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William R. Hollingsworth Sold at Auction Prices

Painter, b. 1910 - d. 1944

From losing his mother as a child to a forced move back to Mississippi after graduation from the Chicago Institute of Art, the influences in artist Hollingsworth’s life gave a uniquely sensitive perspective to his oil and watercolor paintings, especially his best-known works depicting African-American culture in Mississippi during the early 20th century. Painter William R. Hollingsworth, Jr. is considered a Southern treasure, an artist who used both light and sadness to depict the way of life around him.

Celebrated during his lifetime, painter William Hollingsworth collected prizes from the National Watercolor Society, Chicago Arts Club, and Southern States Art League, and he founded the Art Department at Millsaps College. His widow established an art scholarship endowment in Hollingsworth’s name at his alma mater, the University of Mississippi. The Mississippi Museum of Art displays almost 300 William R. Hollingsworth, Jr. paintings. Collectors can find an abundance of Southern-themed watercolor paintings for sale at online auction.  

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    • WILLIAM R. HOLLINGSWORTH, JR AMERICAN 1910-1944
      Nov. 12, 2022

      WILLIAM R. HOLLINGSWORTH, JR AMERICAN 1910-1944

      Est: $3,000 - $5,000

      A Heated Discussion, watercolor, 14 x 11 in (35.6 x 27.9 cm), framed 21 1/2 x 17 1/2 in (54.6 x 44.5 cm), signed lower right, dated 1943

      Trinity International Auctions & Appraisals, LLC
    • William R. Hollingsworth, Jr., (American/Mississippi, 1910-1944), "Two Girls and a Boy", 1941, watercolor on paper, 9-1/2" x 8", fra...
      Apr. 24, 2022

      William R. Hollingsworth, Jr., (American/Mississippi, 1910-1944), "Two Girls and a Boy", 1941, watercolor on paper, 9-1/2" x 8", fra...

      Est: $1,000 - $1,500

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944) "Two Girls and a Boy", 1941 watercolor on paper signed lower right, titled lower center on board, localized and dated "Jackson '41" en verso. Matted, glazed and framed. 9-1/2" x 8", framed 18-1/2" x 12-3/4"

      New Orleans Auction Galleries
    • William R. Hollingsworth, Jr. (American/MS.)
      Nov. 20, 2021

      William R. Hollingsworth, Jr. (American/MS.)

      Est: $1,500 - $2,500

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944) , "Conversation", 1930, oil on canvas, signed and dated lower left, handwritten label with artist, title and date en verso, 18 in. x 22 1/4 in., framed Provenance: Private Collection, MS; thence by descent.

      Neal Auction Company
    • Attributed to William R. Hollingsworth, Jr.
      Feb. 07, 2021

      Attributed to William R. Hollingsworth, Jr.

      Est: $400 - $600

      Attributed to William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944) , "Birdhouse", oil on board, unsigned, 10 in. x 8 in., framed

      Neal Auction Company
    • William R. Hollingsworth, Jr. (American/MS.)
      Nov. 20, 2020

      William R. Hollingsworth, Jr. (American/MS.)

      Est: $3,000 - $5,000

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944) , "Widow Man", watercolor on paper, signed lower right, partial label and handwritten label with artist and title on backing paper, 11 in. x 17 in., framed . Provenance: Collection of Michael Wilkinson, New Orleans, LA

      Neal Auction Company
    • Attributed to William R. Hollingsworth, Jr.
      Sep. 13, 2020

      Attributed to William R. Hollingsworth, Jr.

      Est: $800 - $1,200

      Attributed to William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944), "Birdhouse", oil on board, unsigned, 10 in. x 8 in., framed

      Neal Auction Company
    • William R. Hollingsworth, Jr. (American)
      Sep. 13, 2020

      William R. Hollingsworth, Jr. (American)

      Est: $1,000 - $1,500

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944), "Figural Studies", graphite and charcoal on paper, unsigned, 19 in. x 23 in., framed . Provenance: Reputedly in the artist's widow's collection; Brown's Fine Art & Framing, Jackson, MS, c. 2003

      Neal Auction Company
    • Attributed to William R. Hollingsworth, Jr.
      Feb. 08, 2020

      Attributed to William R. Hollingsworth, Jr.

      Est: $1,200 - $1,800

      Attributed to William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944) , "Figural Studies", graphite and charcoal on paper, unsigned, 19 in. x 23 in., framed

      Neal Auction Company
    • Attributed to William R. Hollingsworth, Jr.
      Feb. 08, 2020

      Attributed to William R. Hollingsworth, Jr.

