Home Articles 5 Romantic Comedy Movies To Watch At Any Given Time
5 Romantic Comedy Movies To Watch At Any Given Time

5 Romantic Comedy Movies To Watch At Any Given Time


I’ve always been a sucker for a good Rom-Com, from a young age I was hooked. To be fair, Romantic Comedies are easily put into production because its such an easy audience. People want to laugh and watch a relationship bloom, fall apart and then come back together because it’s a wistful wishful reality. What I want to do for you, my readers, is countdown a few of my favorites and why they make the genre better. I’m sure you are thinking but why now? What made you want to write this article at this time… well if I’m honest, we’ve had a recent cinematic resurgence of them thanks to Netflix and the booming success of an ALL ASIAN LED ROMCOM – Crazy Rich Asians. Which I’m sure means we may in 8 months become over saturated in rom-coms but I AM FOR IT READERS.

Anyways —

Never Been Kissed (1999)

Director: Raja Gosnell

Starring: Drew Barrymoore, Michael Vartan, David Arquette

Josie Grossy— need I say more. Oh, I do need to say more. Okay, if you have never watched this movie you are sorely missing out. It has an amazing cast ranging from Drew Barrymore, David Arquette, Molly Shannon, John C. Reilly and Michael Vartan. If you must know I went through a huge Michael Vartan phase as a teen because of a show called Alias starring Jennifer Garner and Michael Vartan.. I’m pretty sure it’s still on Netflix and is amazing. That is however besides the point. The reason I love this movie, is because it’s about a woman who returns to high school to write an expose type piece on the life of high school students and what makes being in high school so great. Interestingly Drew Barrymore returns as a student and meets a very handsome teacher (Michael Vartan) and yes they flirt— sort of. To be fair I don’t want to give away this whole movie because it’s gold. But it seriously is one of the best romantic comedies you will ever see, from a marijuana induced reggae dance scene to horribly mean teenage pranks at prom it is a film I will always go back to for laughs and to warm my heart.


While You Were Sleeping (1995)

Director: John Turteltaub

Starring: Sandra Bullock and Bill Pullman

Okay, this is one of two films centered around a holiday. To be fair I don’t see this as a “Christmas” movie but I definitely watch it around Christmas and I watched it like once a week as a child because I have/had a freak obsession with Sandra Bullock (who makes more than one appearance on this list.) Essentially this movie is about a woman who works at the transit authority station in Chicago, she has seen a man come through her gates every day for years and has fallen in love with him from behind the glass of her ticket booth. One day the man is mugged on the train platform and is pushed onto the tracks and knocked unconscious she jumps to action rolling him to safety in the knick of time. What ensues after is a raucous family reunion mixed with flat out lies and misunderstandings. I’m sure that sounds wildly interesting to you right? Well to sweeten the pot here are some of your other favorite 90’s actors in the mix to entice you to watch this movie : Peter Gallagher, Bill Pullman, Peter Boyle, Jack Warden and Glynis Johns.  Like I stated before I had a very weird obsession with Sandra Bullock as a kid, I think it was because she was in so many films as I was growing up that I just had a deep affinity for her because she was always there. She’s also sweet, gorgeous and funny to boot.


10 Things I Hate About You (1999)

Director: Gil Junger

Starring: Heath Ledger, Julia Styles, Joseph Gordon-Levitt, Larisa Oleynik

So the Lit-Major in me cannot leave out this Taming of the Shrew adaptation at all. Why? because Heath Ledger that’s why. Oh you need more than that, a young Joseph Gordon Levitt— there is that better? Well great now that we are on the same page. Yes, 10 Things I Hate About You is an adaptation of a Shakespearean play titled Taming of the Shrew and to be fair the concept of both the play and the film are very, very good. There is a perfectly lovely daughter and a perfectly un-lovely daughter. Neither of them ugly both of them intelligent one is just NICE and the other is not. I think I saw a lot of myself in this movie which is why I loved it so much. I’m the youngest of 4 girls, I have always compared myself to my sisters whether if that was looks, grades, eloquence, boys etc. I’ve always had someone who does it better than I. But this movie— let me just tell you reader. It is GOLD. There is the out of control house party, the jock ass-hat who thinks he can get whatever he wants with money, the sweet sensitive guy and the mystery man. Everything you could want and more. Also it is set in this larger than life high school scenario where prom is impending and our main character Katarina has little to no interest in attending, such a nice and refreshing point of view of a teenage girl, well at least at the time.


The Proposal (2009)

Director : Anne Fletcher

Starring: Sandra Bullock, Ryan Reynolds, Betty White

I couldn’t leave this movie off this list, it is ridiculously adorable and sweet. To me this was one of the best romantic comedies of the late 2000’s. The thing I think I cherish the most about this movie is the extremely likable characters. Although you want to dislike Sandra B’s Margaret Tate you kind of can’t (I think that is the curse of Sandra Bullock as much as you want to dislike her its very difficult to do so…) Meanwhile, there is also adorable Malin Akerman who plays Gertrude who again you want to dislike but how the hell can you when she’s a kindergarten teacher and she’s Ryan Reynolds high school sweetheart. Oh wait.. I’m talking as if you’ve seen this. If you haven’t seen this because you were under a rock Ryan Reynold’s Andrew, is Margarets assistant and she is the boss from hell but she is also in the career Andrew wants most as an editor at a major publisher. Margaret is about to get deported back to Canada for letting her VISA expire and plots to just marry Andrew to get around the deportation. Please don’t sleep on this movie if you already have once, here’s an extra fun thing — what do Betty White, Lil’ Jon and Native American traditions have in common… answer: this movie.


Love Actually (2003)

Director: Richard Curtis

Starring: Hugh Grant, Liam Neeson, Emma Thompson, Colin Firth, & Bill Nighy

Did you really think I was going to make this list and NOT include Love Actually, it is ridiculously adorable, it’s holiday oriented, it’s multiple intertwining stories that are multiple aspects of the “love” relationship that at the time was extremely unique. Since this movie came out many have tried to re-create it’s interlaced, multi-character storyline but none in my opinion have been as successful. My favorite story-line from this film is probably Hugh Grant and Martine McCutcheon who play the Prime Minister and the new secretary, respectively. I love their storyline because it’s really sweet how they are kind of around the edge of each other the whole film until finally coming to the realization of their feelings. If you are a true romantic at heart who bypassed this film for whatever crap reason you gave yourself… RETHINK that and then watch it.

That is my list. I wish I could make it 30x longer because I’ve left out so many. So here are some honorable mentions:

  • Notting Hill
  • Four Weddings and a Funeral
  • Pretty Woman
  • You’ve Got Mail
  • She’s All That
  • My Best Friends Wedding
  • The Wedding Singer
  • Drive Me Crazy
  • One Fine Day
  • Fools Rush In
  • Blast from the Past

So once you’ve finished “To All the Boy’s I’ve Ever Loved” for the 80th time and you’ve maxed out your credit card on watching “Crazy Rich Asians” throw it back to some old school RomComs, grab a glass of wine, some bunch-a-crunch and jalapeño popcorn and tuck in to the classics that made the genre.

Natasha Paiva Natasha Paiva is a San Diego native born and raised along the shores of Ocean Beach and hills of Point Loma. Natasha is a graduate of San Diego State University with a degree in English Literature, California currently she writes in her free time while working full time for a tech company. She hopes to one day see one of her scripts produced into a film, or one of her books published.