Coming up on eight years later, I remain baffled that Rosemarie DeWitt didn't get an Oscar nomination for her performance as the eponymous Rachel, though at least co-star Anne Hathaway got a nod as Rachel's sister, the fresh-out-of-rehab powder keg Kym. Rachel Getting Married is easily the darkest movie in this list, but its intimate examination of the shifting dynamics of a broken family make it worth a watch.
Bridesmaids has everything: rowdy, raunchy, and hilarious comedy centering on female friendships, an engaging romantic subplot, Kristen Wiig doing an impression of a penis, puppies wearing berets, Wilson Phillips, and Melissa McCarthy's breakout, Oscar-nominated performance.
I recently saw Four Weddings for the first time in years and I was surprised by how well it's held up. Even factoring in the way that Hugh Grant's performance here became a template for years' worth of his performances going forward (until he transitioned to a "bad boy" persona), Four Weddings is still a disarmingly charming movie.
Be it the 1950 version starring Spencer Tracy, Elizabeth Taylor, and Joan Bennett, or the 1991 version starring Steve Martin, Diane Keaton, and Kimberly Williams, Father of the Bride tells a (self-explanatory) story with a lot of warmth and comedy.
Cary Grant. Katharine Hepburn. James Stewart. You just can't go wrong with The Philadelphia Story, a movie about a woman who's all set to marry one man, temporarily falls for another, and then ends up remarrying her ex-husband. It's yar.