By 2004, Hilary Duff was one of the more popular young stars on the planet, having enjoyed success on television (as the star of the Disney Channel's 'Lizzie McGuire' series), in theaters (with a budding film career that included a role in 'Agent Cody Banks') and on the pop charts, where she'd enjoyed a string of moderate hit singles. None of this, however, qualified her to cover the Who's 'My Generation.'

As we've seen in our Terrible Classic Rock Covers series, there are plenty of ways to mess things up when an artist tries putting their personal stamp on a song everyone knows by heart. Sometimes, what seems like a good idea on paper just doesn't work out in the studio. On the other hand, you don't always need to roll tape to find out than an artist has no business going near a song, and that's definitely the case with Duff and 'My Generation.' A squeaky-clean teenage Disney starlet with a paper-thin voice, Duff had neither the life experience nor the vocal chops to handle the material; in fact, she reportedly only covered the song (and started playing it live) because her manager was a fan of the Who.

Sadly, no one involved with Duff's 'Generation' was enough of a Who fan to prevent the recording of this cover's soulless backing track, which scrubs out the original's nihilistic aggression and replaces it with clattering drum machines, tinny guitars and drab synths, all squashed up against a busy background vocal arrangement that seems designed to disguise (or perhaps drown out) Duff's voice.

Not that there would have been anything wrong with that. Singing with all the passion and urgency of a driving school instructor, Duff sounds like she might be reading the lyrics for the first time -- lyrics that, by the way, were given an obnoxious revision, reversing one of the most brilliantly spiteful lines in rock history and leaving Duff to chirp, "Hope I don't die before I get old."

To her credit, Duff seemed to sense that her sanitized brand of tween pop might be an artistic dead end. "When you are under the control of a label, you don't always get to have the sound you like," she complained to writer Jim DeRogatis in 2005. "If I could change it, I would, and it would sound [less pop]. My name is Hilary Duff, and I don't know why I don't get to make Hilary Duff music."

In recent years, she's recorded more sporadically, and lifted from slightly more sensible artists (in 2008, she released the Depeche Mode-inspired 'Reach Out'). And while her records don't sell anywhere near as well as they did during her early-aughts heyday, she seems happy to make the trade-off in the name of increased independence. Chalk Duff's 'My Generation' up to youthful indiscretion, and let it be a lesson to any producer or manager who ever gets the bright idea to let a teenage starlet try and tackle one of classic rock's finest.

Listen to the Who's 'My Generation'

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