The Wedding Singer, 1998

Who: Drew Barrymore, Adam Sandler
What: Be-mulleted 80s singer Robbie (Sandler) dreamed of being a rock star but now belts out other peoples’ hits at wedding receptions. Meanwhile, Julia (Barrymore) waits tables at the same events. They’re both with other people until Robbie is jilted at the altar and Julia starts to wonder if she’s engaged to the wrong man.
Defining moment: Robbie playing a song he wrote to Julia, half of which he wrote while he was with his ex, and half after she dumped him.