It would be hard to argue that Romantic Comedies aren’t some of cinema’s most accurate mirrors to society, the concepts, the stories and the superstar actors they use coming to define eras and put a timestamp on the relevancy of everyone involved. Over the years we’ve had classics like The Apartment, When Harry Met Sally and even more recently The Big Sick, which all celebrated timely ideals and used very contemporary stars, while Netflix seem to have taken the entire genre upon their own back in recent years to make teen heartthrobs like Noah Centineo a part of the zeitgeist and bring the dying rom-com genre firmly back into the public consciousness.
For this list, we’ve analysed the contemporary era of cinema (1970 and beyond) for the very best rom-com ensemble casts that came to define eras, surprise audiences and ultimately sell their film, whether the picture could be considered good or not.
As a rule, we’ve avoided films that are firmly attached to other genres, such as musicals like Grease and La La Land or dramas like The Silver Linings Playbook and Shakespeare In Love (all of which have rom-com elements), and have judged all casts based on casts alone – beware, there may be some seriously trash movies in the list ahead!
In no particular order…
1. No Strings Attached (2011)
Starring that year’s Best Actress Oscar winner Natalie Portman and arguably the decade’s most trustworthy go-to rom-com leading man Ashton Kutcher, this early 2010s offering from Ivan Reitman, the director of Ghostbusters (1984), featured a stacked cast of future industry leaders including Oscar-nominated director Greta Gerwig and multi-time Emmy nominee Mindy Kaling.
Oscar winning actor Kevin Kline played Kutcher’s father, meanwhile Lake Bell, Ophelia Lovibond, Ludacris and Spider-Man: Into the Spider-Verse’s Jake Johnson offered their two cents in some of the film’s smaller roles, filling No Strings Attached to the brim with some of the decade’s most influential and recognisable names.
Cast: Natalie Portman, Ashton Kutcher, Kevin Kline, Lake Bell, Cary Elwes, Greta Gerwig, Olivia Thirlby, Ludacris, Mindy Kaling, Jake Johnson, Ophelia Lovibond
2. You’ve Got Mail (1998)
The 2nd half of the Meg Ryan/Tom Hanks rom-com double bill, You’ve Got Mail, also directed by Nora Ephron (When Harry Met Sally), peaks its older sister to this slot due to each of its stars (particularly Hanks) being even closer to the top of their game, with the supporting cast being nothing short of a who’s who of top class late 90s names.
Leading male Tom Hanks had won two Oscars between Sleepless In Seattle and You’ve Got Mail (for Philadelphia and Forrest Gump) and was about to win his 3rd for 1998’s Saving Private Ryan, while the supporting cast featured that year’s Supporting Actor Oscar nominee Greg Kinnear, award-winning comedian Dave Chappelle, Steve Zahn, Parker Posey and even Chris Messina in a small role.
Cast: Meg Ryan, Tom Hanks, Greg Kinnear, Parker Posey, Dave Chappelle, Steve Zahn, Heather Burns, Jean Stapleton, Chris Messina
3. He’s Just Not That Into You (2009)
In the late 2000s, the trend of putting as many famous faces into a rom-com as possible became a thing, and much of that was thanks to the unheralded success of He’s Just Not That Into You (2009). This Ken Kwapis directed venture beats out its closely linked ensemble rom-com brethren Valentine’s Day (which starred just about everyone including Taylor Swift) to this spot on the list for that very reason.
Starring a leading cast of height-of-their-powers actresses Drew Barrymore and Jennifer Aniston, He’s Just Not That Into You also fanned the growing star power of Scarlett Johansson and Bradley Cooper to offer a film which had a little bit of everything for everyone. Even late rom-com phase Ben Affleck got a look in!
Cast: Drew Barrymore, Jennifer Aniston, Scarlett Johansson, Ginnifer Goodwin, Jennifer Connelly, Justin Long, Ben Affleck, Bradley Cooper, Kevin Connolly, Kris Kristofferson, Marc Silverstein, Busy Phillipps
4. Crazy Rich Asians (2018)
Combining a mix of up-and-coming talent with experienced and hugely respected professionals, John M. Chu’s Crazy Rich Asians was one of 2018’s most universally beloved surprise hits.
To make sure this particular rom-com grabbed the attention of casual cinema goers, the cast was stacked to the brim with recognisable and on-trend faces including Awkwafina (Ocean’s 8), Gemma Chan (Fantastic Beasts and Where To Find Them; Mary Queen of Scots) and Constance Wu, with Malaysian born Michelle Yeoh being perhaps the pick of the bunch as the talent for all ages, the Crouching Tiger Hidden Dragon and Sunshine actress upping the film’s classy ensemble tenfold to make it one of the most tantalising of the decade.
Cast: Awkwafina, Henry Golding, Gemma Chan, Constance Wu, Harry Shum Jr., Michelle Yeoh, Ken Jeong, Sonoya Mizuno
5. Crazy, Stupid, Love. (2011)
Speaking of crazy…
Crazy, Stupid, Love. put together such a cast of Oscar-nominees that the casting is almost Oscar-worthy within itself. Julianne Moore, who was by this point already a 4-time Oscar nominee, was joined by the multi-award winning Steve Carell on the cusp of his dramatic breakthrough, the now 2-time Oscar nominee Ryan Gosling, Oscar winner and 2-time nominee Emma Stone, Oscar winner Marisa Tomei, 3-time Golden Globe nominee Kevin Bacon and even award-winning musician Josh Groban.
If ever there was a cast to sell you on a film, this would be it.
Cast: Steve Carell, Ryan Gosling, Emma Stone, Julianne Moore, Marisa Tomei, Analeigh Tipton, Kevin Bacon, Josh Groban, Joey King, John Carroll Lynch