      Est: $1,200 - $1,800

      Attributed to William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944) , "Birdhouse", oil on board, unsigned, 10 in. x 8 in., framed

      Neal Auction Company
    • William R. Hollingsworth, Jr. (American/MS)
      Feb. 08, 2020

      William R. Hollingsworth, Jr. (American/MS)

      Est: $3,000 - $5,000

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944) , "Rabbit, Rabbit!", 1943, watercolor on paper, signed and dated lower right, handwritten label with artist, title and date on backing paper, 10 15/16 in. x 16 in., framed

      Neal Auction Company
    • William R. Hollingsworth, Jr. (American/MS)
      Apr. 13, 2019

      William R. Hollingsworth, Jr. (American/MS)

      Est: $3,000 - $5,000

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944), "Untitled: Two Figures", 1939, pen and ink on paper, pencil-signed and dated upper right, ink-signed and dated lower left, inscribed on backing board, 14 1/4 in. x 11 1/2 in., framed. Provenance: Natchez Art Association. Note: “William Robert 'Hollie' Hollingsworth Jr. was one of Mississippi’s most productive artists of the 1930s and 1940s. His ability to capture the regional landscape and people of Mississippi in his sketches, oil paintings, and watercolors led him to be known as the Faulkner of Visual Arts.” Hollingsworth was born in 1910 in Jackson, Mississippi. He studied at the University of Mississippi for two years before attending The School of the Art Institute of Chicago where he graduated in 1934. Unable to find work in Chicago, Hollingsworth returned to Jackson where his wife supported the family while Hollingsworth pursued a full-time career as an artist focusing particularly on race relations and life in Jackson. The ink drawing offered here is an example of his detailed, thoughtful work and characteristic subject matter. Ref.: Arrington, Linda. “William Hollingsworth.” Mississippi Encyclopedia. Apr. 14, 2018. http://mississippiencyclopedia.org/entries/william-hollingsworth. Accessed Mar. 9, 2019.

      Neal Auction Company
    • William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944), "The Shadow of the Law"
      Jul. 29, 2018

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944), "The Shadow of the Law"

      Est: $3,000 - $5,000

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944) "The Shadow of the Law", 1943 watercolor on paper signed upper left and lower right, signed, titled and dated en verso, "Eugene O'Karma, Atlanta, GA" label with title en verso. Framed. 11-1/4" x 15-1/2", framed 17" x 21"

      New Orleans Auction Galleries
    • William R. Hollingsworth, Jr., (American/Mississippi, 1910-1944), "Still Life with a Basket, Lemons and a Bottle of Wine" "Still Lif...
      Jan. 28, 2018

      William R. Hollingsworth, Jr., (American/Mississippi, 1910-1944), "Still Life with a Basket, Lemons and a Bottle of Wine" "Still Lif...

      Est: $600 - $900

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944) "Still Life with a Basket, Lemons and a Bottle of Wine" "Still Life with a Pottery Jug and a Bowl of Lemons" two watercolors on paper both signed lower right, former dated "1942". Both matted, glazed and framed. sights: former 7-1/4" x 9", latter 4-3/4" x 6-1/8"

      New Orleans Auction Galleries
    • William R. Hollingsworth, Jr., (American/Mississippi, 1910-1944), "Gossip", 1940, watercolor on paper, sight 13" x 19"
      Apr. 22, 2017

      William R. Hollingsworth, Jr., (American/Mississippi, 1910-1944), "Gossip", 1940, watercolor on paper, sight 13" x 19"

      Est: $3,000 - $5,000

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944) "Gossip", 1940 watercolor on paper signed and dated lower right. Matted, glazed and framed. sight 13" x 19"

      New Orleans Auction Galleries
    • William R. Hollingsworth, Jr., (American/Mississippi, 1910-1944), "Still Life with a Basket, Lemons and a Bottle of Wine" and "Still...
      Apr. 22, 2017

      William R. Hollingsworth, Jr., (American/Mississippi, 1910-1944), "Still Life with a Basket, Lemons and a Bottle of Wine" and "Still...

      Est: $1,000 - $1,500

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944) "Still Life with a Basket, Lemons and a Bottle of Wine" and "Still Life with Pottery Jug and a Bowl of Lemons" two watercolors on paper both signed lower right, former dated "1942". Both matted, glazed and framed. sight: former 7-1/4" x 9", latter 4-3/4" x 6-1/8"

      New Orleans Auction Galleries
    • W. R. Hollingsworth, Jr. (Mississippi, 1910-1944)
      Mar. 22, 2015

      W. R. Hollingsworth, Jr. (Mississippi, 1910-1944)

      Est: $2,000 - $4,000

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944) "The Pencil Seller", 1940, graphite on paper, signed and dated "2/7/40" lower right, titled lower left, 17" x 14". Unframed.

