Britney Spears – “Sometimes” – (1999)

This was Britney’s second single and while it was nowhere near as successful as the title track from …Baby One More Time, it almost cracked the top 20 in the U.S., peaking at #21. The music video was a TRL mainstay for the duration of its eligibility – and let’s be honest, Billboard’s inconsistent and screwy chart rules in the mid and late-90s made it so TRL was almost a more recognizable form of song popularity. The video features really lame choreography because Britney was nursing a wounded knee during its shoot. It’s basically Britney in white showing that she was “pure” – in contrast to the “Baby One More Time” video which was kind of the opposite. This song might be kind of annoying today but back in 1999 it was just another pop hit.