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

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by Orrin Konheim


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47 Comments

  1. Heat.

    Which of these is better than Pacino, Deniro, Kilmer, Hank Azaria, Ashley Judd, Dennis Hayspert, Tone loc, Henry Rollins, Jeremy Piven, John Voigt, Amy Brenneman, Natalie Portman, “that guy” king William Fichtner, and Machete himself Danny Trejo.

    Oh yeah and not to forget Buffalo Bill, Ted Levine; “It puts the lotion on the skin or else it gets the hose again”!!

  2. Couldn’t stop laughing when I read about Josh Lukas being the “era’s biggest romantic leading man”. LOL!!! I bet he’s been called a lot of things, but never the “era’s biggest romantic leading man”.

    I also believe The Life Aquatic with Steve Zissou deserves to be mentioned alongside The Royal Tennenbaums. Wes Anderson movies always have a great cast.

    • Orrin (article's author) on

      I thought Sweet Home Alabama cemented him as that, but I’d have to double check what the press were saying about him at the time.

      I love Wes Anderson films and Life Aquatic was a great film too. I kow a lot of other people didn’t like that one but I love sea adventures. I think it’s a higher order of casting when you have to assemble a group of actors for an extended adult family then a number of disparate shipmates.

      • If you find other movies with Lukas as the romantic lead, let me know. I think he’s a good actor, along the ranks of Matthew McConaughey. But unlike McConaughey, in my opinion, Lukas isn’t romantic lead material. He did shine though as the lead in both Stealth and Glory Road.

        Btw, I’m from the Philippines and I write movie reviews as a hobby and a sideline. I’d love to read more of your articles. Can you point me in the right direction? Thank you kind sir.

  3. ‘The Expendables’ anyone? I mean given they arent all brilliant actors, but seeing that many bad asses in one movie was almost too much to handle.

    • Orrin (article's author) on

      In Lucky Number Sliven, Morgan Freeman and Ben Kingsley had a pretty surprisably good chemistry. I don’t know if Bruce Willis really did too much except act tough and Bruce-Willis-like. It probably depends on how resonant the Willis-Hartnett scenes were for you. Also depends on how much you like Lucy Liu and Josh Hartnett. Hartnett himself is kind of a critical darling for choosing risky projects and turning down Superman, but only slightly

  4. Orrin (article's author) on

    I think the Ocean’s trilogy demonstrated the risks of putting a big ensemble together with big names just because they’re big names. The first one did work, but the 2nd was horrible and the plot was incomprehensible, because the star power was so enormous and the director didn’t keep their vanity in check. Nothing against the actors in the film, but I felt like it just led to an excess of vanity when you put Damon, Clooney, and Pitt together. Also, Casey Affleck never had enough to do

  5. Peter Boucher on

    There is an old saying that goes : “They Don’t Make Them Like They Used To”. I find it prevalent in 2 things, Classic Automobiles and Old Movies. Here is my example of a movie from the 60’s. “The Flight Of The Phoenix” (1965) . Cast : Jimmy Stewart, Sir Richard Attenborough, Peter Finch, Hardy Kruger, Dan Duryea, George Kennedy, Ernest Borgnine, Sir Ian Bannen, and directed by Robert Aldrich. Can’t go wrong there !!

    • Orrin (article's author) on

      Inception wasn’t a bad ensemble at all and an absolutely amazing movie. It might have been just a little bit better if they didn’t cast Michael Caine in the cliched old, wise man role he gets so often and if they replaced Ellen Page with someone just a little less cutesy. On the plus side, great use of Ken Wattanabe (sp?), Tom Hardy, Pete Postwenthaile (probably spelled that one too) and Leo and JGL made a good team. Yeah, I could see Inception being #21 or so, good pick

  6. Some people commenting here don’t get what 21st century means. The list only showcases movies from the 21st century, or the past 12 years.

    Having said that, there are a lot more films with brighter ensemble casts than the 10 mentioned above. I guess it all comes down to the author’s preference.

  7. What about “THE NUTTY PRESIDENT”? What a cast! Barack and Michelle, Eric Holder(also starred in “Fast and Furious”),Pelosi,Reid,Biden,Rachel Madcow and many more great comics.–Produced by Acorn Studios. Hilarious! And talk about an Ensemble-WOW!

  8. Peter Boucher on

    Well, Lets go back to the 1960’s and give you the casting list of a particular movie “It’s A Mad, Mad, Mad, Mad World” (1963). Here goes : Spencer Tracy, Sid Caesar, Milton Berle, Ethel Merman, Jonathan Winters, Jimmy Durante, Buddy Hackett, Mickey Rooney, Phil Silvers, Dick Shawn, Edie Adams, Dorothy Provine, Buster Keaton, The Three Stooges, Jim Backus, William Demarest, Peter Falk, Leo Gorcey, Carl Reiner, Zasu Pitts, Eddie Andersen, Jack Benny, Jerry Lewis, Norman Fell, Don Knotts. Director : Stanley Kramer.