      New Orleans Auction Galleries
    • William R. Hollingsworth, Jr. (American/MS, 1910)
      Feb. 09, 2014

      William R. Hollingsworth, Jr. (American/MS, 1910)

      Est: $500 - $750

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944), "Portrait of a Man, Jackson, Mississippi", watercolor on paper, signed lower left, 7 in. x 5 1/2 in., period frame Note: William Hollingsworth is best known for his watercolors of African-American life in rural Mississipppi. In 1937, one of his watercolors won the William Tuthill prize in an international watercolor show at the Art Institute of Chicago. This watercolor is an appealing example of his intimate portrait studies, conveying a sense of thoughtfulness.

      Neal Auction Company
    • Wm. R. Hollingsworth, Jr. (U.S./MS, 1910-1944)
      Dec. 08, 2013

      Wm. R. Hollingsworth, Jr. (U.S./MS, 1910-1944)

      Est: $5,000 - $8,000

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944), "Gossip", watercolor on paper, signed and dated lower right "William Hollingsworth, Jr. 1940", sight 13" x 19". Glazed, matted and framed.

      New Orleans Auction Galleries
    • William R. Hollingsworth
      Jul. 13, 2013

      William R. Hollingsworth

      Est: $5,000 - $7,000

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944), "Scrugg's Palace, Old Canton Road", 1943, watercolor on paper, signed and dated lower right, signed, titled, dated and inscribed en verso, 15 3/4 in. x 23 in., framed. Provenance: Descended in the family of noted Mississippi art collector Betsy Irby to the present owner, 2011. Note: "To Paint and Pray: The Art and Life of William Hollingsworth", a major retrospective organized by the Mississippi Museum of Art, is on view at the Ogden Museum of Southern Art, New Orleans, until July 14, 2013.

      Neal Auction Company
    • Wm. R. Hollingsworth, Jr. (U.S./Miss., 1910-1944)
      Apr. 19, 2013

      Wm. R. Hollingsworth, Jr. (U.S./Miss., 1910-1944)

      Est: $5,000 - $8,000

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944), "The Bourbon Street City Slicker", ca. 1943, watercolor on paper, signed lower left, sight 13-1/2" x 9-1/2". Glazed, matted and framed. Provenance: Private collection, New Orleans, Louisiana. A native of Jackson, Mississippi, Hollingsworth attended the School of the Art Institute of Chicago. Originally intending on a career as a commercial artist, he soon realized his sensibilities and talents would be better suited in pursuing the finer arts. Upon returning to his hometown, Hollingsworth found himself drawn to the local black culture, a segment of the Southern population often overlooked by academically trained white artists. He soon dedicated his considerable artistic skills to creating haunting images of the everyday people around him. Hollingsworth was integral to the creation of the Art Department at Millsaps College, where he was an instructor from 1941-1943. In 1944 he was awarded a grant by the Southern States Art League.

      New Orleans Auction Galleries
    • William Robert Hollingsworth, (American, 1910-1944), Portait of a Girl
      Feb. 21, 2013

      William Robert Hollingsworth, (American, 1910-1944), Portait of a Girl

      Est: $400 - $600

      William Robert Hollingsworth (American, 1910-1944) Portait of a Girl oil on canvas signed Wm. Hollingsworth (lower left) 38 x 27 inches.

      Hindman
    • William R. Hollingsworth (American/Mississippi)
      Nov. 18, 2012

      William R. Hollingsworth (American/Mississippi)

      Est: $1,500 - $2,500

      William R. Hollingsworth (American/Mississippi, 1910-1944), "Mississippi Landscape with Train Tracks and Telephone Poles" and "Mississippi Town with Shotgun Houses", 1944, double-sided watercolor on paper, each initialed and dated lower right, 22 in. x 14 in. Provenance: Acquired by a Virginia collector while visiting relatives in Jackson, MS, c. 1944; thence by descent Note: Hollingsworth is best known for his watercolors of the countryside near Jackson and for his depictions of African Americans in their environs. The double-sided work offered here has a view from each of these favored themes, with one side showing a vast landscape with power lines and a train track, and the other side a black man within a group of shotgun houses. In 1937 Hollingsworth won the William Tuthill Prize at an international watercolor show at the Art Institute of Chicago. Unfortunately, his artistic output was limited to a mere tenyears, as the artist took his life in the summer of 1944, the year the watercolors offered here were painted. Starting Bid: $1000

      Neal Auction Company
    • William R. Hollingsworth, Jr., (Mississippi/Chicago; 1910 - 1944), Untitled, Watercolor on paper, 8 3/4" x 13"
      Oct. 27, 2012

      William R. Hollingsworth, Jr., (Mississippi/Chicago; 1910 - 1944), Untitled, Watercolor on paper, 8 3/4" x 13"

