6 Movies Like Chicago (2002)

Staff & contributors

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

From a 1926 play to the iconic 1975 stage musical to Rob Marshall's 2002 extravaganza, Chicag0 has had a strong hold on popular culture. In a way, it's existed almost as long as cinema itself and its transformation across mediums and modes of expression has been well documented. The film carries all the marks of its theatrical predecessors, the expansive sets, the luscious costumes, the sleek characters whose banter and songs alike testify to their great chemistry — there's a lot to admire in such a self-referential spectacle. A black-comedy-fuelled musical about corruption and deceit set during the Jazz Age, Chicago fulfils all its promises. With a stellar ensemble cast featuring Renée Zellweger, Catherine Zeta-Jones, Richard Gere, and John C. Reily, in tandem with dazzling camerawork and most exquisite chiaroscuro lighting, this one brings the stage to the movies. I mean it in the best possible way!

Gosford Park inspired screenwriter Julian Fellowes to create Downton Abbey — but don’t let that association fool you, because this is no quaint, sentimental period drama but a scalding satire of 1930s England class relations (even though Maggie Smith does play a withering dowager countess here, too). Robert Altman, master orchestrator of ensembles, assembled a banquet of performers here, including Michael Gambon, Kristin Scott Thomas, and Charles Dance as the well-to-do attendees of a hunting party on a grand estate. Working furiously to meet their every whim is the house’s domestic staff, played by such talents as Emily Watson, Helen Mirren, Kelly Macdonald, and Clive Owen.

The murder comes over an hour into the film, which ought to tell you about its real focus (Altman actually called Gosford Park a “who cares whodunnit”). In place of Agatha Christie-style intrigue is brilliant characterization and storytelling. Even at 137 minutes, 30-plus characters mean time is of the essence, but Altman and his actors miraculously find a way to convey a deep sense of each person — especially those downstairs. This tangle of rich lives never gets overwhelming, though, because Gosford Park is expertly paced. It’s nothing less than a joy to sit back and experience the masterful unraveling of its many threads, each more revelatory than the last.

Genre: Drama, Mystery, Thriller

Actor: Adrian Scarborough, Alan Bates, Bob Balaban, Camilla Rutherford, Charles Dance, Claudie Blakley, Clive Owen, Derek Jacobi, Eileen Atkins, Emily Watson, Emma Buckley, Finty Williams, Frances Low, Frank Thornton, Geraldine Somerville, Gregor Henderson-Begg, Helen Mirren, James Wilby, Jeremy Northam, Jeremy Swift, Joanna Maude, John Atterbury, Kelly Macdonald, Kristin Scott Thomas, Laura Harling, Laurence Fox, Leo Bill, Lucy Cohu, Maggie Smith, Meg Wynn Owen, Michael Gambon, Natalie Danks-Smith, Natasha Wightman, Richard E. Grant, Ron Webster, Ryan Phillippe, Sarah Flind, Sophie Thompson, Stephen Fry, Teresa Churcher, Tom Hollander, Trent Ford

Director: Robert Altman

Rating: R

Kimberly Peirce's first–out of only three—film was a smashing success, mostly due to her dedication to the subject matter. Peirce spent years researching the life and tragic death of Brandon Teena after reading an article about him in The Village Voice. She felt a particular kind of kinship as a queer person herself, and wanted to construct a story out of real facts that would put the spotlight on love and the desire for connection, and not that much on the violence which dominated the public discourse. In Falls City, Nebraska, the director conducted interviews with Lana Tisdale (Brandon's girlfriend) and her mother, while attending the ongoing trial. She took years to cast the lead and from hundreds of cis women, lesbians, and trans people, she chose the unknown actress Hilary Swank, who went on to win the Best Actress Academy Award (and the irony of that is not lost on us). The film features fantastic performances aplenty and very raw storytelling, visualized by neorealist style and low lighting. Direct references were the films of Martin Scorcese and John Cassavetes, but Boys Don't Cry has its own blend of beauty and cruelty to take pride in.

