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