Top 10 Greatest Rom-Com Ensemble Casts

Stacked from top to bottom with A-list talent “My Big Fat Greek Wedding” was not. That’s why it came as a major surprise when it went on to become the 9th highest-grossing film of 2002, taking home a whopping $368 million! However, as anyone who’s seen the film can attest, a big reason for its success was its ensemble cast of newcomers, bit players, character actors, and one NSYNC member. With a lack of recognizable faces, Toula’s family feels real, with each character fleshed out and totally believable – despite their screwball antics. The film is proof that you don’t need a stable of Hollywood juggernauts to make a great rom-com, you just need well-written characters the audience can identify with.

Written and directed by the incomparable Nancy Meyers, “The Holiday” is the story of two women living in London and Los Angeles, respectively, who decide to swap homes - and lives - over the Christmas holidays. Played by Cameron Diaz and Kate Winslet, Amanda and Iris throw themselves headfirst into their new environments and soon find themselves falling for Graham and Miles, played by Jude Law and Jack Black. Rounding out the rest of the cast is legendary actor Eli Wallach of “The Good, the Bad and the Ugly” fame, Rufus Sewell, Edward Burns, Shannyn Sossamon, and even a young John Krasinski! And let’s not forget cameos by Dustin Hoffman, James Franco, and Lindsay Lohan! Who wasn’t in this movie?

Oftentimes the recipe for creating a great ensemble cast is as simple as having the film take place in high school. Case in point: “10 Things I Hate About You.” Starring Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt, all of whom would go on to have excellent careers in film, “10 Things I Hate About You” puts a modern-day spin on the classic Shakespeare comedy, “The Taming of the Shrew.” The high school setting begets an ensemble, with parents, teachers, guidance counselors, and students needed throughout. As such, we get well-rounded and hilarious performances from Larisa Oleynik, Larry Miller, David Krumholtz, and future Oscar winner Allison Janney. You’ll laugh, you’ll cry, and you’ll say, “Hey, isn’t that…”

Richard Curtis has been behind some of the most beloved and successful romantic comedies of all time. He wrote “Four Weddings and a Funeral” and earned an Academy Award nomination for Best Original Screenplay as a result. Part of what makes Curtis a great writer is his ability to turn even the smallest character into a memorable one. The cast of “Four Weddings and a Funeral” benefits from this in a big way, as everyone from Hugh Grant and Andie MacDowell to John Hannah and Kristin Scott Thomas – and even Rowan Atkinson – are able to steal a scene throughout the course of the film. Curtis’s writing brings the ensemble to life… something he would do again in 2003… but more on that later!

Scarlett Johansson, Ben Affleck, Jennifer Aniston, Bradley Cooper, Drew Barrymore, Jennifer Connelly, Ginnifer Goodwin, and Justin Long… need we say more? No matter how you cut it, “He’s Just Not That into You” is overflowing with A-list talent. Unfortunately, this ultimately proved detrimental, as many critics felt the film was overstuffed. Despite the mixed critical reception, it still became an audience favorite and pulled in $178 million at the box office. It’s a film that proves star power matters, drawing in audiences while also elevating the shortcomings of the script.

Describing “Clueless” for their list of the Top 25 Best Romantic Comedies of All Time, Vanity Fair quipped, “There would be no Regina George without Cher.” Cher was the definitive 90s high schooler for many, with more nuanced than the “Mean Girls” character she paved the way for and armed with Valley Girl jargon and fashion inspo for days. With a genre-defining character like Cher, it can be easy to forget that “Clueless” boasts one of the best rom-com ensembles of all time. Like, for real. From her on-screen besties Stacey Dash and the late Brittany Murphy to a pre-“Scrubs” Donald Faison and a pre-everything Paul Rudd, “Clueless” was stacked! Also, shoutout to a post-“Princess Bride” Wallace Shawn. This cast was truly inconceivable!

It didn’t take long for the accolades to start pouring in once this film was released in 2018. The sixth highest-grossing romantic comedy of all time, “Crazy Rich Asians” was widely praised for its Asian ensemble cast, which included up and comers and screen legends alike. Constance Wu, Henry Golding, Awkwafina, and Gemma Chan infused the film with youth and comedy, while film icons Michelle Yeoh, Lisa Lu, and Ken Jeong brought a sense of gravitas that their younger co-stars were lacking. And yet, this is just the tip of the ensemble iceberg. Everyone in the film is great, and each character no matter how small brings something unique to the table.

Based on the final product, we have a feeling that the casting director for “Crazy, Stupid, Love” got everyone they wanted and then some! With 13 Academy Award nominations and three wins between them, Steve Carell, Ryan Gosling, Emma Stone, Julianne Moore, Marisa Tomei, and Kevin Bacon brought professionalism and a wealth of experience to this 2011 rom-com – and it shows on screen. The comedic chemistry between Carell and Gosling is outstanding, while the romantic chemistry between Gosling and Stone is so strong they would find themselves playing lovers again in 2013’s “Gangster Squad” and again in 2016’s “La La Land.” Rounding out the cast is esteemed character actor John Carroll Lynch and Grammy nominee Josh Groban. Crazy indeed!

It isn’t hard to put butts in seats when you have a cast like this! “Working Girl” managed to nab multiple 80s icons for its main cast, with Melanie Griffith, Harrison Ford, and Sigourney Weaver leading the way. The Academy Award-nominated film, which sees Griffith’s character hatching a scheme to reclaim an idea stolen by her boss, also featured future A-list stars Alec Baldwin and Kevin Spacey (though the latter is hard-pressed to find work these days), as well as talented character actors Joan Cusack and Oliver Platt. Unsurprisingly, the film was a critical and commercial success, and helped turn Griffith into a full-fledged superstar.

Before we unveil our top pick, here are some honorable mentions:

“Trainwreck” (2015)
Name a Judd Apatow Film That Doesn’t Have a Stacked Cast

“Forgetting Sarah Marshall” (2008)
Jason Segel, Mila Kunis, Kristen Bell, Russell Brand, Jonah Hill... Shall We Keep Going?

“Notting Hill” (1999)
If It’s Written by Richard Curtis, It’s Got a Great Cast

“Much Ado About Nothing” (1993)
This Ensemble Cast Has a Combined 4 Academy Awards & Over 20 Nominations!

“Knocked Up” (2007)
There Isn’t Enough Screen Time to Properly Highlight All the Incredible Comedians

No matter what you think of this Richard Curtis film, you cannot deny that it has one of the best ensemble casts of all time - of any genre! Included in the ten interweaving storylines about love lost and gained in London in the lead up to Christmas are Keira Knightley, Alan Rickman, Liam Neeson, Colin Firth, Hugh Grant, Chiwetel Ejiofor, Bill Nighy, Laura Linney, Rowan Atkinson, Emma Thompson, a pre-“Hobbit” Martin Freeman, and a pre-“Walking Dead” Andrew Lincoln. And that’s without mentioning A-list cameos by Billy Bob Thornton, Claudia Schiffer, and January Jones. We literally almost ran out of time reading off those names. So yeah, when it comes to the top rom-com ensemble cast of all time, “Love Actually” takes the cake.