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Hobo Artist

Leanne Castillo, longtime hobo portrait artist and owner of the Hobo Art Gallery in Britt, receives a portrait of her own Friday morning among family, friends and hobos.

BRITT | Applause and cheers filled the crowded Hobo Art Gallery in Britt late Friday morning as a wide grin stretched across the face of Leanne Castillo, the official hobo portrait painter.

Castillo, 85, owner of the Main Avenue North art gallery comprised of dozens of historic hobo oil paintings, was gifted her very own portrait by 2016 Hobo King Ricardo in front of her family, friends and the hobo community.

“What a day,” she said moments after the surprise unveiling of her portrait.

Ricardo, who had been plotting the unveiling for nearly a year, had his longtime friend and pencil artist, Dan Theis, of St. Peter, Minnesota, sketch a portrait of Castillo to thank her for her years of dedication to the hobo community as an artist and friend.

Theis, who attended the surprise unveiling Friday with his wife, Barb, said it was “kind of an honor” to be asked to do such a favor for his friend.

Ricardo said Castillo asked him last year to officially dub her with the hobo moniker, Iowa Shorty, she’s been known by for decades.

“When she asked me to dub her out of all the hobos, I thought, ‘Why me?’” he said. “What do you do? How do you repay her?”

That’s when he remembered Theis, who’s been drawing pencil portraits since his wife was diagnosed with lung cancer four years ago. It took him five hours to draw the portrait of Castillo based on images he obtained from one of her daughters and online. It was completed with a handmade wooden frame.

The final product was a spitting image of Castillo and the smile on her face Friday afternoon. Those in attendance praised Theis’ artistry and carpentry, including Castillo.

Hobo Artist

A pencil-drawn portrait of Leanne Castillo, the official hobo portrait painter from Britt, by Dan Theis, of St. Peter, Minnesota.

“It looks just like me,” she said.

Minneapolis Jewel told Castillo she’d have to find “a special place” in the art gallery for her portrait.

“Thank you, Shorty, for having us and doing such a wonderful job,” Minneapolis Jewel said. “All the hobos appreciate all your work, the time and energy you put in to make us all look so beautiful and a part of history and now you are, too.”

Katherine Ritchie, Castillo’s daughter who lives in Branson, Missouri, attended the event for the first time in a number of years because she knew her mother was going to be honored. Some of her other 11 children were also in attendance.

“Mom’s not extremely emotional, but oh my gosh, she was surprised,” she said.

The unveiling came after Castillo revealed the portrait she painted of 2017 Hobo King Tuck and Queen Minneapolis Jewel, who are the first married couple crowned hobo royalty at the same time in the National Hobo Convention’s 117-year history.

Castillo called it “a momentous year.”

A longtime Britt resident and retired licensed practical nurse, Castillo’s painted nearly 70 portraits of past National Hobo Convention royalty and treasured pieces of local history since 1983.

Hobo Artist

Leanne Castille unveils the portrait of 2017 Hobo King and Queen Tuck and Minneapolis Jewel, respectively, Friday morning at the Hobo Art Gallery in Britt.

Historically, she only paints portraits of each hobo king and queen once, even if they’ve been crowned multiple times, but because the 2017 coronation was a historic milestone, she made an exception this year.

“I painted them how they looked that day,” Castillo said, before revealing the portrait and receiving praise for her work.

The gallery will be open throughout Hobo Days, which runs until Sunday.

Outside of festivities, the gallery will be open Thursdays or by calling 641-843-3250 for an appointment. 

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Reach Reporter Ashley Stewart at 641-421-0533. Follow her on Twitter at GGastewart.



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