It’s a fascinating bit, really: co-founding member (with former husband Jim Mathus) of retro swing band Squirrel Nut Zippers, who sold a million-plus albums in 1997 thanks to the strangely successful single “Hell” (on which she was not featured) and follow-up single “Put a Lid On” (on which she was), Katharine Whalen was the voice to be reckoned with in the roaring ‘90s swing scene. Nowhere is this more evident than on the band’s third, and penultimate, proper album on which she delivered a searing, vulnerable yet sly vocal on “Low Down Man”, a balance of which garnered comparisons to Billie Holiday.

Those comparisons were furthered, and moderately played against, on her 1999 solo debut Katharine Whalen’s Jazz Squad. Artistic restriction, the need to be an original “true” voice, boredom, who knows, but for one reason or another, Whalen disliked the pigeonholing. Having not recorded in seven years, Whalen releases her sophomore solo album, and it appears that she has successfully, and entirely, shaken the Holiday/breathy chanteuse aesthetic. Gone is the jazz backing band, gone are the standards and songs written to sound like standards, gone is husband Mathus, gone is, essentially, anything linking Whalen artistically, and perhaps personally, to her past.

Thus, Dirty Little Secret is a reinvention. Whalen co-writes lyrics for seven songs (a first), while David Sale (of San Diego based-band Camus) produces, writes or co-writes every lyric, and plays or programs every instrument. It is strange that Sale doesn’t get more billing, as this could very well be a trip-hop album with a producer-as-auteur who merely enlisted Whalen for vocal duties. In any event, the album is an experiment in pop music, to say the least. Anachronistic musical tracks that sound like a cross between Latin, sampled jazz, and the Motown Remixed series paired with Whalen’s hot vox make for intriguing, and highly welcome, bedfellows.

The artistic risk is highly laudable; the results, however, are highly uneven. With the exception of the title track, an unthreatening but enjoyable little pop song, the first half of the disc is entirely overdone and stretched. Sadly, the album’s first half is at its best on the most straightforward songs (“Follow”, “Dirty Little Secret”). At its worst Whalen, or more accurately, Sale, misses terribly, with “The Funnest Game” coming off like Shakira with lesser production values and “You-Who” sounding like something off Radio Disney.  With the exception of “Three Blind Mice”, which sounds like a reworking of “Hell” (ouch, I know), the second half of the album gets quite interesting—though if you are waiting for her delectable voice to cut loose, you’ll have to wait for the next album.

But beginning with track seven, there is a run of four straight songs that make the album worthwhile. There is the dark production and intense yet sexy vocals of “Angel”, the jazz-ish piano and melodic flow of “Want You Back”, “Long” (which is Whalen’s best vocal performance of the album), and also one of the best combinations of Whalen and Sale’s approach to pop structure wedded together on “In the Night”. These songs merit attention, whereas the rest of the album is forgettable pop or ineffective—make that, unaffecting—experimentation.

If Whalen wants to pursue more sonically and artistically ambitious “jazz”, as she hints at here, or you, dear reader, wish Whalen and Sale’s work was more adventurous, I must highlight the work of the incredible Mina Agossi (check out E-Z Pass to Brooklyn). She perfectly strikes the delicate balance of smoky jazz vocals with aggressive musical experimentation. As for now, Dirty Little Secret is the portrait of an artist striving to create new territory and find new forms and sounds, and ending up in that dreaded artistic purgatory: the middle.