Top 10 Greatest Movie Casting Ensembles of the 21st Century

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Determining the ten best film ensembles of the 21st Century was a much harder list to narrow down than I originally anticipated. There are a lot of movies that succeed on the basis of having a lot of big-name stars attached to them. To create a list like this, I tried to focus on movies where care was taken by casting to find the right pieces and fit them together so they’d equal the sum of their parts. To decide between apples and oranges, I also decided to favor larger ensembles figuring it was more difficult to fill in a larger number of roles. This eliminated worthy movies based around quartets from consideration (Doubt, Sideways…) although they show up in my honorable mention section.

10. The Help/Almost Famous

Too often female-centered films exist solely to rack up actress nominations, which is why I have to give credit to these two films for featuring so many great female roles. In addition to featuring strong performances by the highly dependable Philip Seymour Hoffman and Jason Lee, Almost Famous features Frances McDormand and Kate Hudson as two polar opposite influences on young protagonist Patrick Fugit: one’s a stern and worrisome mother and the other’s a free-wheeling groupie that the mother’s so worried about. Add Zooey Deschannel (before she was synonymous with the term “adorkable”) as rebellious sister and you’ve got three strong and impeccably-cast female parts.

Similarly, The Help brings together a sense of diverse personalities to show the good (Jessica Chastain), the bad (Bryce Dallas Howard, very against-type), and the in-between (newcomer Ahna O’Reilly) of women’s culture in the South. Journeywoman Viola Davis, who was awarded an Oscar nomination for just eight minutes of screentime in Doubt, shines very brightly in the co-lead role. The film also has juicy parts for three elderly stateswomen of cinema: Mary Steenburgen, Allison Janney and Sissy Spacek.

Hidden gems: Scroll down the imdb page of Almost Famous and you’ll see all kinds of surprises: Jay Baruchel, Eric Stonestreet, Nick Swardson, Rainn Wilson, and Jimmy Fallon. For the Help, Sissy Spacek counts. A lot of people didn’t recognize her right off the bat.

9. Little Miss Sunshine

Alan Arkin felt so ashamed to be singled out of the cast for a best supporting actor that when asked to speculate on why he won, he replied, “I think it’s because of my age. Everyone thinks I’m going to keel over in a year or two, [so they decided to] give me a little bonus.” The dark comedy hits very emotional highs because of the chemistry between the six leads who play a downtrodden family driving through the Pacific Southwest en route to a beauty paegent. Paul Dano and Abigail Breslin showed us they were among the most talented stars in their respective age brackets; Greg Kinnear and Toni Collette reminded us how underrated they are; Steve Carrell showed us he can branch out past comedy, and Alan Arkin got an Oscar, whether he liked it or not (monstersandcritics.com).

Hidden gems: Breaking Bad’s Bryan Cranston and 24’s Mary Lynn Ruskjab have bit parts.

8. A Beautiful Mind

The film might be one of the less memorable Best Picture winners at the Oscars, but that’s not to take away from the quality of the cast. How often does the era’s biggest romantic leading man (Josh Lukas starred alongside Reese Whitherspoon in Sweet Home Alabama the following year) appear in a film as the 6th billed lead? Russell Crowe gives one of my favorite performances as mathematician John Nash and Jennifer Connelly lives up to her potential as his long-frustrated wife. Paul Bettany’s performance as a roommate who’s not all he seems to be is underrecognized. Elder statesmen Christopher Plummer and Judd Hirsch enhance the cast while a quartet of younger actors– Adam Goldberg, Jason Gray-Stanford (Monk), Anthony Rapp (Rent), and Josh Lukas- play his colleagues from his Princeton days. The film’s casting directors Janet Hirhsenson and Jane Jenkins explain in the book “A Star is Found” that for the quartet, they took care to cast four diverse looking people that made an impression right away and were easily distinguishable.

