Top 25 Romantic Comedy Movies of All-Time: Exploring Issues in Rom-Com Movies Volume XXVII

It dawned on while planning in my mind future rom-com posts in this series: Exploring Issues in Rom-Com Movies; that I needed a top 25 post list that I can update from time-to-time as my tastes change, new movies enter the mix, and movies rise and fall out of favor.

Going off two past posts, Warmth dated December 1, 2012: which had my top 10 list, and 11-20 Favorite Rom-coms of All-time dated April 14, 2013 I have re-thought the list. So now I submit my new and updated top 25 list, with a brief justification for its rank.

(Note: This list was updated: 7-24-2015, 3-13-2015, 1-9-2015, 7-10-2014, 3-30-2014, 9-1-2013)

E.C. Henry's Top 25 Romantic Comedies of All-Time:

1. "While You Were Sleeping" Justification: This is the movie that really kicked it all off for me.  I paid to watch this movie in the theatres 5 times, which is a record for me.  This movie has a lot of heart and warmth.  I also love the comedy brought in by a buffoon, wrong guy/Bellamy, "Joe Fusco Jr." as played by Michael Rispoli.  Note: this movie moved up in my rankings following a very favorable re-watch of the movie, where I found myself smiling the whole way through this, eventhough I knew EXACTLY what was going to happen next.  
2. "13 Going on 30" Justification: Inner story of a girl flash-forwarding in her life to see the ramifications if her wish came true and she dismissed her childhood sweetheart.  The way this story chose to handle this wish-fulfillment theme really resonated with me.  It's like the popular girls at school reconsidering their choices post high school...  Deep stuff.  Goes WAYYY beyond a mere coming-of-age, cautionary tale.  And the acting by Judy Greer as "Lucy Wyman" Jennifer Garner as "Jenna Rink", Mark Ruffalo as "Matt Flemhaff", Sean Marquette as "Young Matt" and Andy Serkis as "Richard" are all top notch.
3. "Dan in Real Life" Justification: Huge fan of Steve Carrell.  Thought his romance with Juliette Binochette worked.  Liked the dance-off scene in the bar.  Was VERY impressed by the work done by the actresses who play Dan's daughters.  This movie has some real warmth too it, AND it's based on the East Coast which has a big attraction for me.
4. "How to Loose a Guy in 10 Days" Justification: Love how the screenwriters dealt with the dueling agendas of Andie Anderson and Benjamin Barry which leads to a lot of comedy in a bevy of different settings.  This was a very well thought out movie.  Best acting by a romantic pair in this history of rom-com movies by Matthew McConanhuey and Kate Hudson.  And the supporting actors and actresses are very well thought out and add nicely to the main story. 
5. "Splash" Justification: Nice balance of romance and humor.  Darryl Hannah is gorgeous; the most beautiful heroine in romantic comedy of all-time.  John Candy is funny, as is Eugine Levy in his attempt at exposing Madison's secret.  (Note: I re-watched this movie on cable January 8,2015 and was pleasantly reminded how good of an actor Tom Hanks; one of the best jobs as a lead in rom-com of all-time!)
6. "Sleepless In Seattle" Justification: Meg Ryan.  HUGE fan of her.  I loved watching her work her magic in its full glory in this movie.   The theme plays off destiny and how that works in romance is pretty high concept and makes you think.  And the ending where Tom Hanks and Meg Ryan are holding hands, looking at each other and smiling is priceless.  Just genius stuff on display there, both the filmmakers sensitivityNOT to have too much talking when you come to the realization that you've just met your romantic soulmate for life, and the fine job both actors to pull that moment off.  
7. "The 40-Year-Old Virgin" Justification: This is one of the funniest movies ever made, and the late blooming romance between Andy and Trish is just enough.  Andy's friends from work played by Paul Rudd, Romany Malco, and Seth Rogen all work.  Steve Carell is perfectly cast as the lead, and Elizabeth Banks and Leslie Mann both do great jobs in scenes as the wrong girl/female Bellamy.
8. "As Good as It Gets" Justification: Jack Nicholson's portrayal of Melvin Udall grows on you over time.  If someone like Mevin Udall can fall in love, their is hope for us all. 
9. "My Big Fat Greek Wedding" Justification: Interesting take on a high concept theme: can a great love survive a chaotic family?  Great acting by Michael Constantine as "Gus Portacolos", and Nia Vadalos is a solid protagonist for the audience to follow. 
10. "Crazy, Stupid, Love" Justification: I like it when rom-com's try to have more than one relationship in them, and this one has three: Steve Carrell's strained marriage, then his foray with other women.  Steve Carrell's son's infactuation with an older girl at school.  And Ryan Gosling trading in his playboy ways for a more serious relationship with Steve Carrell's oldest daughter played by Emma Stone. 
11. "Ted" Justification: The Ted character is very funny.  The farce of having a teddy bear, who helps the boy who wished him to life, now scoring pot so the two of them can get high yields a lot of laughs.  
12.  "(500) Days of Summer" Justification: Most realistic depiction of the true heartache involved with falling in love with the wrong person that I can ever remember watching.   Great acting by both Joesph Gordon Levitt as "Tom" and Zoey Deschanell as "Summer Finn".  I really liked Tom's dance number to the Hall and Oats song, "You Make My Dreams Come True", and the ending to this movie where Tom meets a new love interest at a job interview was really good.
13. "Enchanted" Justification: Amy Adams steals the show as a come-to-life ex-cartoon princess who finds her great love in the real world.
14. "A Fish Called Wanda" Justification: John Cleese, and a nice blend of sophisticated, British hummor. 
15. "Silver Linings Playbook" Justification: Jennifer Lawrence's great acting, and over time Bradley Cooper's character becomes more and more bareable.  The plot of this story has bit of a mystery eliment to it too, as the attemped romatic manipulated set-up isn't clear untill the end.  And this movie has a very strong ending after a slow start.
16. "Romancing the Stone" Justification: Nice blend of action, occassional comedy and romance.  And Kathleen Turner is totally hot!
17. "The Proposal" Justification: Great acting turned in by Ryan Reynolds and Sandra Bullock.  
18. "Green Card" Justification: Late blooming charm between Gerald Dipardeu and Andie MacDowel.
19. "Definately, Maybe" Justification: A well plotted romance over a man and the three love interests in his life: Ilsa Fisher, Elizabeth Banks, and Rachel Weitz.
20. "Love Actually" Justification: I really liked the romance between Hugh Grant and the Martine McCutcheon, especially where they're caught kissing at the kid's play.
21. "Alex and Emma" Justification: Huge fan of Luke Wilson.  A very likable performance turned in by Kate Hudson.
22. "What Women Want" Justification: Solid acting by Mel Gibson and Hellen Hunt.
23. "Happy Gilmore" Justification: Best Adam Sandler movie.   Got me to laugh a lot.
24. "Hitch"  Justification: I wasn't real sold on the main love storyline between Hitch and Sara (Will Smith/Eva Mendez) but the Albert and Allegra (Kevin Smith/Amber Valletta) B romantic storyline made me smile a lot.  
25. "Adventureland" Justification: I'm a sucker for coming of age movies.  Really identified with the Jessie Eisner's character.  And for him to end up with a hottie like Kristen Steward, buddy I'm all in!!  Where the fuck was Kristen Stewart when I was 16 years old?  O shit, I don't even think she was born yet.  Gotta quit dating myself.  

