Top 25 Wedding Movies of All-Time (20-16)

Movies have a way of drawing us in and touching our emotions. Today, we’re rediscovering some of our favorite wedding movies. If you’re looking to take a break from all that stressful wedding planning, the best way to “forget about it” for a little while is to rent or download a wedding movie and get lost in the story of the film for a couple of hours.

If you missed numbers 25-21, you should check those out before you read through these by starting at the beginning of our wedding movies list.

Top 25 Wedding Movies of All-Time

20The Wood
The Wood is a 1999 romantic comedy, written by Rick Famuyiwa and Todd Boyd. Famuyiwa also directed the film, which stars Omar Epps, Richard T. Jones, and Taye Diggs. This is one of those movies that fellas can sit through – it has a nice story line for your groom, so don’t be shy about making him watch this one.

The Wood, i.e. Inglewood, is home to the main characters Mike, Slim, and Roland… best friends since junior high. Hours before the wedding is set to take place, they recall key moments of their friendship and the rites of passage of boys to men in flashbacks.

In addition to male friendship and wedding-day jitters, the story explores Mike’s long-term connection to Alicia, his first sweetheart.

19The Best Man
The Best Man is a 1999 romantic comedy/drama. It is written and directed by Malcolm D. Lee and was produced by Spike Lee’s production company. The film stars Taye Diggs, Nia Long, Morris Chestnut and Sanaa Lathan.

This is one of those movie’s we recommend watching around the holidays because of its festive feel. Taye Diggs and Nia Long really bring out the best in each other, and we really like this film because its fun and entertaining.

18The Proposal
Sandra Bullock and Ryan Reynolds light up the screen in this 2009 romantic comedy. Bullock plays Margaret Tate, a socially inept Chief Editor at a major New York City book company who, in order to avoid being deported to Canada for a year because of a visa transgression, comes up with an idea of marrying her American assistant, Andrew Paxton.

Andrew Paxton is played by Ryan Reynolds. The character is a good-hearted assistant to Margaret who wishes to be promoted to editor and have his chosen manuscript published. He agrees to the fake marriage on the terms that those two conditions are met. All in all, this is a refreshingly entertaining comedy that is highly recommended.

17Four Weddings and a Funeral
If you haven’t seen this 1994 film directed by Mike Newell and starring Hugh Grant and Andie MacDowell, then you are in for a treat.

The film follows the fortunes of Charles (Hugh Grant) and his friends as they wonder if they will ever find true love and marry. Charles thinks he’s found “Miss Right” in Carrie, an American. This British subtle comedy revolves around Charlie, his friends and the four weddings and one funeral which they attend.

The film also features a lovely soundtrack with classics like Chapel of Love, Stand By Your Man, and Can’t Smile Without You.

16The Wedding Date
The Wedding Date is a 2005 romantic comedy directed by Clare Kilner. The release was successful achieving $47 million worldwide at the box office against a budget of $15 million. It is based on the book Asking For Trouble by Elizabeth Young.

Kat Ellis, played by Debra Messing, is a single New Yorker who returns to her parents’ house in London to be the maid of honor at her younger half sister’s (Amy Adams) wedding. The best man is none other than her former fiancé, who unceremoniously dumped her two years ago.

Anxious about confronting him and eager to impress him, she hires debonair male escort Nick Mercer (Dermot Mulroney) to pose as her boyfriend. Ladies – this is such a touching movie and we think you will really enjoy watching it while curled up next to your fiancé.

The List Gets Better… up next #15-#11

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