Now: Pregnant pop star and No Doubt diva
Then: Fashion disaster fronting a wacky junkyard-ska troupe that really, really liked Was (Not Was)' "Walk the Dinosaur"
Unintentional hilarity: Gwen's Kriss Kross-inspired backward overalls and geek-chic dance moves
Redeeming quality: Her Betty Boop-meets-Cyndi Lauper vox stole the show even then.
Now: Flame-haired, piano-playin' mom and storyteller
Then: Trying to make ends meet by "acting/singing" in a TV commercial for Kellogg's Just Right cereal.
Unintentional hilarity: Where to start? Amos' creepy, orgasmic enthusiasm for a spoonful of the stuff or the painfully '80s ad jingle?
Redeeming quality: Mmmm, breakfast cereal.
Maynard James Keenan
Now: The dark underlord of twisted prog-metallers Tool
Then: Intense mullethead fronting a garden-variety new-wave rock band.
Unintentional hilarity: A toss-up between his skintight leotard and the spoken-word slam-poet breakdown in the middle, featuring mic echo on the word free.
Redeeming quality: Makes Keenan seem much less threatening today.
Now: The biggest rock-and-roll band in the world
Then: Skinny rockers roaring through "The Fool" a blistering early original akin to early Echo & the Bunnymen on an Irish talk show.
Unintentional hilarity: One of the critics describes U2's sound as "a curious amalgam of heavy metal and new wave and maybe a Bowie influence in there, too."
Redeeming quality: Besides the fantastic song? Well, the band's youthful enthusiasm and bright-eyed energy are impossibly infectious.
Now: Influential alt-poets who still tug at the heartstrings live.
Then: Camera-shy college rockers debuting with their first music video, the now-disowned "Wolves, Lower."
Unintentional hilarity: The awkward angles, slow motion, dim lighting and artsy freeze frames make the clip appear to be a chin-stroking student's disastrous senior thesis.
Redeeming quality: Again, the tune. Its burnt-orange jangle and cryptic lyrics still burn with mystery and optimism today.