Sugar Ray — "Fly"

Sugar Ray came up as a funk-metal band, and frontman Mark McGrath was committed to the heavy stuff—he "wanted to scream and yell." So when "Fly" emerged, breezy and almost whispered, McGrath resisted the direction until director McG talked him into it, joking that the alternative was working at Del Taco. The gamble rebuilt the band overnight, and McGrath's frosted tips became one of the defining looks of late-'90s pop culture.

Released May 16, 1997, from the album Floored—which carries the song twice, once with reggae legend Super Cat and once without—"Fly" dominated radio immediately: #1 on the Hot 100 Airplay chart for four consecutive weeks, #1 on Modern Rock Tracks for eight weeks, and #1 in Canada. But it never appeared on the Billboard Hot 100 at all: with no commercial single released, album cuts weren't eligible under that era's chart rules, making "Fly" one of the decade's biggest radio songs with no Hot 100 line to show for it. McGrath pointed out the trick that made it work—stark imagery about death and the loss of a mother tucked under an impossibly sunny melody everyone sang along to anyway.

VH1 later ranked "Fly" #52 among the 100 greatest songs of the '90s. Sugar Ray kept making hits, but this was the hinge: the moment a band built to scream discovered it was better at summer.