Britney Spears "Lucky" (2000)
Album: Oops!...I Did It Again
Once upon a time, before the shaved-head incident and the backup dancer baby daddy, Britney Spears's life was actually enviable. She was a pop princess dating a boy band prince, had a ridiculously hot body and still bore resemblance to the innocent schoolgirl we all felt ashamed to lust after. This song, an instant pop hit sharing album space with arguably her most iconic song to date, "Oops!... I Did It Again", foreshadowed that life at the top of the pop charts was all about mastering a façade, and keeping up an act of impermeability while exceeding expectations would be difficult to maintain.
Not that any of us could even fathom a public life in the crosshairs of ravenous paparazzi, but this song, however riddled with classic repeat-after-me singalong pop-bait, spoke to each of us that knew our lives were messier behind closed doors. Whether you were the stereotypical prom king or the stoner loner, you loved this song because, at the end of the day, "Lucky" was pure angst hiding behind a white picket fence ready to crumble. Case in point: the year 2007, when she lost her shit and self-inflicted baldness on purpose. This song, though, still knocks. -Brianne Garcia