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10 Weirdest Pieces of Art from Oprah's Auction

Oprah at her auction.
Oprah at her auction.
Photo: Jennifer Swann

Oprah Winfrey got into the spring cleaning spirit a little late (or early?) this year and invited the public to come peruse her old junk on Saturday at the Santa Barbara Polo & Racquet Club. With $10 valet parking, a fleet of food trucks that included the Santa Barbara-based Georgia's Smokehouse, $50 auction catalogs for sale, an outdoor bar area with $8 Bloody Mary's, a full camera crew taping the auction for Oprah's Own network, and portable potties that were nicer than most indoor toilets, the benefit for Oprah's Leadership Academy in South Africa felt more like a fantastical fundraising gala than a bargain yard sale.

The Montecito-based media mogul showed up around 10 a.m. in a neon yellow blouse and jeans and played up to the Santa Barbara crowd, hailing the beach town as one of her favorite things and then repeatedly singing the words "Santa Barbara!" and reminding everyone to "think of the children" in South Africa when placing their bids for items like her old burnt-orange armchair with gold fringe tassels or the stair master she used to work out on with personal trainer Bob Greene. "Remember there's no friends at an auction," she cautioned, taking bids from her own BFF Gayle King and name-dropping Tyler Perry, whom she says was envious of her art collection.

From naively-painted folk art to various portraits of Oprah, surely the strangest items up for auction were the pieces of inexplicable artwork she's amassed over the years. We documented ten of the weirdest paintings, drawings and collages that we saw at the Oprah auction, although sadly, our bids just weren't competitive enough to take any of them home.

"The Makeover" by Chris Roberts-Antieau
"The Makeover" by Chris Roberts-Antieau
Photo: Jennifer Swann

10. "The Makeover," by New Orleans artist Chris Roberts-Antieau.

Maybe it's a folksy homage to the myriad makeovers Oprah's facilitated on her talk show over the years?

Kaminski Auctions handlers displaying a collage by Phoebe Beasley
Kaminski Auctions handlers displaying a collage by Phoebe Beasley
Photo: Jennifer Swann

9. "The Women of Brewster Place," by Phoebe Beasley

Bidding started at $1,600 and closed at around $4,500 for this hand-drawn collage inspired by "The Women of Brewster Place," a 1989 TV mini series Oprah starred in. Oprah is pictured at center, "looking exactly like my grandmother," she says.

Painting of Oprah with two dogs on her lap.
Painting of Oprah with two dogs on her lap.
Photo: Jennifer Swann

8. Portrait of Oprah with two dogs on her lap

Judging by Oprah's hairdo, the painting looks like it might've been made around 2003.

 

Kaminski Auctions handlers displaying a piece called "Ladies' Day."
Kaminski Auctions handlers displaying a piece called "Ladies' Day."
Photo: Jennifer Swann

7. "Ladies' Day" Collage

Bidding started at $2,250 for this collage Oprah says is all about church ladies dressed up in fancy hats for church on Sunday.

Painting from Oprah's collection
Painting from Oprah's collection
Photo: Jennifer Swann

6. This painting of an unidentified Victorian woman with a protruding chin

It doesn't seem to fit in with Oprah's broader collection of African American folk art, does it?

Painting from Oprah's collection
Painting from Oprah's collection
Photo: Jennifer Swann

5. This curious painting of a girl about to stick her finger into a watermelon

Oprah says she's been "a collector of folk art for a very long time and then my home here just didn't fit the folk."

 

Painting by Cynthia Janet White
Painting by Cynthia Janet White
Photo: Jennifer Swann

4. This 1992 painting by L.A. artist Cynthia Janet White

The subjects mostly have theirs backs to the viewer -- but are they giving us the thumbs up sign?

Drawing of Oprah Winfrey
Drawing of Oprah Winfrey
Photo: Jennifer Swann

3. This pencil drawing of Oprah

It seems to have been made around 1994 judging by the hairdo, which resembles Jennifer Aniston's "Rachel" cut.

Oprah drawing by M. Herman
Oprah drawing by M. Herman
Photo: Jennifer Swann

2. This pastel-colored portrait of Oprah

The hair, once again, is the focus of the image. We'd be willing to wager that this iconic hairstyle and pink turtleneck look dates back to the late 1980s.

 

Painting by Pierre Joseph Valcin
Painting by Pierre Joseph Valcin
Photo: Jennifer Swann

1. And finally, this painting by Haitian artist Pierre Joseph Valcin

At first it seems like a child-like painting of a woman gathering corn, but then we notice she's actually urinating in the field. Who wouldn't want to mount this painting in their, uh, bathroom?


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