These 10 classic romantic movies are a cut above the rest. Classic romantic movies come in all shapes and sizes. Some movies put two characters into screwball situations while others keep the characters struggling to find true love. The best of the movies received Oscar nominations but all featured great performances by actors who matched up perfectly.

  1. “Annie Hall” – Woody Allen’s masterpiece casts himself as a neurotic New York Jewish man who tries to overcome his relationship problems in one of the best classic romantic movies. The movie is a quirky, unusual film where Allen, at times, stops and talks to the audience. The movie earned five Oscar nominations.

  2. “It Happened One Night” – Clark Gable stars in this screwball classic romantic movie, one of the earliest in the genre. Gable stars as newspaperman who falls for an uptight heiress, played by Claudette Colbert. The movie was the most successful comedy of the time, winning the top five Academy Awards for the year.

  3. “Roman Holiday”Audrey Hepburn and Gregory Peck star in this fairy tale, one of the best classic romantic movies. Peck stars as a newspaper reporter and Hepburn is a princess running away from her obligations. The movie earned ten Oscar nominations and Hepburn won for Best Actress.

  4. “The Philadelphia Story” – Based on a Broadway play, this remains one of the best classic romantic movies. Cary Grant, Katherine Hepburn and James Stewart star in the movie, a story of romance in the rich upper class world. The movie earned six Oscar nominations, winning James Stewart his only Best Actor award.

  5. “Adam’s Rib” – This battle of the sexes is one of the best classic romantic movies of all time. Katherine Hepburn and Spencer Tracy star in this movie about married attorneys who end up representing different partiers in a divorce case. The movie was the sixth of nine films starring Tracy and Hepburn.

  6. “City Lights”Charlie Chaplin stars in one of the earliest of the great classic romantic comedies, released in 1931. Chaplin plays The Tramp as he attempts to help a blind girl raise the money for surgery to regain her eyesigh knowing he may lose her when she sees him for the first time.

  7. “His Girl Friday” – Cary Grant stars in one of the greatest classic romantic movies ever made. Howard Hawks’ directed this film about a news editor who attempts to convince his ex-wife to return to work to chase a hot news story. The movie did not receive a single Oscar nomination but remains a true classic.

  8. “The Apartment” – It has been said that when interviewing new employees, Steven Spielberg will attempt to have a discussion of this classic romantic movie and if the interviewee knows nothing about the movie, he will not get the job. It is Billy Wilder’s masterpiece about an insurance man who loans his apartment out for extramarital affairs for company executives.

  9. “Some Like it Hot” – Jack Lemmon and Tony Curtis go in drag and tour with an all-women’s dance troupe after they witness a murder and find themselves running for their lives. They encounter Marilyn Monroe’s dancer and the romance blossoms. It received six Oscar nominations, winning one.

  10. “When Harry Met Sally”Billy Crystal and Meg Ryan star in this inventive classic romantic movie about two friends who find themselves falling in love. The movie is an interesting combination of great dialogue and interesting situations, making it one of the more recent additions to the list.