7. Juno, 2007

With the exception of Allison Janey (on the basis of her wide filmography, not because she was bad here), no one in this cast had ever been used so well on screen or shined as brightly since. Watching Ellen Page take on Kitty Pryde as hip and relatable in X-Men: The Last Stand and you’ll see just how underutilized she would have been without a Diablo Cody script to rescue her. Michael Cera and Jason Bateman were given their best opportunities to expand on their shy boy and straight man screen personas respectively. Similarly, Jennifer Garner and J.K. Simmons also had especially meaty roles

6. Royal Tennenbaums, 2001

Gene Hackman fits in perfectly into the artsy melancholy of Wes Anderson’s world as the head of the overachieving Tennenbaum clan. Luke Wilson, Ben Stiller, and Gwyneth Paltrow play his three kids as wonderfully neurotic messes alongside Owen Wilson (the film’s co-writer) as the clan’s surrogate son and Anjelica Huston as the unforgiving wife. Paltrow, in particular, makes an impression. She was just three years removed from Shakespeare in Love at this point and her role as the near-catatonically depressed Margo was a complete 180 from the glamorous ladies she usually played. Also impressive are the contributions by Danny Glover and Bill Murray (a frequent Wes Anderson player), which isn’t lessened by the fact that their roles were surprisingly minor for actors of their stature.

Hidden gem: Kumar Pallana was originally the proprietor of the Cosmic Coffee shop where Wes Anderson frequented at the University of Texas. Pallana was one of many local friends he cast as extras in his first film before giving Pallana larger roles leading to an eventual career as a character actor. Here, he plays the notary public and friend of Gene Hackman.

5. X-Men

As opposed to comic book films that focus on either strong men or box office stars, X-Men put meticulous detail into its casting and set the tone for comic book films to be taken seriously as drama (paving the way for Chris Nolan’s Batman series which could easily be substituted here as an example of an impeccably casted ensemble). With the possible exceptions of Patrick Stewart and Ian McKellen (who fit their comic counterparts too well to be discarded), not a single casting choice was conventional. Hugh Jackman were essentially discovered and introduced to American audiences while former child star Anna Paquin (who won an Oscar at the age of 11) was given the fuel to reignite her career. Storm was made intelligent and sexy through the casting of Halle Berry while former Bond girl Famke Jannsen spiced up the chemistry with Jackman as Jean Grey.

Hidden gem: Taylor Mane, who played Sabretooth, wasn’t an actor at all but a pro-wrestler cast because of his enormous size. Coincidentally, Mane is from the remote Canadian town of Saskatoon, Saskatchewan- which could easily pass for the unnamed town along the Canadian frontier where Sabretooth hails from. (In the animated TV series, Sabretooth hails from Edmonton, Alberta.)

4. Up in the Air

When Descendants co-producer called George Clooney’s performance in that film a career best, he owed Jason Reitman an apology. Under Reitman’s direction, Clooney really gets deglamourized as a travelling businessmen who comes to realize a lifestyle obsessed with frequent flier miles is quite shallow. Character actors Melanie Lynskey (who often plays unassuming women) and Amy Morton contrast nicely against Clooney’s forceful charisma as sisters living less of a high life. Meanwhile, Vera Farminga provides a sexual chemistry (that later leads to danger and heartbreak) with Clooney that veers in the opposite direction in terms of excitement. Anna Kendrick, in a break-out role, also provides a perfect foil to Clooney and Farminga.

Hidden gems: All the people (except for Zach Galifanakas and J.K. Simmons) who were shown responding to being fired were not actors but real-life people who had been fired. Reitman put up an advertisement offering them the chance to tell their real-life story for the camera. Gosh, I hope he paid them.

3. Adaptation

Nicolas Cage does double duty as two of the four main characters in this loopy Charlie Kaufman film and brilliantly pulls off tender and emotional scenes with himself. If that isn’t enough to make a case for this film, it features Meryl Streep’s sexiest performance, as a writer for the New Yorker who throws caution to the wind and has an affair with one of her subjects. Her romantic partner is played by Chris Cooper who won an Oscar as wily horticulturalist John LaRoche. On top of that, the supporting cast includes Maggie Gyllenhaal, Ron Livingston (Office Space), and Judy Greer as a perky waitress.

Hidden gems: Tilda Swinton, several years before being recognizable for Chronicles of Narnia, and Michael Clayton plays Nicolas Cage’s literary agent.

2. Chicago

Transforming middle-aged thespian Richard Gere into a singing tap dancer and the cheery Rene Zellweger into a vampy attention-whore were not easy tasks but they resulted in pitch perfect casting for this Oscar-winning film. Zellweger’s Roxy Hart was paired off with Catherine Zeta-Jones which fit well with her darker disposition. The film also opened a lot of doors for John C. Rielly, who got a Best Supporting Actor nomination as pushover husband Amos Hart and had a strong cast in smaller roles with Lucy Liu, Christine Barinski and Queen Latifah. Consider that this cast was competing against the comparisons to Broadway counterparts and musicals weren’t en vogue in 2002 and it makes Chicago’s success all the more impressive.

