Cruel Intentions‘ Sarah Michelle Gellar and Selma Blair became the first same-sex pair to take home the award in 2000, and they made sure their red carpet pics turned out just as steamy as their film kiss. This set a precedent for plenty of female pairs (and trios) to be nominated throughout the decade, including for Starsky & Hutch and Not Another Teen Movie.
The exceptions, though, were important. Brokeback Mountain won in 2006, making Jake Gyllenhaal and Heath Ledger the first men to win together, and Milk‘s Sean Penn and James Franco saw a nomination in 2009. Of course, the 2000s “two dudes kissing lol” trope also saw wins for American Pie 2 and Talladega Nights: The Ballad of Ricky Bobby.
But everyone knows that what happened in 2005, when real-life lovebirds Ryan Gosling and Rachel McAdams ran across the entire stage before embracing in an unfurling display of passion to recreate their rain kiss from The Notebook, is and will always be the apex of Best Kiss. Everyone else can go home.