In 2013 and 2015, drummer/composer/arranger John Hollenbeck released Songs I Like a Lot and Songs We Like a Lot, collaborations with the Frankfurt Radio Big Band and singers Kate McGarry and Theo Bleckmann. He mainly reworked relatively popular songs from the world of rock and pop into new and wondrous beasts on those shimmering and creative outings. On the first collection, his rearrangements of two Jimmy Webb tunes ("Wichita Lineman" and "The Moon Is a Harsh Mistress") broke my heart and stole the show, but almost everything sparkled.

For the follow-up, he asked McGarry and Bleckman to pick the songs, and she used pianist Uri Caine rather than keyboardist Gary Versace—and the result was perhaps even more astonishing. The Cyndi Lauper hit "True Colors" and the Carpenters' "Close to You" were transformed brilliantly. Still, I was stuck on the wonder of Hollenbeck's reconstruction of "Up, Up, and Away", with the band's horns playing a set of throbbing punches that combined Basie and Glass—only to have the arrangement then grow more transparent and magical from there. Both of these collections featured more obscure tracks as well, each interesting but not, perhaps, as hypnotic as the recasting of the more-known songs.

The trilogy is complete with Songs You Like a Lot, a third collaboration (with Versace back at the piano) with songs chosen by fans on the internet. As you might imagine, the compositions chosen for the final by fans are less quirky but very broad. There are songs here by Joni Mitchell, Peter Gabriel, James Taylor, Brian Wilson, and Bee Gees. But Hollenbeck's approach is equally explosive and dynamic, with every track blossoming into something that sounds almost wholly new.

As on the other recordings, there are tracks where the familiarity of the original version—usually a deeply-loved recording—might have been a barrier or enjoyment rather than the hook. Who covers "Wichita Lineman"? Who covers Joni's "Blue"? But both are masterpieces of imagination in Hollenbeck's hands. There is a mixture of reasons why Hollenbeck's reimagining beguile so much rather than rubbing our ears the wrong way, and "Blue" is a fine example of them all.

Most notably, Hollenbeck uses an "instrument" that is truly different than the one we typically associate with these originals, yet he manages not to disfigure our sense of the original. Joni's "Blue"—that hallowed song from her most bowed-down-to album, with its simply played piano plus voice and no more, thank you very much—was almost about its stripped-down clarity. Hollenbeck doesn't transform it with bombast—he's too sensitive an artist for that. But he brings the gentlest side of his big band, with an introduction in which electric organ and clarinet chase each other like squirrels on a lawn, leading to more than a dozen instruments weaving themselves into the song's familiar cascade of impressionist chords. Bleckmann's vocal enters, cushioned by an utterly careful arrangement that flutters with flutes and allows for a gorgeous brass counterpoint melody. It takes its time, it uses tempo carefully, it pauses and flows. Finally, it allows an insistent bass line to propel through to an ending section, with piano and mallet instruments providing the only percussion as it shifts harmonically between a few, yes, simple chords.

This song—and this arrangement—is a masterpiece. That an "orchestral" "Blue" could be this good seems miraculous. But that is the genius of Hollenbeck's project.

In his notes, the leader admits that he was afraid to mess too much with the original version of "Fire and Rain". As with "Blue", he uses the gentlest part of his arsenal, flutes, and chiming sounds, that circle in a Reich-ian manner, allowing McGarry to enter with James Taylor's plaintive melody and words. The brilliance is not in a huge transformation of tone but, rather, in moving the key of the chorus up a major third so that it sounds suddenly burst with harmonic magic, even though McGarry is just singing against a simple A major chord. Hollenbeck recreates the strumming of guitar with various pulses, but he also uses a trombone as a critical contrasting voice, a balance against McGarry's lovely, reedy alto-ish soprano.

Another song that probably couldn't stand too-too much transformation is the Bee Gees' "How Deep Is Your Love". Hollenbeck's inner drummer sets up a skittering double-time pattern for the trap kit and the bass, bringing in the Gibbs' melody at what seems like half-time, first on piano and then with McGarry's vocal. The form and harmonies seem largely intact, both on the verse, then on the chorus where Bleckmann joins in vocal harmony. As if to toy with us, then, the arrangement changes its rhythmic approach for a second verse featuring Bleckman. It's a loping, simple-as-pie four-four leading into a wild, Coltrane-ish section that grooves with Gary Versace organ swells and punches under a tenor saxophone improvisation.

Hollenbeck also excels at more complete transformations. The Beach Boys' "God Only Knows" was already one of the most sophisticated songs in the rock canon. This new arrangement takes the brilliant DNA of Brian Wilson's song and pulls it apart, strand by strand or section by section. Hollenbeck uses those fragments to create a new thing that is magical in its new way. He takes a single great line ("God only knows what I'd do without you", for example) and worries it, repeats it, shifts it about harmonically, trades it back and forth between singers and guitar. Then, he does the same thing with another one ("I may not always love you"). To write about it in detail would strain the form of an "album review", but you have to trust me—it is the kind of dazzle that we associate with the very best jazz improvisation or the very best classical composition, all done with the wit and playfulness of a stand-up comedian on a roll.

I probably wouldn't have chosen "Pure Imagination" from Charlie and the Chocolate Factory, and I have a feeling it wasn't Hollenbeck's top choice either, as he leaves so much of the song on the cutting room floor. But what he does use is stretched out across a seamless tone poem, like crumbs dropped by Hansel and Gretel on the path of a long, languorous walk. Lines of melody and lyrics are threaded as jewels onto an act of musical " imagination"—more than ten minutes long and mainly quite gentle but somehow continuously engaging. Though there is virtually no "jazz improvisation" in this performance, Hollenback uses jazz propulsion throughout, even when the mood is contemplative or slow.

The most "jazz" arrangement is for Peter Gabriel's "Don't Give Up", which starts with a trumpet solo over tuba-driven funk and horn blasts. McGarry and Bleckmann sing the familiar melody over a gentler accompaniment in waltz time, but the coda builds on a nine-note pattern (the song's title sung three times in a quick-resolving motif) that grooves on a jazzy 8/8 feel that allows the horns to improvise collectively. Does it all work its way back to the opening funk and horn punctuations? Sure it does. You're dealing here with a very savvy composer.

There is one tune here written wholly by Hollenback. "Kindness" is a setting for a poem by Naomi Nye and sung largely by McGarry. The melody is fresh and somewhat abstract, but it features several harmonic climaxes that act as hooks for the listener. You could almost say that he similarly has his way with the folk tune "Down to the River to Pray" because the source material is so simple and still. This performance opens the recording on a somber and chilling note, but one that shows off so much of what makes this artist so special. Hollenbeck is a master of the timbral colors that he has to work with, so this simple tune seems to go from ochre to grey-blue, from a chilly lavender to reds and bright cobalts. His high and light instruments work in chattering patterns without sounding silly, instead creating swirls of rhythm and harmony up high in the arrangement. Remarkably, the vocalists anchor the tune more than any bass line could, opening up all the options for orchestral play.

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