Bob Dylan, "Like a Rolling Stone". An obvious cheat ... the video is from 1966, the famous "Judas" version. The concert was officially released in 1998. Play fucking loud, indeed.
Madonna, "Ray of Light". At 40, she reinvents herself again, and makes arguably her best album in a decade that isn't called The Immaculate Collection.
Lauryn Hill, "Doo Wop (That Thing)". Her first post-Fugees solo album turned out to be her one and only studio album (so far).
Neutral Milk Hotel, "Holland, 1945". Their second album turned out the be their last studio album (so far). Jeff Mangum has gone on to other things, none of which includes a solo studio album.
Lucinda Williams, "Car Wheels on a Gravel Road". There are some divas on this list ... Madonna and Cher come to mind. Lucinda Williams is the anti-diva: she drips authenticity.
OutKast, "Rosa Parks". OutKast had a tremendous series of albums to start their career. This song got them sued by Rosa Parks.
Air, "All I Need". The opposite of OutKast, Air's first album was their best. I'm just making this up, I have nothing to say about this band.
Brandy and Monica, "The Boy Is Mine". Brandy is Snoop Dogg's cousin. Monica released an album, All Eyez on Me, with the same title as a Tupac album.
Cher, "Believe". I told you there were divas on this list. She's the only who was in her 50s at the time. This wasn't the first time Auto-Tune raised its head, but it's the one we remember.
Massive Attack, "Teardrop". A.K.A. " Theme from House".