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The 100 Best Romantic Comedies of All Time (Part Two)

Sabrina starring Humphrey Bogart and Audrey Hepburn. Photo: Paramount Pictures
Sabrina starring Humphrey Bogart and Audrey Hepburn. Photo: Paramount Pictures


While perhaps unrealistic and at times quite formulaic, the Hollywood recipe for the romantic comedy always tastes good when cooked to a simmering perfection. Some may be a delicious dessert, while others make for quite the fancy feast. Whatever the case may be, it’s high time we stop feeling ashamed for enjoying a good old-fashioned romantic comedy.

So, for this week’s List, I wanted to once again return to celebrating romantic comedies when they’re at their entertaining, romantic best. A couple months ago, I shared the first 50 of the best romantic comedies of all time. This month, I include the next 50 – again presented in no particular order. For the list, I’ve picked quite a variety of films from the classic to the new, from the traditional to the innovative.

And of course, if you’ve missed the first half of the list don’t forget to read it first HERE!

Without further ado, here are…


#51 Sabrina 

Year: 1954

Director: Billy Wilder

Starring: Humphrey Bogart, Audrey Hepburn and William Holden

My Take: The classic love triangle between Linus, Sabrina and David is very entertaining to watch and is still one of my favorites. I can never decide which one I love more. This one or the remake.

#52 13 Going on 30


Year: 2004

Director: Gary Winick

Starring: Jennifer Garner and Mark Ruffalo

My Take: Thirteen-year-old Jenna plays a game on her birthday and wakes up as a 30 year-old woman. What then unfolds is a love story about best friends in an adorable and really romantic film. The story takes some unexpected twists but has the perfect ending! The best part? The “Thriller” dance.

#53 Holiday 

Year: 1938

Director: George Cukor

Starring: Cary Grant and Katharine Hepburn

My Take: A Grant and Hepburn classic, the films tells the story of Johnny who falls in love with a very rich woman. But is she the right one for him?

#54 Clueless

Year: 1995

Director: Amy Heckerling

Starring: Alicia Silverstone and Paul Rudd

My Take: A modern retelling of Jane Austen’s Emma, this charming film is filled with humor, pop culture and lots of romance. It’s a ’90s classic for sure.

#55 The Lady Eve

Year: 1941

Director: Preston Sturges

Starring: Henry Fonda and Barbara Stanwyck

My Take: Card sharps target the heir (and snake expert) Charles on a ship, that is until Jean – one of the card sharps – falls in love with him. Unfortunately, when he learns the “truth” he angrily dumps her. To get her revenge, she returns by masquerading as an English lady to torture him. It’s a very romantic film with a lot of humor thrown into the mix.

#56 Sixteen Candles

Year: 1984

Director: John Hughes

Starring: Molly Ringwald and Michael Schoeffling

My Take: A John Hughes classic, this romantic comedy tells the story of Samantha, who has everything bad happen to her on her sixteenth birthday. But her tables turn when her crush, the most popular boy in school, Jake Ryan, discovers her feelings. While there are a few questionable moments in the film, the romance between Jake and Samantha still make teen girl’s hearts soar everywhere and it always makes for a fun re-watch. Especially the ending…

#57 Jerry Maguire


Year: 1996

Director: Cameron Crowe

Starring: Tom Cruise and Renee Zellweger

My Take: It’s hard to top the “you complete me” speech given from Jerry to Dorothy, the only woman who believes in him.

#58 Strictly Ballroom

Year: 1992

Director: Baz Luhrmann

Starring: Paul Mercurio and Tara Morice

My Take: Dirty Dancing meets Moulin Rouge, this quirky romantic dance comedy from Baz Luhrmann is one of my personal favorites.

#59 Sweet Home Alabama

Year: 2002

Director: Andy Tennant

Starring: Reese Witherspoon and Josh Lucas

My Take: This traditional romantic comedy about a southern woman trying to escape her past is pure fun! Who knew lightning could be so romantic…

#60 Emma

Year: 1996

Director: Douglas McGrath

Starring: Gwyneth Paltrow and Jeremy Northam

My Take: A young Gwyneth Paltrow shines in this film adaptation of Jane Austen’s classic novel romantic comedy style. Jeremy Northam made the perfect Mr. Knightley with the perfect blend of wit and old-fashioned charm.

By on May 20th, 2015

About Amber Topping

Amber works as a writer and digital publisher full-time and fell in love with stories and imagination at an early age. She has a Humanities and Film Degree from BYU, co-created The Silver Petticoat Review, contributed as a writer to various magazines, and has an MS in Publishing from Pace University, where she received the Publishing Award of Excellence and wrote her thesis on transmedia, Jane Austen, and the romance genre. Her ultimate dreams are publishing books, writing and producing movies, traveling around the world, and forming a creative village of talented storytellers trying to change the world through art.

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1 thought on “The 100 Best Romantic Comedies of All Time (Part Two)”

  1. Lots of favorites here. 13 Going on 30 is charming; love Sweet Home Alabama; Warm Bodies is oddly eccentric, but in a very sweet way; Austenland, just yes; Miss Pettigrew, Legally Blonde and The Proposal (Sandra Bullock is great) are always fab choices. Oh, and I heart Knight and Day. Such a cute flick. It’s been eons since I watched Sabrina or the “Bachelor” Shirley Temple film. Perhaps it’s time to remedy that. 🙂


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