100. E-Mail My Heart (1999)

(White)

Album: …Baby One More Time

Hear me out – “E-Mail My Heart” is a great song. Yes, it’s totally sappy, and yes, lyrically it dates itself squarely within a post-internet but pre-texting era (and is a little stalker-ish!), but… those vocals! Many will deny it now, but more than a few millennials have definitely belted this song in their bedrooms without any hint of irony. Culturally, we’ve allowed songs like “Sealed with a Kiss” (not to be confused with Spears’s own 2011 song “Seal It with a Kiss”) and “Groovy Kind of Love” enter the pop lexicon. “E-Mail My Heart” deserves its place as well.