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"I was intimidated by this gig," the local music star said once on stage, "but then I saw a bunch of grown men – probably including some CEOs – falling all over each other to get their picture taken with Chewbacca."

Of course, Messersmith wasn't making fun of the nerdy shenanigans, but rather wholeheartedly joining in. He made a surprise appearance toward the end of the orchestra's performance, which included everything from Henry Mancini's "Pink Panther Theme" to Strauss' "Thus Spake Zarathustra" (from "2001: A Space Odyssey") to the John Williams canon. Between Williams' "E.T." and "Star Wars" themes, a skinny and sharply dressed man in a Darth Vader mask walked with a Stormtrooper escort down the aisle toward the stage, where he was demasked by conductor Obi-Won Vanska. Yep, it was Messersmith, making a grand entrance that his 6-year-old self would have dreamed up.

"This is a song about my first love," he said as he launched into his "Star Wars"-related original song "Tatooine" alongside the orchestra.

Messersmith's invaluable producer/arranger/keyboardist Andy Thompson -- who also helped steer Dessa's mind-blowing orchestra gigs last year -- had his work cut out for him adapting the formerly acoustic "Tatooine" to full orchestration. However, the arrangements in the similarly sci-fi-themed closing song "Once You Get to Know Us" are already laid out nicely on Messersmith's new album, "Late Stage Capitalism." Both songs proved a good fit with the orchestra's dramatic power. Conversely, Messersmith also sounded like a natural as he also performed "Moon River" with the whole crew.

"My strategy in my career has always been to play with musicians on stage who are better than me," he said between songs, "and tonight is the pinnacle of that."

After an intermission -- during which the ball patrons were treated to fancy finger foods and movie-themed cocktails like "7 & 7 Year Itch" -- Messersmith came back out with his own band for a 10-song set. With regular collaborators the Laurel Strings Quartet also in tow, the performance optimized the hall's warm acoustics with lush, gushing versions of the new would-be hit "Monday, You're Not So Bad" and older favorites "It's Only Dancing," "Ghost" and "A Girl, a Boy and a Graveyard."

Even after several songs about death, the mood turned ridiculously playful again at show's end, as Messersmith coached the crowd through a three-part, "Row, Row, Row Your Boat"-like singalong version of "Violet." Then he encored with a truly unplugged, ukulele-plucked take on "Everybody Gets a Kitten," which again had the regally dressed audience joyously singing like a bunch of kindergarteners. Who knew going to Orchestra Hall could make you feel so much like a kid again?