Tanglewood's warm reception and the Jews' lauded first foray into live performance and touring must certainly have been a balm to Berman's much-publicized bouts with depression and addiction, if Lookout's opener "What Is Not But Could Be If" is any indication. The lyrics point to focusing on new beginnings rather than dwelling on the errors of the past, yet the stilted wording and Berman's melancholic delivery don't make a very convincing case. It's a weak song and not a great choice to begin the album, no matter how thematically desirable it may seem. The stronger "Strange Victory, Strange Defeat" with its purposeful ambiguity would have been better.
The poor start does this album a disservice, because immediately afterwards follows its strongest stretch of material, beginning with the fiery "Aloysius, Bluegrass Drummer." Berman's wife, Cassie, has taken on a more prominent role on this and the last album, and here she gets the chorus on the album's strongest track, "Suffering Jukebox." Her voice is a nice complement to Berman's both here and when it is a hazy background element on the Maher Shalal Hash Baz cover "Open Field." "My Pillow Is the Threshold" is one of the album's more serious, darker tracks, ending with eerie clouds of ambient feedback. "We Could Be Looking for the Same Thing" is a fairly conventional but nonetheless effectively sweet song that should send pangs of jealousy throughout the group's Nashville peers.
The only section other than the opener that isn't so great is a sequence toward the end. "San Francisco B.C." has an enjoyable energy, funny lyrics, and good music, but "Candy Jail," coming right on its heels, seems like a jokey novelty in comparison with its "peppermint bars, peanut brittle bunk beds, and marshmallow walls." It's as insubstantial as, well, cotton candy, and the subsequent "Party Barge," complete with watery engine sounds, seagulls, and foghorn, doesn't fare much better. With so many humorous songs in a row, the effect is too light and too easy to dismiss.
The layers of guitars and voices, especially Cassie's, are particularly well done on this album, and for the most part, the writing is as strong as ever. Apart from a weak track and an unfortunate string of fluff, Lookout Mountain, Lookout Sea has strong moments that rival the best of Berman's work.
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