"Ice Ice Baby"

Robert Van Winkle — Vanilla Ice — wrote "Ice Ice Baby" in 1983 at age 16, basing the lyrics on his experiences in South Florida. When Ichiban Records first released it, the song was the B-side to his cover of "Play That Funky Music" and went nowhere. Then DJ David Morales flipped the record, and heavy rotation of the video on The Box pushed the single into the mainstream while Van Winkle was still a face nobody knew.

Re-released by SBK Records on his debut album To the Extreme (1990), "Ice Ice Baby" became the first hip-hop single to top the Billboard Hot 100, and hit No. 1 in Australia and New Zealand for good measure. To the Extreme became the fastest-selling hip-hop album of its time. But the song's hook rode the unmistakable bassline of Queen and David Bowie's 1981 "Under Pressure" — and neither received songwriting credit or royalties until after the song became a hit. Rolling Stone later called the dispute a landmark music-copyright case, the sample-clearance cautionary tale an entire industry learned from.

Vanilla Ice was the first solo white American rapper to achieve commercial success, and he is credited — contentiously — with opening rap's mainstream door for the white rappers who followed, most notably Eminem. The backlash that followed his rise was as fast as the ascent, and "Ice Ice Baby" hardened into both punchline and time capsule: the exact sound of hip-hop crashing into the pop mainstream at the turn of the 1990s. Van Winkle himself kept wrestling with it, even re-recording the song as a nu-metal track called "Too Cold" on his album Hard to Swallow.