Gilbert O’Sullivan is a curious character, a McCartney-esque singer/songwriter with a predilection for whimsy who had a big, big hit with “Along Again (Naturally),” along with a few smaller singles in the early ’70s, but who kept working steadily into the new millennium, turning out a body of work that is remarkably of a piece. While production styles certainly changed from his 1971 debut Himself to his 2001 record Irlish, his songwriting didn’t change all that much — he remained dedicated to his two signatures of maudlin ballads and sing-songy up-tempo tunes, both couched in vaudevillian theatrically, unrelenting whimsy, cutesy verse, a surprisingly dark undercurrent of despair, and hints of misogyny. It was a bizarre mix, but only if you concentrated closely — on the surface, it skips by on his cheerful melodies, outright jokes, and sentimental streaks. Yet when examined on a large scale, it’s hard not to notice the bunch of contradictions that make O’Sullivan such a curious artist. And there is no greater scale than Caricature: The Box, a lengthy three-disc retrospective released in a limited-edition from Rhino Handmade in early 2004 that covers all three decades of his career in equal measure. Since Gilbert O’Sullivan’s career as a hitmaker of note ended in 1975, just three years after his debut, that’s leaves a lot of room for recordings unheard by anyone outside of the decade — namely, nearly two discs’ worth, since all the hits are on the first 25-track disc of this set. As the collection rolls on, the traits that are charming, even irresistible on the first collection — the soft, sulking melancholy of “Nothing Rhymed” and “Alone Again (Naturally),” the sweetness of “Clair,” the irrepressible stiff-backed boogie of “Get Down,” the cheekiness of writing introductions to each side of his LP — take on a different, slightly sour flavor. The melodies, once ingratiating, turn irritating; the reflective ballads seem self-pitying; the introductions, which can inspire a chuckle, grate. Worst of all, the cleverness turns mean-spirited — compare the light-footed “Matrimony” to “The Marriage Machine” or “A Woman’s Place” (“is in the home,” naturally), two nasty pieces of work cloaked in catchy melodies (and this isn’t even counting “Can’t Think Straight,” a duet with Peggy Lee where he slaps her). These developments make for interesting listening, as does hearing O’Sullivan’s music stay the same as the production changes, but interesting isn’t always compelling, and only the already-converted will find this compelling listening from beginning to end. Those who aren’t fascinated by his peculiar world view will be satisfied by Rhino’s 1991 The Best of Gilbert O’Sullivan, which contains all the highlights from this set in a mere 20 tracks, which is precisely enough time for O’Sullivan’s gifts to be charming and endearing. This set, while providing an accurate career overview for the dedicated, is simply too much for anybody else.