How, exactly, does Ashlee Simpson have a career? What kind of amazing deal with the devil did she strike to remain popular after the Saturday Night Live fiasco of 2004, or after the Orange Bowl debacle of 2005, or the Marie Claire hypocrisy of 2006? She has somehow managed to remain on the scene longer than she ever deserved, but she certainly hasn’t developed any more musical talent – Bittersweet World is proof.

Simpson experimented with an ’80s sound on sophomore album I Am Me, and that influence (guided by producers such as Timbaland and The Neptunes) stuck around for Bittersweet World, which includes a variety of ballads and pop-rock tracks. Too bad most of them fail.

Simpson’s voice – sometimes nasal, often pushed past its very limited range – is inexcusably annoying on Bittersweet World and often deteriorates into a buzzing drone.

Her songs seem to be self-affirmation of her own awesomeness (“I know I’m hot stuff,” she whines on “Hot Stuff”), an attack on haters (“I’ve just begun to find my way,” she proclaims on “What I’ve Become,” basically a musical middle finger to the paparazzi) or an experiment in just how emo she can be (“Don’t you see my black tears?” she asks on “Ragdoll”). There are no surprises here – just one formulaic track after another.

The album begins with single “Outta My Head,” probably the only tolerable track on the entire album – but it’s basically a Gwen Stefani knock-off. Over a very punchy bass-line and keyboard riff, Simpson sings the disturbingly catchy hook and chorus: “All I ever hear is ay ya ya ya ya/ You’re talking way too much/ I can’t even hear me now/ All this noise is messing with my head/ You’re in my head, get outta my head/ Outta my, outta my head.”

On its own, the song is nothing special. But compared to the other tracks on this album, it’s utter gold. At least, it’s far better than the title track (which seems to have completely stolen its instrumentation from Soft Cell’s “Tainted Love”) or “No Time for Tears,” which goes absolutely nowhere, has no memorable lyrics and is utterly forgettable.

And what’s even more disappointing is some of these songs definitely show promise. “Boys” is a super cheeky slice of pop-rock, and it’s on the same level of sass as Madonna’s earlier work, especially with the amusing-but-trite lines, “Use your head, but not that one/ One-track mind, one-track mind, one-track mind.” But Ashlee can’t seem to knock it out of the park. Her vocals fall flat, and the song is a pale shadow of what it could have been in the hands of better artists.

Similarly ho-hum is “Never Dream Alone,” the album’s requisite ballad. The song’s stripped-down quality (vocals, piano, strings) is appealing, and even the lyrics aren’t that bad: “Fall asleep with my hand on your heart/ I won’t let it skip a beat.” However, the problem is again Simpson’s voice – her vocals sound stretched to their limit, even though the song doesn’t ask for anything too range intensive.

Overall, Bittersweet World is an album hindered by the shortcomings of its creator. As a vocalist, Simpson just doesn’t have what it takes to make her songs shine. As a lyricist, she’s prone to clichés that belittle the messages she’s trying to send. On one of the album’s tracks, Simpson sings, “They say I get away with murder” – and with the subpar quality of Bittersweet World, she has.

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RATING: 2.5 STARS OUT OF 5