90s Pop

Four TRL-era pop singles on a comfortable ten-second clock. If you owned a CD changer or watched a music video on a Friday afternoon between 1996 and 1999, this should be a clean sweep.

Late-90s pop was an industry phenomenon — boy bands, girl groups, teen pop solo acts, and R&B crossover all running on parallel tracks at the same time. This four-song set picks one signature single from each lane.

Backstreet Boys' "I Want It That Way" (1999) is the boy-band ballad in its purest form: Max Martin's hook-stacked production, AJ McLean and Brian Littrell trading verses, lyrics that are technically nonsense if you read them carefully and devastatingly catchy if you don't. It's also the song most often cited when people argue Max Martin invented modern pop melody — the first half of the chorus is a textbook example of his "melodic math."

Britney Spears' "...Baby One More Time" (1998) launched both Spears's career and the late-90s teen-pop boom that ran for the next four years. The track was originally pitched to TLC, who passed; it ended up at Jive with a new vocal performance and a four-on-the-floor pulse that sounded built for radio. The schoolgirl music video did the rest.

Spice Girls' "Wannabe" (1996) hit a year or two earlier and is the song that proved girl-power could outsell almost anything when it had a hook this stupid-good. Recorded in about an hour, the verse-chorus structure is barely a structure — it's mostly a chant — and that's why it works.

TLC's "No Scrubs" (1999) is the album-of-the-year-grade R&B record on this list. The Kandi Burruss / Tameka Cottle / Kevin "She'kspere" Briggs production sits on a chunky guitar loop and a beat that influenced what radio sounded like for the next two years. Lisa "Left Eye" Lopes's rap break is one of the great pop-R&B verses of the decade.

Four songs, four different strands of the same era. The Easy variant gives you a comfortable ten-second clip to place each one; the Hard variant cuts the window down to three seconds, which is enough for any of these if you grew up on TRL and almost impossible if you didn't. Pick your difficulty and find out.