59. 27 Dresses (2008)- Anne Fletcher

27 Dresses Trailer

Always a bridesmaid, never a bride. Jane (Katherine Heigl) has embodied this phrase ever since her first wedding when she was a little girl just after her mother died. She had to step in and save the day when the bride's dress ripped all down the back. Ever since then she has been a bridesmaid or maid of honor in 27 weddings (all of which had hideously nasty dresses that the selfish brides forced her to wear..."don't worry you can always shorten it and wear it again." yeah okay). Constantly out shadowed by the brides, Jane is a workaholic mainly because of her sitcom perfect boss, George (Edward Burns). This quickly becomes an underdog story, seeing as George falls in lust with Jane's younger, beautiful, rebellious sister Tess (Malin Akerman) who just happens to bug the shit out of you and who you want to slap across the face and tell her to "grow up! the entire movie. Jane's saving grace through all of the annoying situations with her sister are the commitment columns in her local newspaper written by a Mr. Malcom Doyle (James Marsden). This movie is definitely well written and a total "chick flick," but...
I did have two of my guy friends willingly watching it with me, rooting for Jane along her journey to finally become the person that she has helped so many times during her life- the bride, so go figure!