I went with "The Good Life" off of the band's dynamite, yet commercially unsuccessful, second album, Pinkerton. Released in 1996, Pinkerton is awesome, but I honestly had no idea it was released until many years later. For whatever reason, it didn't resonate with mainstream radio or MTV, but it has since gained cult status and critical acclaim.
"The Good Life" was the second single released off of Pinkerton, released on my 19th birthday. Presumably, "The Good Life" did not puke up a bunch of Icehouse off of a balcony at an off-campus party that night, but I sure as hell did. God, I miss college. Anyway, "The Good Life" peaked at #32 on Billboard's Modern Rock Tracks chart, making it the least successful Weezer single released up to that point. It's a shame, too, because it's a great song -- the kind of catchy, yet rocking, power pop you've come to expect from Weezer.
The video is directed by Jonathan Dayton and Valerie Faris, who have directed a ton of great music videos (including "Been Caught Stealing" by Jane's Addiction, "Tonight, Tonight" and "1979" by The Smashing Pumpkins, and many Red Hot Chili Peppers videos) as well as the 2006 comedy Little Miss Sunshine. Starring in "The Good Life" is a young Mary Lynn Rajskub, who went on to star as Chloe O'Brian in 24 (among many other acting credits).