My Best Friend's Wedding is one of the first wedding-based films that Dermot Mulroney participated in, and it also happens to be the most fun. Featuring Julia Roberts in her glorious late-90s heyday, rarely has the build-up to nuptials been more chaotic albeit more enjoyable on screen. As most people know by now, My Best Friend's Wedding revolves around Roberts' Jules, who realizes that she is in love with her best friend Michael (Mulroney) when he is on the cusp of getting married. She spends nearly the entire time attempting to break up the wedding, engaging in such nefarious actions as attempting to humiliate Michael's fiance Kim (played by the then very young Cameron Diaz) at karaoke, or by passing off her gay best friend George (a hilarious Rupert Everett) as her boyfriend in a attempt to make Michael jealous. What all of this silliness gets at however is some very truthful emotion. Very rarely does someone act on their reservations about a couple, or take it to the extremes that Roberts' character does. And yet, quite often weddings are far from an idyllic ceremony, where every person in attendance is unified and supportive of the two people preparing to take the plunge.