10 Best Romantic Comedies to Watch over Valentine’s Day Weekend

With Valentine’s Day weekend upon us it’s a perfect time to share my personal Top 10 favorite Romantic Comedies. I’m a big film buff and my tastes include movies from the 1930’s till now. I do love my Bourne, Avengers and Gladiator movies, but being married, I have cultivated a fondness for funny (first priority) and touching (yes, I am getting a little soft as I get older) movies that are more to my wife’s liking.

Time and again the characters are arrogant, morally lacking, immature and maybe even pretty offensive, but their failures and weaknesses often remind me a little bit (if not a lot) about myself. And I love a film like Shaun of the Dead (in my top ten – and yes it’s a romantic comedy), where the slacker redeems himself in the end.

The Awful Truth 01

Here’s my list, starting with number 10:

10 – The More the Merrier – Not Rated (1943) – I have a soft spot for Jean Arthur. She was both a terrific dramatic and comedic actress and she shines in this romantic comedy opposite Joel McCrea.

9 – Date Night – Rated PG – (2010) – Steve Carell and Tina Fey are in top form as a married couple out on their weekly “date night.” I’m kinda glad my date nights with my wife have never been quite like this.

8 – Bringing up Baby – Not Rated (1938) – Katharine Hepburn and Cary Grant at their best in a sometimes silly but always funny “screwball comedy.”

7 – Hitch – Rated PG13 (2005) – Perfectly cast characters with Will Smith as a professional dating consultant and Kevin James as his client. Several truly “laugh out loud” moments in this film.

6 – The Awful Truth – Not Rated (1937) – Cary Grant and Irene Dunne in what is considered by many critics as the first, great “screwball comedy.” The late 1930’s was truly a grand period for film.

5 – Shaun of the Dead – Rated R mostly for language and some gore (2004) – The tagline says it all – “A Romantic Comedy with Zombies.” I do love a movie where the slacker redeems himself in the end.

4 – You’ve Got Mail – Rated PG (1998) – Two likeable actors playing two likeable characters, though Tom Hanks’ character Joe Fox starts off a bit arrogant. And I still love the setting stated by the title that captures the beginning of our dependence on the email age. Can’t believe that was only 1998.

3 – His Girl Friday – Not Rated (1940) – Again, starring Cary Grant, this time with Rosalind Russell. In this great romantic comedy they share some of the best movie dialogue ever and deliver every line with delicious precision.

2 – Groundhog Day – Rated PG (1993) – Bill Murray and Andie MacDowell in one of the funniest movies ever. I watch it almost every year near Groundhog Day. If you didn’t watch it then, it’s still a perfect Valentine’s Day movie.

When Harry Met Sally 01

And # 1 – When Harry Met Sally – Rated R for subject matter (1989) – This is my all time favorite comedy mostly because of it’s insights into relationships between men and women. It centers on Crystal’s character and his belief that “men and women can’t [just] be friends because the sex part always gets in the way.” In addition, you get two great comic couple relationships for the price of one. Billy Crystal and Meg Ryan as the title characters and Carrie Fisher and Bruno Kirby as their best friends. And for me (personally), I love the line, “You’re the worst kind; you’re high maintenance but you think you’re low maintenance,” (note to my bride – I Love You!)

And here are a few Honorable Mentions that didn’t quite get into my top ten (because there are only 10 spaces in a top 10 list), but these are all great:

Annie Hall (1977)
It Happened One Night (1934)
Moonstruck (1987)
Notting Hill (1999)
The Philadelphia Story (1940)
The Shop Around the Corner (1940)
While You Were Sleeping (1995)

Have a Happy (and fun) Valentine’s Day weekend!


About VocareMentor

Walk with the wise and become wise - Prov. 13:20 A lot of my blog comes out of the way I grew up. My parents divorced when I was 6 years old and I didn’t see much of my father. I had no understanding of how the lack of his presence in my life affected every choice I made as I grew up. Much of my adult life has been attempting to sort things out and catch up. Thus, what you’ll find on my blog are musings, thoughts, wisdom and ideas from history and pop culture. Themes: mentors, father/son, male/female, self-discovery, courage, stepping up, friendship and more.
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11 Responses to 10 Best Romantic Comedies to Watch over Valentine’s Day Weekend

  1. The Awful Truth is my favorite movie.

  2. Interesting list. Some I have not seen yet. Will have to check them out. Thanks. Thought I might find Sleepless in Seattle or An Affair to Remember of your list. Its Sheila and my anniversary tomorrow and will be taking her to Secret Garden french restaurant for our own romantic comedy.

  3. VocareMentor says:

    Reblogged this on VocareMentor.com and commented:

    If you can use some inspiration for your Valentine’s Day weekend movie viewing, I thought I might share my post from two years ago.

  4. “His Girl Friday” is probably the one I would say tops the list. There is also a strange (if that’s the word I’m looking for) undercurrent of bending gender roles, esp for a film from 1940. That the woman even has a job like a reporter in the first place is out there, and Grant is the one who is gets all “hysterical”.

    “Annie Hall” is one for only those secure in their relationship given the ending of the film. There is the fundamental theme of we need love; but as the movie points out sometimes it isn’t the one we would think it is.

    • VocareMentor says:

      When I was younger I was a big Annie Hall fan. The I discovered all the great films from the 30’s and 40’s. There are still so many I need to catch.

      • Likewise. I’d be interested in your take on some of the ones you discover. While I was making coffee this morning, I just clicked on TMC and it had Jimmy Stewart in “A Farewell to Arms” — something that would be only made by some indie film maker — and the acting and staging was so different, yet we need to learn to see the style in which it was made and not through our 21st century media eyes.

  5. jan says:

    One of my favorites is Love Actually. Tender Mercies is an unusual but ultimately romantic movie as well.

  6. mitchteemley says:

    Ah, When Harry Met Sally at #1. A man after my own heart.

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