There have been some pretty amazing romantic comedies since 2001. There were a few movies that were in the conversation for this list, but did not make it, as I wanted to cut back on crossover between this list and our Top 10 Movies to Watch on Date Night.
Without further ado, here are my favorite “new-age” romantic comedies:
Will Smith tries to help Kevin James woo the woman of his dreams. The tricks he helps others use will not work for himself, though. The chemistry between the two leads is wonderful. Will Smith’s charisma matched with Kevin James’ lovable personality is what makes this movie so charming.
09. The Big Sick
Based on a true story in the life of writer/actor Kumail Nanjiani, The Big Sick is the perfect tale of what happens when the road gets the toughest for two soulmates. The humor is present, but the amount of heart in this script and on the screen is something to marvel.
08. Love, Actually
Commonly looked at as one of the quintessential romantic comedies of, well, all time, Love, Actually is quite the treat. Being told the stories of several characters, some intertwined, we are led through a beautiful web of love, laughing along the way.
07. The Holiday
It is funny to see a 21st Century movie that has already not aged well, as The Holiday tells the story of two women who exchange homes over the winter holiday (AirBnB before it was cool). Outside of this premise, the movie has aged as well as stars Kate Winslet and Cameron Diaz have. Supported by Jude Law and Jack Black, the cast is splendid and the story is entertaining.
06. Definitely, Maybe
The first crossover from our “Date Night” list, Definitely, Maybe has everything a romantic comedy needs…and more. This isn’t your typical romantic comedy, as throughout the film, Abigail Breslin is attempting to discover which one of her father’s past lovers is her mother. This movie is extremely witty and it is surprisingly fun to follow along in the daughter’s journey through her father’s stories.
05. Knocked Up
One of the top few “unintended pregnancy” movies, this also functions perfectly as a romantic comedy. Knocked Up is a sort of opposite to The Big Sick. These two people are not soulmates, they simply had a one night stand. Where the common thread lies, is the hurdle this couple must take to find their own true happiness.
The very best of the “unplanned pregnancy” movies, Juno is chocked full of sarcasm and wit. Ellen Page brilliantly shows how teenage pregnancy can affect a young woman. Michael Cera doesn’t overplay his father/boyfriend role, and seamlessly fits into the background. While the journey may not fully feel like a romantic comedy, Juno’s destination is love (and tic-tacs).
03. The 40 Year Old Virgin
This will always be Steve Carrell’s defining role, to me. Sure, Michael Scott is iconic, but the hilarity that ensues when a 40 year old virgin attempts to get laid is some of the funniest moments you will ever witness, romantic or not.
02. Forgetting Sarah Marshall
It amazes me how perfectly cast this ensemble is. From Jonah Hill’s fanboy hotel employee, to Mila Kunis’ carefree hostess, to Jason Segel’s silly, lovable jingle writer, to the odd, quirky couple played by Jack McBrayer and Maria Thayer, everyone here is on point. This has one of the funniest scripts that will ever be written.
01. 500 Days of Summer
The second, and final, crossover from our “Date Night” list, 500 Days of Summer is a near perfect film. Joseph Gordon-Levitt and Zooey Deschanel feel like they could be a couple in real life. This is a testament to their acting chops. The way JGL looks at Zooey feels real, the way she pushes back from his clingy-ness feels real. This movie makes me happy and brings a smile to my face, even only thinking about it.