Hidden gem: The part of the M.C. was Taye Diggs.

1. Departed

Over the last five years, Leonardo DiCaprio and Matt Damon have become the two most in-demand actors for ambitious film projects. In addition to being Marty Scorsese’s muse, DiCaprio has worked with the best directors in Hollywood including James Cameron, Clint Eastwood, Ed Zwick, Ridley Scott, and Christopher Nolan. Similarly, Matt Damon’s leveraging of the Bourne series to produce a wide array of riskier choices and his consistency in quality has made his filmography the envy of any 20-something actor today.

The Departed had both young stars teaming up together in an adversarial relationship that gave both stars a chance to shine in different scenes. The two were paired up with icon Jack Nicholson with a stellar supporting cast that included Mark Wahlberg (who got an Oscar nomination for stealing several scenes as a foul-mouthed police lieutenant), Martin Sheen and Alec Baldwin. Vera Farminga also turned a few heads as a psychiatrist who gets involved with both the leads.

Hidden gems: Comic Anthony Anderson plays Leo DiCaprio’s training school buddy.

Greatest Movie Ensembles Playlist

Check out our Movie Cast Ensembles Playlist on YouTube for more clips, including the honorable mentions listed below.

Another 10 for Honorable Mention (and narrowing these down were just as hard):

Aviator: Leonardo DiCaprio, John C. Reilly, Cate Blanchett, Kate Beckinsdale, Ian Holm, Alan Alda, Alec Baldwin, Adam Scott, Gwen Stefani, Danny Huston, Jude Law, Willem Dafoe

Batman Begins: Christian Bale, Michael Caine, Morgan Freeman, Cillian Murphy, Liam Neeson, Tom Wilkinson, Ken Watanabe, Katie Holmes

Doubt: Philip Seymour Hoffman, Meryl Streep, Amy Adams, Viola Davis

Hairspray: Nikki Blonsky, Jon Travolta, Christopher Walken, Allison Janney, Zac Efron, Elijah Kelly, Queen Latifah, James Marsden, Michelle Pfeiffer, Brittney Snow, Amanda Byrnes

The Hours: Meryl Streep, Nicole Kidman, Julianne Moore, Ed Harris, Toni Collette, John C. Reilly, Liam Neeson

Margin Call: Zach Quinto, Kevin Spacey, Jeremy Irons, Paul Bettany, Simon Baker, Demi Moore, Stanley Tucci

Pirates of the Caribbean: Dead Man’s Chest-Johnny Depp, Orlando Bloom, Kiera Knightley, Jonathan Pryce, Geoffery Rush, Jack Davenport, MacKenzie Crook, Kevin McNally, Tia Dalma, Tom Hollander, Stellan Skaarsgard

Ray: Jamie Foxx, Regina King, Kerry Washington, Sharon Warren, C.J. Saunders, Curtis Armstrong, Terrence Howard, Larenz Tate, Bookeem Woodbine, Richard Schiff

Sideways: Paul Giammatti, Thomas Haden Church, Virginia Madsen, Sandra Oh

Tropic Thunder: Ben Stiller, Jack Black, Robert Downey Jr., Jay Baruchel, Danny McBride, Tom Curuise, Matthew McConaughey, Nick Nolte

Just to cover all my bases, films I haven’t seen which reportedly have very strong ensembles: Gosford Park, Crash, Closer

by Orrin Konheim

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47 Comments

  1. “A Few Good Men” – Tom Cruise, Demi Moore, Jack Nicholson, Kevin Bacon, Kevin Pollack, Keifer Sutherland, Small scenes by Cuba Gooding, Jr. and Noah Wyle

  2. “A Time To Kill” – Matthew McConaughey, Samuel L. Jackson, Ashley Judd, Sandra Bullock, Kevin Spacey, Kiefer Sutherland, Donald Sutherland, Oliver Platt, Charles S. Dutton. BigTime!

  3. I know it falls short for three years, but how about the Thin Red Line’s cast? Wherever you look there is a famous actor. Sean Penn, Adrien Brody, Jim Caviezel, Ben Chaplin, Jared Leto, George Clooney, John Cusack, Woody Harrelson, Elias Koteas, Nick Nolte, John C. Reilly, John Travolta. Probably I’m still missing some names

  4. Painful to see the departe in number one, even with the big names it was one of the worst casting ever done, the lead was awful. looked like a kid with add and I find it hard to believe anyone bought he was a cop.