Greatest Hits: My Prerogative appeared at the tail end of a year where Britney Spears was married twice, canceled a tour, injured her knee, lost the movie role of Daisy Duke to rival teen pop diva Jessica Simpson, was a punch line in Fahrenheit 9/11, and had countless paparazzi shots of her drinking and making out in public. It was enough high-profile shenanigans for a career, and it was par for the course for Britney, who hadn't been out of the pop culture headlines since she released her debut album, ...Baby One More Time, in January 1999. In the nearly six years separating that debut album and the release of Greatest Hits in November 2004, Britney was omnipresent, representing both the entire teen pop phenomenon of the turn of the millennium, plus the teasing, Maxim-fueled sexuality of the time; it's not for nothing that Tom Wolfe name drops Britney Spears, not archrival Christina Aguilera, in his 2004 novel I Am Charlotte Simmons -- Britney alone captured the era, which in turn is captured on this 17-track hits collection. If Bob Dylan had a hard time being a voice of a generation (which he does acknowledge in his autobiography, Chronicles), imagine the weight put upon this simple Louisiana girl who just wanted to be famous and became a cultural icon instead! During those six years, she kept turning out product, selling herself with increasingly racy photographs, all the while being used as an example of everything that's wrong with pop culture, or even worse, as the subject of cultural theses explaining pop culture. No wonder that after six years of mind-boggling fame she wanted to abandon her career for motherhood -- it's exhausting being in the limelight, even for a shameless pop star! So, Greatest Hits arrived at a perfect time -- just as her star was fading, just as the teen pop era grew to a close, and just as she readied herself for retirement.
As a time capsule, Greatest Hits does its job well. It has all of her hits outside of "From the Bottom of My Broken Heart," a largely forgotten ballad from her debut released just before her second album, Oops!...I Did It Again, and it contains two very good previously unreleased tunes, including the In the Zone outtake "I've Just Begun (Having My Fun)," an infectious spin on No Doubt's "Hella Good" that betters most of the songs that were featured on the album (it also has a useless remake of Bobby Brown's "My Prerogative," which seems to exist solely for its video). Clearly, this is the album not just for the casual fan, but for any fan of Spears, because like most teen pop singers, her albums are notoriously spotty affairs, memorable largely for the singles themselves. What is surprising is that those singles -- all presented here in their hit forms, which means this has the "Stop Remix" of "(You Drive Me) Crazy," not the album version -- are somewhat less than the sum of their parts when collected together. The similarities in Max Martin's clanking, insistent writing and production become blindingly evident, and Britney's thin, squeaky voice wears thin over the course of 17 songs. Also, the song selection and sequencing emphasize keeping the perfect beat over chronology, which not only makes it a little harder to listen to as an album, it puts the focus on the individual songs, which seem neither as hooky or catchy as they did when they were initially on the radio. There are exceptions to the rule, of course -- "...Baby One More Time" still retains its punch, "Oops!...I Did It Again" is so silly it's hard to resist, "(You Drive Me) Crazy" is fluffy dance-pop at its best, and "Toxic" is a delirious, intoxicating rush -- but they're all better as individual moments, even if when taken together, they do illustrate the cacophonous monotony of her music and, yes, her time quite well. So, even if it isn't a great listen as a cohesive album, Greatest Hits does perform the valuable function of offering all of Britney's hits in one place, and it does work as a portrait of the time when Britney Spears was the defining figure of American pop culture. But if you compare it to The Immaculate Collection, which captured the time when Madonna was the defining figure of American pop culture and does work as an album, it's clear that a cultural artifact isn't necessarily the same thing as great music.