Other Worthwile Rom-coms That Just Missed the Cut:

1. "Weekend at Bernies" Justification: A guilty pleasure.  Lots of black humor that you need to be in right mood for before you watch this.  Love the farce of putting up a front that your boss is still alive to improve your chances and not not upset the apple cart as you pursue a love interest.
2. "50 First Dates" Justification: This movie comes on late.  Drew Barrymore at her cutest.
3. "Stranger than Fiction" Justification:I kinda liked the Maggie Gylenhal/Will Farrell romance. 
4. "The Spectacluar Now" Justification: This coming of age at the end of your high school experience has much the same appeal as "Adventureland."  But this show has a theme that I could really relate to: a boy who was faced with drifing through life, or chosing a deepen a mature, steadyminded girl who was on the right track in life and could help him.  No laughs in this movie, but it is an OUTSTANDING teen drama.
5. "Trainwreck" Justification: A very solid story.  Amy Schumer's dramatic acting was a pleasant suprise.  Lots of different forms of comedy in this one, but this raunch-com wasn't near as funny as Apatow's other classic film, "The 40-Year-Old Virgin", and some off the raunch was rather excessive and was a turn-off to me.  Still, a worthwhile film to watch, study and enjoy.

So there it is, my top 25 romantic comedies of all-time.  I plan on revisiting this list from time to time and updating it.  And when I do I'll add a note citing its revision.