I love stories centered around big events: anniversaries, funerals, and especially weddings. A large group of people — some who know each other intimately, some who don’t — in a close environment while emotions run high is a recipe for excellent drama. Here are some of my favorite chaotic wedding stories (wedding not guaranteed).
The Philadelphia Story (1940)
This list wouldn’t be complete without The Philadelphia Story, even if I wasn’t obsessed with it to a medically concerning degree. As the only film starring Katharine Hepburn, Cary Grant, and Jimmy Stewart together — directed by the iconic George Cukor, no less — it has a special place in film history. The entire story unfolds over the 48 hours leading up to a big society wedding. If you haven’t seen this classic, do yourself a favor and watch it tonight. To quote the wonderfully wise Liz Imbrie, “We all go haywire at times, and if we don’t, maybe we ought to.”
My Best Friend’s Wedding (1997)
Is this movie’s premise (a marriage pact dependent on the parties being unmarried by the ripe old age of 28) absolutely ridiculous? Yes! Is it still an absolute favorite of mine? Also yes! Julia Roberts stuns with loose curls and slightly masculine fashion, pure ’90s perfection as she makes horrible choice after horrible choice. Cameron Diaz, with her trademark smile, is an ingenue you can root for, and Rupert Everett charms as the dapper best friend of your dreams. Dermot Mulroney is also there. The ending is one of my favorites of all time. It holds up in all the ways that matter.
Imagine Me & You (2005)
If anyone could make me believe in love at first sight, it’s Piper Perabo and Lena Headey. While only the beginning of the film takes place at a wedding, said nuptials are so central to the plot, I’m counting it. Lesbian Luce (Headey) is Rachel’s wedding florist, and she locks eyes with bride Rachel (Perabo) as she heads down the aisle to marry Hector (Matthew Goode). The subsequent conflict runs the gamut from hilarious to heartbreaking, wrapping up in a way that’s certified romance gold. As they say: Never let your husband stop you from finding your wife.
Mamma Mia (2008)
If anyone could make me believe in love at first sight, it’s Piper Perabo and Lena Headey. While only the beginning of the film takes place at a wedding, said nuptials are so central to the plot, I’m counting it. Lesbian Luce (Headey) is Rachel’s wedding florist, and she locks eyes with bride Rachel (Perabo) as she heads down the aisle to marry Hector (Matthew Goode). The subsequent conflict runs the gamut from hilarious to heartbreaking, wrapping up in a way that’s certified romance gold. As they say: Never let your husband stop you from finding your wife.
The Wedding Banquet (2025)
Angela (Kelly Marie Tran) and Lee (Lily Gladstone) are pursuing parenthood via IVF, but they’ve run out of money. Angela’s best friend Chris (Bowen Yang) and his boyfriend Min (Han Gi-chan) live in Lee’s family’s garage. Min’s visa is about to expire, but when he proposes to Chris, Chris is wary of outing Min to his conservative grandmother. Naturally, the solution to all their problems is for Angela to marry Min in exchange for Min financially supporting Lee’s fertility treatment. But when Min’s grandmother arrives unexpectedly, a modern marriage of convenience turns into a full-on farce. A pure delight.
The Drama (2026)
A polarizing film, and one I loved. Emma (Zendaya) and Charlie (Robert Pattinson) take “for better or for worse” as a challenge, and watching them unravel, together and apart, is riveting. While the titular drama is dark, the feeling I was left with as the credits rolled was decidedly light.
Seating Arrangements by Maggie Shipstead
This comedy of manners follows a dysfunctional hyper-WASPy family (is that redundant, or what?) over the weekend of one daughter’s summer wedding. Against all odds, the heavily pregnant bride-to-be is cool and collected, while her younger sister is going through post-breakup hell and their father is floundering in misery — mostly of his own making. There’s a rogue lobster, a beached whale, and — my favorite — golf cart–based carnage. Shipstead writes with sharp humor and sharper insight.
The Wedding People by Alison Espach
Phoebe comes to a seaside hotel to be alone, until unhinged bride-to-be Lila inserts herself into Phoebe’s life — or, rather, inserts Phoebe into her life. The relationship between Phoebe and Lila is bizarre, awkward, funny, tender, frustrating. A touch of romance, inconveniently timed for all parties involved, completes this portrait of a wedding gone sideways.
Three Days in June by Anne Tyler
The day before her daughter’s wedding, Gail loses her job and finds her ex-husband on her Baltimore doorstep with a cat she doesn’t want. Gail navigates wedding weekend drama with honesty and humor despite the difficult memories that resurface. I highly recommend the audiobook, performed by the incomparable J. Smith Cameron.
Kat Stoddard is the author of Wasp’s Nest.
Kat Stoddard lives with her daughter in Baltimore. Wasp’s Nest is her debut novel.