Genre: Crime, Drama

Actor: Alicia Goranson, Alison Folland, Brendan Sexton III, Caitlin Wehrle, Cheyenne Rushing, Chloe Sevigny, Craig Erickson, Gabriel Horn, Gail Cronauer, Guilford Adams, Hilary Swank, Jackson D. Kane, Jeannetta Arnette, Jerry Haynes, Josh Ridgway, Libby Villari, Lisa Renee Wilson, Lou Perryman, Matt McGrath, Paige Carl Griggs, Peter Sarsgaard, Rob Campbell, Robert Prentiss, Shana McClendon

Director: Kimberly Peirce

Rating: R

Don’t be fooled by its obvious parallels to Ghost (not a bad film, but a very different one): Truly, Madly, Deeply isn’t much concerned with the supernatural logistics of its back-from-the-dead-boyfriend premise, and it doesn’t feature any psychics or murders, either. In fact, there’s an argument to be made that everything that takes place here happens in its protagonist's imagination — that’s how much it ignores the ‘how’ of it all.

Instead, this deeply warm rom-com from the great Anthony Minghella grapples head-on with the emotional challenges of grief and moving on. Juliet Stevenson’s performance as the bereft Nina is up there as one of the most moving portrayals of loss the screen has seen, and not just because of how believable her intense cry-acting is. When she realizes her deceased boyfriend Jamie (Alan Rickman, as seductive and sardonic as always) has returned to the land of the living, her euphoria brings to aching life the dream that everyone who’s ever lost a loved one must surely have dreamt: how joyous it would be to see them again. Blending such raw observations with wry humor — and anchored by two leads with genuine chemistry — this is a profoundly moving and rewarding movie.

Genre: Comedy, Drama, Fantasy, Romance, TV Movie

Actor: Alan Rickman, Arturo Venegas, Bill Paterson, Christopher Rozycki, David Ryall, Deborah Findlay, Eddie Vincent, Frank Baker, Heather Williams, Jenny Howe, Juliet Stevenson, Keith Bartlett, Mark Long, Michael Maloney, Nitin Ganatra, Richard Syms, Stella Maris, Teddy Kempner, Terry Molloy, Tony Bluto, Vania Vilers

Director: Anthony Minghella

C.R.A.Z.Y. is crazy good, so to speak. A portrait of a French-Canadian family in 70's Quebec that will knock your socks right off, it's the story of a boy struggling with his identity and his relationship with his father. Featuring a killer soundtrack (including but not limited to Bowie, Pink Floyd, Rolling Stones), it received Best Canadian Film in 2005 at Toronto International Film Festival. There are many things I would like to say about C.R.A.Z.Y. but I fear it's one of those films you enjoy best when you go into them not knowing much.

Genre: Comedy, Drama

Actor: Alex Gravel, Anik Vermette, Claude Gagnon, Danielle Proulx, Denis Trudel, Élizabeth Adam, Francis Ducharme, Hélène Grégoire, Isabelle Pagé, Jean-Alexandre Létourneau, Jean-Louis Roux, Jean-Marc Vallée, Joël LeMay, Marc-André Grondin, Marie-Michelle Duchesne, Marie-Yong Godbout-Turgeon, Mariloup Wolfe, Maxime Le Flaguais, Maxime Tremblay, Michel Côté, Michel Laperrière, Mohamed Majd, Natasha Thompson, Pierre-Luc Brillant

Director: Jean-Marc Vallée

Rating: Not Rated

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. 

Genre: Comedy, Drama, Romance

Actor: Alex Kalognomos, Alysia Reiner, Cesar Ramos, Jessica Hecht, Joe Marinelli, Lee Brooks, M.C. Gainey, Marylouise Burke, Mikael Sharafyan, Missy Doty, Patrick Gallagher, Paul Giamatti, Peter Dennis, Phil Reeves, Robert Covarrubias, Sandra Oh, Shake Tukhmanyan, Shaun Duke, Stephanie Faracy, Thomas Haden Church, Toni Howard, Virginia Madsen

Director: Alexander Payne

Rating: R

In the sea of mommy-horror films, Run Rabbit Run would float somewhere in the middle. Despite Sarah Snook's imposing commitment to playing a mother haunted by her past, the story doesn't meet her halfway with a memorable script. The dynamic between mother and daughter gets stuck in an exhausting loop of sudden bursts of anger and angst followed by glaringly quick reconciliation. Twists and scares are present as Snook's character, also named Sarah, confronts the dark and disturbing truths of her past, but it feels more mandatory than useful. The potential for transforming gripping familial tension into horror is lost in a meandering mother/daughter fight.

Genre: Drama, Horror, Thriller

Actor: Damon Herriman, Genevieve Morris, Greta Scacchi, Julia Davis, Katherine Slattery, Lily LaTorre, Michala Banas, Naomi Rukavina, Neil Melville, Sarah Snook, Trevor Jamieson

Director: Daina Reid