberg style.

Genre: Crime, Drama, Mystery, Thriller

Actor: Aleksandar Mikic, Aleksander Mikic, Alice Henley, Armin Mueller-Stahl, David Papava, Donald Sumpter, Elisa Lasowski, Jerzy Skolimowski, Josef Altin, Mina E. Mina, Naomi Watts, Raza Jaffrey, Sarah-Jeanne Labrosse, Sinead Cusack, Tamer Hassan, Tatiana Maslany, Tereza Srbová, Tony Cook, Viggo Mortensen, Vincent Cassel

Director: David Cronenberg

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, Romance

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

Director: Alexander Payne

Rating: R

We all love Jeff Bridges. We all agree that we shouldn't leave a movie he won an Oscar for unwatched. That's enough reason to watch this movie, but there are so many others. The story is fantastic and based on true events: a country musician living rough and having a shot at happiness after he falls for a journalist who interviews him. The score is composed by T Bone Burnett. The journalist is played by Maggie Gyllenhaal and another musician is played by Colin Farrell. So many reasons to watch.

Genre: Drama, Music, Romance

Actor: Beth Grant, Brian Gleason, Chad Brummett, Colin Farrell, David Manzanares, Debrianna Mansini, Harry Zinn, J. Michael Oliva, James Keane, Jeff Bridges, Josh Berry, Maggie Gyllenhaal, Paul Herman, Rick Dial, Robert Duvall, Ryan Bingham, Tom Bower, William Marquez, William Sterchi

Director: Scott Cooper

Rating: R

A young girl is looking for her father while struggling to care for her family. The film is bleak and slow but great performances from the cast, especially the lead, will keep you engaged throughout. The story has a very real, raw, and natural feeling to it, so natural in fact that at times, you will forget it is a movie. And in many ways, it feels that Winter's Bone is to Jennifer Lawrence what The Believer was to Ryan Gosling, as her performance is nothing short of perfect.

Genre: Drama, Mystery

Actor: Ashlee Thompson, Casey MacLaren, Dale Dickey, Garret Dillahunt, Isaiah Stone, Jennifer Lawrence, John Hawkes, Kevin Breznahan, Lauren Sweetser, Ronnie Hall, Shelley Waggener, Sheryl Lee, Tate Taylor

Director: Debra Granik

Rating: R

Is courage still courage when you have no choices left? What do you do when you're pressed to the wall and have no way to go? Maria, a pretty, modest and hardworking girl living in a small Colombian town, where the only career choice (thus not being a choice, really) is working in a floral plant, packing and distributing flowers - a dead-end job with killer hours and zero-tolerance boss. Yet, it's money. Until the day Maria gets pregnant and her choices become even more limited. By accident, she makes acquaintance with a guy who turns out to be her way out - and the way is out to become a drug mule, transporting drugs in your stomach across the border to the American soil. A job dangerous in many aspects, illegal and potentially deadly, but also paid well. Maria decides to take the only way out, a way that may be a one-way street. Maria Full of Grace is a gut-wrenching story about survival in a seemingly hopeless situation. It's about taking that one chance that has all the potential to go south, and investing in it all the hope you have left, and all the survival instinct you have in your heart and soul. And when everything that could go bad does, and everything turns from bad to worse beyond imagination, it's about standing strong and not giving up, no matter what. Though technically not a documentary, it's real beyond belief, and you can be sure Colombia is full of Marias - just hoping for a decent life, ready to sacrifice the very life itself to obtain it. It's a masterpiece of its genre and it also boasts one of the best posters in the history of the cinema. Highly recommended.

Genre: Crime, Drama, Thriller

Actor: Catalina Sandino Moreno, Charles Albert Patiño, Guilied Lopez, Jhon Álex Toro, Johanna Andrea Mora, John Álex Toro, Orlando Tobón, Patricia Rae, Selenis Leyva, Victor Macias

Director: Joshua Marston

Rating: R

Contemplative English literature professor Vivian leaves New York for Reno, Nevada, to facilitate her divorce from a lifeless marriage. There she meets Cay, a sculptor and free spirit living relatively uncloseted for the time. What starts as an inspiring friendship soon turns to attraction. It is partly the story of Vivian's sexual awakening, partly a transformative love story persuasively depicted through earnest, unadorned dialogue and love scenes, and vulnerable performances. A heartfelt and tender romance, the scenes are delightfully set to a soundtrack of Patsy Cline and Johnny Cash singles and filmed over the expansive horizons of the Nevada desert.

Genre: Drama, Romance

Actor: Alex McArthur, Andra Akers, Antony Ponzini, Audra Lindley, Dean Butler, Denise Crosby, Donna Deitch, Gwen Welles, Helen Shaver, James Staley, Jeffrey Tambor, Katie La Bourdette, Patricia Charbonneau, Tyler Tyhurst

Director: Donna Deitch

A residential dispute spirals out of control into full, xenophobia-fueled tragedy in this straightforward and elegantly made film that comes from a now-bygone era of mid-budget dramas for adults. House of Sand and Fog may come off as excessively bleak to viewers today, but it manages to capture a very particular mood of paranoia and distrust common in post-9/11 American cinema. And if nothing else, the film is worth watching for a trio of powerful performances that never resort to overacting: from Iranian actress Shohreh Aghdashloo, English screen legend Ben Kingsley, and an always compelling Jennifer Connelly, who was arguably at the peak of her career in the early 2000s.

Genre: Drama

Actor: Ben Kingsley, Frances Fisher, Jennifer Connelly, Jonathan Ahdout, Kia Jam, Kim Dickens, Navi Rawat, Ron Eldard, Shohreh Aghdashloo

Director: Vadim Perelman