Warning: I’m going to talk about classical music but it’s only going to be a little boring, I promise.

There are lots of different ways for rock star kids to rebel against their rock star parents. If you’re Hank Williams III, you rebel against two generations of country music establishment by playing nasty-ass punk rock. If you’re Jakob Dylan and your dad is a living legend, you rebel by sucking. If your parents are dyed-in-the-wool folkies like Kate McGarrigle and Loudon Wainwright III, you rebel by composing a lavish orchestral piece that calls for three flutes, three oboes, a piccaolo, an English horn, four clarinets, two bassoons, two trumpets, two trombones, two bass trombones, a tuba, a celesta, glockenspiel, various percussion and a whole host of strings. Maybe his parents could get by with nothing more than an acoustic guitar, but Rufus Wainwright likes to think big.

Oh, almost forgot, there’s also a contrabassoon.

Last year, the San Francisco Symphony commissioned the New York native to compose a piece for them setting a handful of Shakespearean sonnets to music. Wainwright was jumped at the opportunity because, as he writes in the program notes, “One cannot immerse himself/herself in Shakespeare’s sonnets and not be submerged, drowned and finally resurrected a better human being. They are, hands down, the greatest works ever written.” Wainwright’s enthusiasm for the source material shone though in both the composition and his vocal performance.

While a major symphony asking a pop star to compose a classical piece for them may seem a little odd, in Wainwright’s case it makes a lot of sense. Since releasing his eponymous debut album in 1998, Wainwright’s music has always has always had a lavish orchestral bent, which has only gotten more pronounced over time. In 2008, he even went as far as composing a French-language opera, Prima Donna, that premiered the next year as part of the Manchester International Festival. Of all the pop stars to take on this assignment, Wainwright is probably the most natural fit.

Even so, there’s more than a hint of novelty to the pairing, which is why in an evening that saw it sandwiched between two other pieces, Five Shakespeare Sonnets was clearly the main attraction. Immediately preceding the first piece, Darius Milhaud’s La Creation du Monde, conductor Michael Francis told the audience apologetically, “Rufus won’t be long, we’re just going to do this one first.” I know it was a “give the people what they want” type of gesture, but it really undersold what I thought was the strongest part of the show. Written by the French composer in 1923, La Creation du Monde, is a poppy, jazz-inflected piece that’s an inspired choice to hook all the people who were there just to see the guy who wrote “Cigarettes and Chocolate Milk.” Milhaud composed the piece immediately following his first trip to the United States where he had become absolutely drunk on jazz. The rhythms swing giddily and arrangements turn on a dime. It’s a kid-in-a-candy store type of composition where Milhaud seems delighted to display every the trick he just learned obsessively studying jazz bands in the States. You can hear the a lot of the hybrid jazz/classical music later popularized by George Gershwin (who released the strikingly similar Rhapsody in Blue the next year), Leonard Bernstein and Dave Brubeck (who actually studied under Milhaud at Mills College in Oakland) loud and clear. The main melody that runs through the piece actually sounds nearly identical to the theme that Nino Rota wrote for The Godfather in the early 70s, just transposed to a major key.

After Le Creation du Monde finished, the number of musicians onstage nearly doubled for Five Shakespeare Sonnets. Wainwright came out last wearing a puffy white shirt, purple slacks and shiny black shoes. He looked, appropriately, like someone about to step onstage as Lysander in a summer stock production of Midsummer Night’s Dream. Granted, he was showing an awful lot of chest hair for someone standing onstage at a symphony hall.

As soon as Wainwright opened his mouth, any doubts about the whole endeavor immediately got tossed out the window. Homeboy can sing. Wainwright’s tenor soars but he retains a certain mush-mouth quality (especially on his consonants) that gives everything he sings a particularly distinctive character. He may have spent a year writing string arrangements, but his voice is still clearly the star. He has a very particular melodic sensibility and is effortlessly able to fit the Shakespearean verse into it with minimal difficulty, rarely seeming awkward or forced.

For the first three sonnets (numbers 43, 20 and 10) his arrangements were generally unobtrusive, mostly sinking into the scenery, providing a bed for the vocals to take center stage with the celesta as the lead instrument — although when it got loud, as it occasionally did, the volume came from a swell of strings and horns. It was in the penultimate sonnet where things really got interesting. No. 129 featured a dark, driving string figure charging ahead though a playful, yet dissonant, vocal melody. The concluding sonnet was was No. 87, which started off as an intimate confessional only to unexpectedly explode into a lushly dramatic crescendo of strings only to be, just as unexpectedly, interrupted with a mammoth stab of dissonance from the horns and dropped right back into the quiet remorseful place where it started.

The third piece of the evening was Kurt Weill’s Second Symphony, which fit in with the first two thematically more so than sonically. Weill’s image as Weimar Germany-era rabble rouser, and Bertolt Brecht’s partner in crime, makes sense when paired with a work of someone like Wainwright who largely exists outside of the classical music establishment. Although, given the success of Five Shakespeare Sonnets, I’m not sure how long Wainwright is going to be considered a tourist in this world and not just an inhabitant that also like to write pop songs.

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