Youngest entrant wins Mr. Healdsburg contest with original rap song

Stories of a magical pond, smooth rap licks and resplendent headwear helped propel a 26-year-old mechanical engineer to the title of Saturday night at the Raven Theater.

Carried by a palpable self-confidence that stood out even among eight contestants who rarely showed signs of inhibition, by a combination of audience votes and those from a five-person panel of judges.

The eighth annual Mr. Healdsburg beauty pageant featured eight contestants and a raucous crowd of mostly women (about 400 people attended the event, according to event organizer Carol Noack). Contestants were judged on a talent portion, a beachwear modeling exhibition and a question-and-answer session.

Sekhon – whose contest name, “Mr. Token,” referred to being of Indian heritage in a town of mostly white inhabitants – wore a blue jumpsuit and a Native American headdress during the contest’s talent portion, for which Sekhon performed a rap spmg about Healdsburg.

The song ended with: “Vote for the champ, the brute, the player / because after this is over, I’m coming for the mayor.”

For the swimsuit modeling portion of the contest, Sekhon kept the headdress on but swapped out his one piece garment for a life vest and some leopard-spotted swim shorts. In the final portion of the contest, the question-and-answer segment, Sekhon emerged in a hulking fur coat and told of a Pomo Indian legend that there is a magical pond somewhere near the town Plaza, though he didn’t know precisely where.

Other contestants also brought notable acts. Matt Paille (Mr. Epicurean) did an elaborate cooking demonstration where he prepared plates of chicken marsala for the judges and used his samurai sword to open a champagne bottle.

Michael Laird (Mr. Magic) pulled a table cloth out from under a lunch set-up without knocking anything over; Scott Keneally (Mr. Tall Tales) recounted an embarrassing story involving a sleepover; and Cooper Conrad (Mr. Decoy) performed a juggling act on stilts – at one point appearing to almost tip over before regaining his balance.

“Good save,” said the show’s Master of Ceremonies, Samantha Vega.

Conrad also made some interesting comments during the show’s question-and -answer portion. Responding to a question about a past mistake, he recounted totaling his mother’s car as a teenager and blaming the crash on a hostile insect. Later, Conrad referenced Jimmy Carter as part of a comment about Healdsburg’s benevolence.

Between ticket sales, food sales and donations, the sold-out pageant brought in over $14,000 for the which event organizer Carol Noack said was the most money the annual event has ever yielded.

“It is especially good because the arts are hard to fund these days,” Noack said.

For winning the contest, Sekhon received a gift certificate to coffee shop and will be able to design and name his own pizza at shop in Healdsburg. Sekhon was the youngest of the contest’s eight entrants, Noack said.

Among those attending Saturday’s event was last year’s contest winner, , who wore his white “Mr. Healdsburg” sash for what was likely the last time. Bairdsmith said he had been honored to hold the title but was ready to pass it on to a new winner.

“It’s been an honor and a burden, so I’m thrilled to pass it on,” Bairdsmith said. “I don’t need that much attention from women. It sounds good, but it’s not – just ask Brad Pitt.”