Posted April 19, 2012 by Mike Dean in Movies

Rom-Com Nostalgia: Top Ten Romantic Comedies of the ’90s

Romantic Comedies of the 1990’s held some of the biggest laughs, most heartfelt characters, and brow raising story twists that would make the genre one of the biggest in Hollywood over the following decade.  Here’s a top ten of some of the 90’s best.

10. While You Were Sleeping 

The charming and cute Sandra Bullock plays the role of that girl in the background nobody notices.  Trying to manage an impulsive white lie that spins out of control, an unexpected romance with her fake fiancée’s brother comes front and center.  Bill Pullman’s everyday man persona plays perfectly off Bullock’s good-hearted nature and quirky sense of humor.

9.  Kissing a Fool

David Schwimmer shows some range in this one.  Shedding his sheepish, nerdy guy from Friends, he plays a cocky local sportscaster that needs absolute proof his fiancée is the right girl.  Jason Lee rounds out the cast and gives this story not just the answer to a hypothetical that’s crossed every soon to be hitched guy’s mind…but some great laughs along the way.

8. Tin Cup

The perfect date night movie.  Golf, romance, and Cheech Marin.  Costner plays a washed up golf pro trying to get a handle on his game both on the course and off.  Renee Russo is a love interest and shrink that can help him get back on track.

7. Singles

The soundtrack alone to this film is the best of the 90’s.  Poking fun at and embracing the grunge scene of mid 90’s Seattle, Bridget Fonda and others hit their mark.  While combat boots and black leather jackets are the uniform of the day, it’s not just the rockers that make this story come to life.

6. She’s the One

New York’s favorite son’s follow up to his indie darling, Brothers McMullen.  Ed Burns masterfully crafts a tale of brotherly love and hate, portraying the Irish American family as only he can do.  Not only writing, but playing an always-broke cabbie, Burns gives an enlightening and humorous look at the double-edged sword of a tight knit family.

5.  Two if by Sea

Sandra does it again here as the understanding and fed up girlfriend of a low level thief played by Denis Leary.  His strong and obnoxious character wants to make his girl happy, but he also needs to pay the bills.  Wanting more for the two of them, getting more is cause for quite a few pickles they need to work out of.

4.  Chasing Amy

The king of bringing to life the side of life rarely noticed, Kevin Smith plays with one of the more interesting romantic twists in 90’s rom-coms.  Deep at times, and light at others, Ben Affleck is chasing something he can’t have.

3.  American Pie

Over the top humor, over the top hot love interest, and right on key for hormone laden teens in the height of puberty, American Pie is one of those movies that instantly became part of American moviegoer’s consciousness.  None of us looked at apple pie the same way again.

2.  The Wedding Singer

Some of the best jokes are those not told but shown.  Images of the ridiculous 80’s move this story along as one that would melt the coldest of hearts.  Adam Sandler instantly has the whole audience cheering him on as Drew Barrymore again, has every guy watching eating out of the palm of her hand.

1.  There’s Something About Mary

Franks and Beans! Fourteen years later and dropping lines from this classic still gets an instant laugh.  The second of the brilliant Farrelly Brothers library gives some of the best laughs to date for any romantic comedy.


Mike Dean