One of the last great silent films, Charlie Chaplin’s City Lights deserves every bit of praise it has received in its nearly 90 years. Chaplin will always be considered one of the very best silent stars, but this film cements his much-deserved status as a romantic lead, as well.
Claudette Colbert and Clark Gable’s pairing in It Happened One Night paved the way for future romantic comedies about two people at odds with one another who can’t help but fall in love. It’s still funny, even after all these years, and the romance is still just as impactful.
A hugely influential film from the back half of the 20th century, Billy Wilder’s The Apartment stars Jack Lemmon and Shirley MacLaine in what many consider to be one of the greatest comedies (and certainly one of the greatest romantic comedies, at that). The two have an undeniable energy that latches onto the viewer and never lets go.
It’s fun to imagine what it must have been like to see The Philadelphia Story for the first time back in the 40s. Hollywood superstars Katharine Hepburn, Jimmy Stewart, and Cary Grant all star as the film’s three leads, making for one stacked romantic comedy that proves hard to beat still to this day.
Nora Ephron and Rob Reiner’s seminal late-80s classic has yet to be topped. Every aspect of the film is romantic comedy perfection, nailing both aspects of the genre without ever letting neither romance nor comedy take precedent over the other.