Top 20 Classic Romance Movies from the 1950s to 2000s — Ranked!

Romance movies have always held a special place in the hearts of moviegoers. Throughout the decades, from the 1950s to the early 2000s, several have stood out as iconic pieces of cinema. Here’s a rundown of some of the best romance films from each decade.

The 1950s saw the rise of romantic comedies and musicals, producing classics that continue to be loved. Audrey Hepburn starred as a European princess in Roman Holiday (1953), falling for an American reporter in a tale that remains timeless.

Judy Garland and James Mason brought to life an unforgettable story in A Star is Born (1954), which many consider the best adaptation of this oft-remade tale. Cary Grant and Deborah Kerr’s chemistry in An Affair to Remember (1957) captivated audiences as they portrayed two lovers with a promise to meet again. Singin’ in the Rain (1952) featured Gene Kelly falling for a chorus girl amidst the transition from silent films to “talkies.”

The 1960s welcomed the “New Hollywood” era, bringing fresh approaches to storytelling. Audrey Hepburn’s role in Breakfast at Tiffany’s (1961) remains iconic, as she navigates love while dealing with her complicated past.

Elizabeth Taylor and Richard Burton’s real-life romance began with their roles in Cleopatra (1963), which depicted the historical love affair between Cleopatra and Mark Antony. Dustin Hoffman’s performance in The Graduate (1967) introduced audiences to a young man entangled in a complicated love triangle with an older woman and her daughter.

The 1970s produced unforgettable films with unique romantic twists. Grease (1978) became a cultural phenomenon with its catchy tunes and the love story of Danny and Sandy. Robert Redford and Barbra Streisand starred in The Way We Were (1973), portraying two opposites who fall in love but struggle with their societal differences.

The 1980s brought a fresh flavor to romance films. John Cusack’s boom box moment in Say Anything (1989) is an iconic scene of romantic persistence. Can’t Buy Me Love (1987) featured a story about a high school nerd paying a popular girl to date him, only to realize the complexities of true popularity.

Tom Hanks and Daryl Hannah took audiences on a whimsical journey in Splash (1984), where Hanks’ character falls for a mermaid. Pretty in Pink (1986) told the story of Andie, a girl from a working-class background, navigating love in a world of social divisions.

The 1990s highlighted major stars like Meg Ryan and Julia Roberts. 10 Things I Hate About You (1999) became a beloved teen romantic comedy. A complex matchmaking scheme led to genuine love between Heath Ledger and Julia Stiles’ characters.

Pretty Woman (1990), with Richard Gere and Julia Roberts, told the tale of a wealthy man and a prostitute falling in love, challenging the norms of their respective lives. Sleepless in Seattle (1993) featured Tom Hanks and Meg Ryan in a modern adaptation of a classic tale.

Notting Hill (1999) brought together Hugh Grant and Julia Roberts in a story where a simple bookshop owner and a famous actress must deal with their significantly different lifestyles to be together.

The 2000s showcased romantic comedies with heartwarming clichés and meet-cutes. How To Lose a Guy in 10 Days (2003) had Kate Hudson and Matthew McConaughey unknowingly using each other for different romantic experiments but eventually developing real feelings.

Ryan Gosling and Rachel McAdams starred in The Notebook (2004), a tale of enduring love that survives despite social and war-time challenges. Katherine Heigl’s character in 27 Dresses (2008) embodied the eternal bridesmaid in a charming story about finding true love.

Source: Various sources