Despite its longer title, Oren Bloedow's second solo album is decidedly more straightforward than his eponymous debut. More surprising is the simple, supportive role played by his backing band, the jazzy groove trio Medeski, Martin & Wood. While tunes like "In the Clinch" and "100 Percent Live" offer more of the raucous funk from Bloedow's first album, mellow, emotional songs like "Endless Tears" and "Do I Have to Take You Outside" show a more introspective side to the songwriter. Bloedow's complex pop writing is still very much informed by the downtown jazz world he comes from, but the songs on The Luckiest Boy in the World sound less complicated and display great maturity and craft. Lyrically, Bloedow is less cryptic as well, and his voice sounds more confident than ever. Bloedow's excellent songs are perfectly matched by the often hypnotic groove created by drummer Billy Martin and bassist Chris Wood. Meanwhile, John Medeski adds tasty organ solos, but only when necessary. Guests like Ron Sunshine on harmonica and slide guitar virtuoso Dave Tronzo make the album one of the best avant pop albums to ever come out of the downtown New York scene.
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AllMusic Review by Matthew Carlin