If you are like me, you are probably missing the good old romantic comedies we used to have. All we ever seem to get are gross out comedies or sleazy rated R comedies these days. I was thinking back and I think I enjoyed the romantic comedies of the 1990’s the best! Granted that was when I was dating the most and is also when I fell in love and got married, so it’s a very distinctive period of wonderful courtship and romance in my life. It seemed to be a perfect time for rom-coms.

Now, with that said, my list would probably be different than your list! Right off the start, you’ll probably be wondering why Pretty Woman didn’t make my list at all and wondering why some films did, but that’s the wonderful things about lists…they are versatile. (Just to answer that question in your head, I just didn’t like Pretty Woman, that’s all, it was a fine film, just not one of my favorite’s for top 15, that’s all.) Now, this list is supposed to get your mind thinking about your favorites and maybe discovering a few new films you probably just never got around to watching.  If that’s the case, then I’ve done my job effectively.

15. Clueless (1995)

A modern adaptation of Jane Austen’s Emma. I’m going to tell you a secret only my family knows…I’m a huge Jane Austen fan…OK, I admit it. I’m a sucker for the movies that have been adapted from her courtship novels and I love it when one gets the modern treatment. Directed by Amy Heckerling and starring Alicia Silverstone and Paul Rudd, it’s a fun little movie. This movie had a cleverly written screenplay that included a wide array of completely made up lingo. One of the promotional items distributed to tie-in with the film was a booklet called How to Speak Cluelessly; in it was a lexicon of many of the invented terms used for the Clueless world (some of which became part of real teen lingo at the time). An example: a Baldwin is a very handsome male, as in the famous sibling actors.

14.  Defending Your Life (1991)

This is an incredibly creative film about the after-life. Written and Directed by Albert Brooks and starring Albert and Meryl Streep, it’s a great examination of a person’s life and it carries with it the idea that life and especially LOVE carries over with us. It struck me very hard when I first watched in and I instantly fell in love with Albert and Meryl’s characters.

13.  I Love Trouble (1994)

I’m a huge fan of the films of Nancy Myers and Charles Shyer, and will run out to see one of their films the day they come out. This one was a box office bomb for some strange reason, and I just love it. It reminds me of the old Spencer Tracy and Katherine Hepburn movies with Nick Nolte in the Tracy role and Julia Roberts in the Hepburn role. Truth-be-told, they both do a good job in this movie, but Roberts definitely steals the show.  She’s mesmerizing in this. Roberts and Nolte reportedly did not get along throughout filming, although I don’t think you can tell with the final result. Roberts later described Nolte as “disgusting” whereas Nolte said she was “not a nice person.” Roberts disliked Nolte’s macho act, and was not shy or polite about letting him know. He, in turn, began deliberately engaging in it to piss her off. Regardless, neither one of them ever worked together again.

12.  Doc Hollywood (1991)

I wonder how many movie posters show Michael J. Fox pulling his sunglasses down…that’s like his signature move. This film was directed by Michael Canton-Jones and stars Michael J. Fox and Julie Warner.  I thought this movie was awesome, but it comes with a caveat…although it’s rate PG-13, it does have full-frontal nudity by Julie Warner when she walks out of the lake. It seems out of place for a light romantic comedy, to be honest. In this movie, Fox stars as a Doctor who gets into a car accident on his way through town and is forced into staying and working as the town Doctor.

11.  Housesitter (1992)

Great movie directed by none-other than Miss Piggy’s alter-ego, Frank Oz and stars Steve Martin and Goldie Hawn. I love these two actors and when you get them both together…magic. They loved working together so much they found another project years later by remaking the Neil Simon hit, The Out-of-Towners (1999). In this one she plays a con-artist that takes over his home.

10. Don’t Tell Her it’s Me (aka The Boyfriend School) (1990)

This is one of those films that appear on lists, that blow people’s minds. It had a very small theatrical release originally and then my brother and I found it on HBO late at night when we were in college and completely loved it.  We called it the best straight-to-HBO movie we ever saw, for years…before HBO started to produce their own stuff of course. It’s definitely a HIDDEN GEM, if you’ve never had the chance to see it. Directed by Malcolm Mowbray and stars Steve Guttenberg and Jami Gertz, it was originally released under the great song featured in the opening credits, but then changed later on video to the original source novel title. Guttenberg plays a guy who just survives cancer, only to find that he has let himself go and needs help making him more desirable to women. He recruits his romance author sister, Shelley Long, to help him get the girl of his dreams. Perfect setup for a rom-com.

9. The Cutting Edge (1992)

This film doesn’t hold up as well over time, just simply due to the fact that neither actor does their own skating and there is a cheesy and fake ice skating trick they use to win the whole competition, BUT– with that said, the chemistry between Moira Kelly and D. B. Sweeney is awesome and so much fun to watch.  The true joy in this movie is seeing these two actors go head to head. That’s why it makes my list. Directed by Paul Michael Glaser, who played Starsky in the original Starsky and Hutch!

