5 Favorites Redux #46: Favorite Romantic Comedies

Welcome to 5 Favorites. Each week, I will put together a list of my 5 favorites (films, performances, whatever strikes my fancy) along with commentary on a given topic each week, usually in relation to a specific film releasing that week.

The Broken Hearts Gallery is this coming weekend’s only wide release. The romantic comedy stars Geraldine Viswanathan (Blockers) and Dacre Montgomery (Power Rangers (2017)) and is from first-time director/screenwriter Natalie Krinsky about an art gallery assistant (Viswanathan) who has collected souvenirs from every relationship she’s ever been in while a new flame yields promise for a longterm relationship.

The underlying story is inventive, but the film isn’t likely to take off at the box office. With the relative newness of its stars, there aren’t a lot of choices for a 5 Favorites article. So, I’m going a bit broader looking at my favorite romantic comedies.

It Happened One Night (1934)

Becoming the first film in history to score Oscars for all five top categories (Picture, Director, Actor, Actress, and Writing Adaptation), It Happened One Night was a success all around with stars Clark Gable and Claudette Colbert turning in indelible performances and Frank Capra doing what he does best as director.

Colbert plays a spoiled heiress who runs away from home and ends up sharing numerous modes of transportation with Gable’s reporter in search of a story. While they begin as antagonistic rivals, the film witnesses their slowly growing appreciation for one another that eventually builds into romance. A hilarious, heartfelt, and superb film, It Happened One Night deserves its well-earned reputation.

The Philadelphia Story (1941)

A recently divorced wealthy socialite (Katharine Hepburn) is at the center of a love quadrangle between three men: her ex-husband (Cary Grant) who helps out a fellow tabloid reporter (James Stewart) at Hepburn’s wedding to her current betrothed (John Howard). This screwball comedy unwinds over almost two hours as one incident after the other threatens to upend convention and romance.

George Cukor’s wry direction keeps everything on target as Hepburn, Stewart, and Grant apply their considerable talents to the unwinding story. Who does she end up with? You’ll have to watch the film to find out, but you’ll enjoy the ride getting to the end.

Annie Hall (1977)

While Woody Allen started his writing career on television in the 1950s, his directorial debut came with 1966’s What’s Up, Tiger Lily?. Over the next decade, Allen developed a reputation as one of the freshest new voices in cinema with 1977’s Best Picture winner, Annie Hall, launching his career into the stratosphere.

Starring Diane Keaton as the titular ditz, the film follows the burgeoning relationship between Annie Hall and comedian Alvy Singer. The hilarious film impressively defined Allen’s signature self-deprecating style and helped refine and bolster Keaton’s career. Both would produce some terrific work over the decades, Allen with numerous ensemble features and Keaton with a stellar array of endearing performances. This film is an impressive and entertaining effort.

Four Weddings and a Funeral (1994)

Although British comedies had been finding modest success in the United States, Four Weddings and a Funeral helped cement that subgenre’s legacy with a surprise Best Picture nomination along with an Original Screenplay nod for screenwriter Richard Curtis.

The film also made stars out of Hugh Grant and Kristin Scott Thomas and gave Andie McDowell a new direction in her career. Grant plays a committed bachelor who, over the course of the five titular occasions, slowly falls in love with McDowell while his friends find, nurture, and lose love around them. A hilarious and touching film, there were few films that came out of the new British Comedy Invasion that could have rivaled it and, to date, none of them have.

Love, Simon (2018)

Prolific television showrunner Greg Berlanti shifted to the big screen to bring this adaptation of Becky Albertalli’s novel to cinemas nationwide. Starring an endearingly awkward Nick Robinson, the film follows Simon’s attempt to handle his sudden and unexpected push out of the closet while trying to uncover the identity of a mysterious correspondent who found him through the online presence that outed him.

As the teenager tries to come to terms with his new identity, newfound celebrity, and correspondence crush, we learn a great deal about life and love in a modern romantic environment. Countless films have explored High School in similar ways, but this one brought that conversation to the queer community in a resounding and engaging way. Humorous and sweetly intoxicating, Love, Simon is a wonder.

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