Lisa Loeb “Stay (I Missed You)” (1994)
Directed by: Ethan Hawke
Also directed videos for: N/A
Complex says: Okay fine, "Stay" is a bit corny. But it's also a '90s pop classic that's got an interesting story behind it. Ethan Hawke befriended Lisa Loeb and passed her demo to Ben Stiller, who was directing Reality Bites at the time. The song ended up on the film's ending credits as well as its soundtrack, which helped Loeb become the only person to ever have a Number one single on the Billboard charts without having any sort of record deal. Hawke also directed the video, which was rather impressive considering it was a single shot video.