  9. Coen Brothers movies deserve some mention:
    The Big Lebowski – Jeff Bridges, John Goodman, Steve Buscemi, Philip Seymour Hoffman, Julianne Moore, Peter Stormare and Tara Reid.
    Fargo- Frances McDormand, William H. Macy, Peter Stormare, John Carroll Lynch and Steve Buscemi

  10. “The Greatest Story Ever Told”-(1965)-Richard Conte,David McCallum,Roddy McDowall,John Wayne,Shelly Winters,Angela Landsbury,Man Von Sydow,Carrol Baker,Sal Mineo,Dorothy McGuire,Claude Rains,Pat Boone,Victor Buono,Jose Ferrer,Van Heflin,Sidney Poitier,Charlton Heston,Martin Landau,Donald Pleasence,Ed Wynn,Robert Blake,John Considine,Telly Savalas,Jamir Farr,Robert Loggia,Ed Wynn,…et al.

  11. What about Noises Off Christopher Reeve, Carol Burnett, Michael Caine, John Ritter, Nicolette Sheridan, Denholm Elliot, Mark Linn-Baker, Julie Hagerty, Marilu Henner. ?

  12. FYI, Saskatoon, Saskatchewan is not a “remote northern town” It’s a city and it not considered that far north or remote.

    • Peter Boucher on

      @ Twinwasp : Are you from Saskatoon, Saskatchewan ? If you do, do you know Neil Young as I know that he comes from that area. By the way, my Father’s side of the family all hail from the Quebec City area. I personally love Canada !!

  13. thestyxcrossing on

    Tia Dalma was the name of Naomie Harris’ CHARACTER in Pirates of the Caribbean. Also, No Bill Nighy?

  14. WHHHAAAAATTTTTT??????
    WHO MADE THIS LIST?
    ARE YOU MAD?

    Where’s Citizen Cane? Kramer vs Kramer? The Godfater 1 and 2? Titanic? Taxi Driver?

    In what planet is X-men better than Gladiator?
    In what parallel dimension is Juno better than Silence of the Lamb?

    Oh and if you say cast ensembles, how, when or where in the hell do any and I really do mean ANY of these movies have a better cast in any way, shaper or form than The Godfaher?.
    You talk about the Departed, Goodwill Hunting was much better. You talk about Dicaprio and Damon together I raise you a Denzel and Tom Hanks in Philadelphia. Or a Tom Cruise and a Dustin Hoffman in Rainman.

    I can give you a list of movies and believe me not one of these films will ever be amongst the best of all times. You need to either watch these movies or change careers.

  15. Al Pacino, James Caan, Robert Duvall, Robert De Niro, Diane Keaton, Talia Shire and the kudegra Marlo Brandon and Directed by Coppola.

    Have you ever hear of such a cast?

    This cast would run laps around any of the ones mentioned on this list. I would take the Godfather cast over any of these any day of the week and 1000 times over on Sunday.

  16. I’ll take both my comments back, I admit I did not read 21st century. As I am loud enough to protest the list, I am also man enough to admit I did not read the title as I should have.

  17. Peter Boucher on

    @ cotumarre………..21ST CENTURY WE ARE DISCUSSING HERE. WANNA SEE CAST FROM THE 20TH CENTURY ?? LOOK UP “ITS A MAD, MAD, MAD, MAD WORLD” (1963) THAT ONE CANNOT BE AND WILL NOT BE BEATEN.

  18. i’m shocked to see no mention of the Leathal Weapon series at all. they all worked so well with each other, well cast actors, introductions of new characters in each movie… not often every movie in a series is good, but Leathal Weapon is definately up there.

  19. Seeing as it just came out, I know it wouldn’t be on this list but hopefully the Avengers can stand next to the ones that are. I believe that the actors selected to portray their respective heroes (and villains) played their parts exceptionally well.

  20. Peter Boucher on

    This list falls into the category of the old saying “They don’t make them like they used too”. Just like Automobiles, movies will never come even close anymore to how important the story of the film is, instead the focus is now on Special Effects and having a Macho cast. If only the likes of Alfred Hitchcock, John Ford, Cecil B DeMille, etc. were alive today, we would have so many better movies.

  21. There is an obscure comedy named S.O.B. that is one of my favorites and has a great cast,
    Julie Andrews, William Holden, Marisa Berenson, Larry Hagman, Robert Loggia, Stuart Margolin, Richard Mulligan, Robert Preston, Craig Stevens, Loretta Swit, Robert Vaughn, Robert Webber, Shelly Winters, Rosanna Arquette, Benson Fong, Larry Storch, and Karen Austin.
    That is a pretty good cast for such an odd ball comedy which I own on VHS.

  22. What about black hawk down, Josh Hartnett, Eric Bana, Ewen McGregor, Orlando Bloom, Tom Hardy, To Sizemore, Ioan Gruffuld, Jeremy Piven, Ty Burrell

  23. “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

  24. “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!

  25. 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

  26. 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.

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