8. Runaway Bride (1999)

Ok, yes, I like this film waaaaay more than Pretty Woman…I just do, okay? Same cast and crew, different characters and storyline. Directed by Garry Marshall and starring Julia Roberts and Richard Gere. Also, this is the second time Julia Roberts has a movie on this list (but not the last). Let’s be honest, we’re talking the 90’s…where Julia Roberts was queen of the rom-coms…but they were so good. This one is about a woman who runs away from several weddings, and then tries to avoid a reporter who comes to town to do a story about her.

7.  You’ve Got Mail (1998)

This movie is a remake of the fantastic Jimmy Stewart movie, The Shop Around The Corner, but written and directed by the incredible Nora Ephron. It stars Tom Hanks and Meg Ryan, who own competing bookstores, in the same block. Ryan’s store is named The Shop Around the Corner, the two main characters are latter day (mail) and present day (email) “pen pals”; they both know they are falling in love with their respective pen pals; when the man realizes who the woman really is, he pursues her, but is not sure the love match will work; in the end, they find they belong together. It’s cute.

6.  While You Were Sleeping (1995)

This is the first movie that put Sandra Bullock in a romantic comedy, and for years there was a race to see who would become the queen of the romantic comedies between Meg Ryan, Julia Roberts and Sandra…in the end I think it’s a tie between Sandra and Julia. Directed by Jon Turteltaub and starring Sandra Bullock and Bill Pullman, the film is about a woman who pretends to be the fiancee of a man in a coma. It’s a charming movie and I just realized that it’s set around Christmastime. It’s alarming how many movies on this list are set around Christmas, it’s a romantic time of year, I guess.

5.  Sleepless in Seattle (1993)

Another Nora Ephron movie and it also is with Tom Hanks and Meg Ryan. The 2nd of 3 movies that Meg Ryan and Nora Ephron did together the 3rd one being When Harry Met Sally, which was directed by Rob Reiner.  Rob Reiner plays Tom Hanks best friend in this movie. All around great people to be making movies with.  Sleepless in Seattle is about a recently widowed man whose son goes on a radio talk show to try and find his dad a new wife. The premise that the two lead characters meet at the Empire State Building comes from the Cary Grant Deborah Kerr movie An Affair To Remember. That film made another list of the top 15 for me, The Top 15 Cary Grant Movies. 

4. Speechless (1994)

This was another bomb when it came out to the theatres, but is such a good movie. Directed by Ron Underwood and starring Gena Davis and Michael Keaton, and is about two opposing speech writer’s during an election. The main reason to like this movie is because Keaton truly rocks in it.  He’s extremely funny and charming in this movie.  I think it’s my favorite of all of his movies…and that’s saying a lot because he’s done a lot of fun movies. It also has Christopher Reeve in it and he’s always great to watch as well…it’s strange to think that around this time they were both still portraying Superman and Batman respectively and if they were to do a Justice League together it would have made for a highly entertaining movie. Gena Davis is tall and good enough to have played Wonder Woman back then, what do you think?

3.  The American President (1995)

I keep wanting to yell out, “I Love That Movie, ” as I write this blog. I have to keep telling myself, you know that, afterall you are reading my top 15 list. This one is directed by Rob Reiner and stars Michael Douglas and Annette Benning, and is about a US President and a lobbyist dating while he is in the White House. This one is written by the amazing Aaron Sorkin. I rewatch this movie quite a bit and it’s a little sad every time I do, as Michael Douglas doesn’t actually act or impersonate any President that’s ever been in office and yet he personifies the perfect President that we have all always wanted in real life.

2.  Tin Cup (1996)

Is this a sports movie or a romantic comedy? Why, it’s a bit of both! It’s about a failed golf pro that hires a psychiatrist to help him qualify for the US Open. It’s directed by Ron Shelton and stars Kevin Costner and Rene Russo.  Kevin Costner is very good in this and was always a pretty good athlete in his own right.  A lot of the shots in the movie of his character playing golf is really Costner, playing golf. The scene at the end of the movie where Roy hits the shot into the water hazard again and again was based on an actual event. Gary McCord, the commentator with the handlebar mustache in the movie, is an actual commentator and pro golfer. In a 1987 tournament he had a shot similar to Kevin Costner’s. He needed a birdie to win and went for it. He hit the water over and over again and finally made the shot, but it cost him 15 strokes. In the movie Costner gets it in 12. The scene where Roy wins a bar bet by hitting a golf ball at a pelican also was based on a real life incident from McCord’s career.

1.  Notting Hill (1999)

My favorite romantic comedy of the 90’s.  Directed by Roger Michell and stars Julia Roberts (again) and Hugh Grant. It’s about a quiet travel book story owner who meets and falls in love with the most famous film star in the world.  Roberts and Grant are wonderful together. Hugh Grant got to play in a movie opposite Sandra Bullock a few years later, so Win/Win for him. Now all he has to do is find a way to get in there with Meg Ryan to get the trifecta…