      Est: $3,000 - $5,000

      William R. Hollingsworth, Jr. (Mississippi/Chicago; 1910 - 1944) Untitled Watercolor on paper Signed "W. Hollingsworth Jr" LR. A prominent figure in the art scene of Jackson, Mississippi, William Hollingsworth studied at the Art Institute of Chicago. He and his fashion artist wife intended to stay in Chicago, but the Depression forced them to move to Jackson where the couple lived with his father. William worked for the Federal Emergency Relief Administration and later set up a studio in the home. In 1941, he established the Art Department of Millsaps College and taught there for several years. In 1944, he took his life, having become despondent over World War II and his father's ill health. 8 3/4" x 13"

      Ripley Auctions
    • William R. Hollingsworth (American/Mississippi)
      Jun. 30, 2012

      William R. Hollingsworth (American/Mississippi)

      Est: $5,000 - $8,000

      William R. Hollingsworth (American/Mississippi, 1910-1944), "Mississippi Landscape with Train Tracks and Telephone Poles" and "Mississippi Town with Shotgun Houses", 1944, double-sided watercolor on paper, each initialed and dated lower right, 22 in. x 14 in . Provenance: Acquired by a Virginia collector while visiting relatives in Jackson, MS, c. 1944; thence by descent Note: Hollingsworth is best known for his watercolors of the countryside near Jackson and for his depictions f African Americans in their environs. The double-sided work offered here has a view from each of these favored themes, with one side showing a vast andscape with power lines and a train track, and the other side a black man within a group of shotgun houses. In 1937 Hollingsworth won the William Tuthill Prize at an international watercolor show at the Art Institute of Chicago. Unfortunately, his artistic output was limited to a mere ten years, as the artist took his life in the summer of 1944, the year the watercolors offered here were painted. Please Note: Start Price USD $3000

      Neal Auction Company
    • William Hollingsworth, Jr. (American/MS, 1910)
      Nov. 20, 2011

      William Hollingsworth, Jr. (American/MS, 1910)

      Est: $5,000 - $7,000

      William Hollingsworth, Jr. (American/Mississippi, 1910-1944), "Portrait of Isabel", oil on canvas, signed right upper center, 30 in. x 24 in., framed Provenance: Descended in the family of Nancy Currie Robinson, a close friend of the Hollingsworth family. Note: A prolific draughtsman, William Hollingsworth was continuously skitching his family and friends. He painted numerous oil portraits of his family, such as the one of his sister Isabel offered here. Most noted for his watercolors, the artist's oil paintings have a much different feel. Paints in a straight-forward, realistic style, the portrait shows the tenderness Hollingsworth felt for his sister.

      Neal Auction Company
    • William R. Hollingsworth Jr., (American/MS.)
      Nov. 20, 2011

      William R. Hollingsworth Jr., (American/MS.)

      Est: $2,500 - $3,500

      William R. Hollingsworth Jr., (American/Mississippi, 1910-1944), "Portrait of a Man, Jackson, Mississippi", watercolor on paper, signed lower left, 7 in. x 5 1/2 in., in a period giltwood frame Note: William Hollingsworth is best known for his watercolors of the countryside near Jackson, as well as his depictions of African Americans in their environs. In 1937, one of his studies won the William Tuthill prize at an international watercolor show at the Art Institute of Chicago. The work offered here is an attractive example of his intimate portrait studies, conveying a sense of thoughtfulness. An upcoming major retrospective of William Hollingsworth is planned at the Mississippi Museum of Art.

      Neal Auction Company
    • William R. Hollingsworth, Jr. (American, 1910)
      Nov. 19, 2011

      William R. Hollingsworth, Jr. (American, 1910)

      Est: $5,000 - $7,000

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944), "Scrugg's Palace, Old Canton Road", 1943, watercolor on paper, signed and dated "Mar. '43" lower right, signed, titled, dated and inscribed en verso, 15 3/4 in. x 23 in., attractively matted and framed

      Neal Auction Company
    • William R. Hollingsworth, Jr.
      Jun. 25, 2011

      William R. Hollingsworth, Jr.

      Est: $7,000 - $10,000

      William R. Hollingsworth, Jr. (American/Mississippi, 1910-1944), "Frosty Morning", watercolor on paper, monogrammed lower right, titled and inscribed en verso, 22 1/2 in. x 29 3/4 in., matted and framed.

      Neal Auction Company
    • William R Hollingsworth (American/Mississippi,
      Apr. 18, 2009

      William R Hollingsworth (American/Mississippi,

      Est: $5,000 - $7,000

      William R Hollingsworth (American/Mississippi, 1910-1944), "Harvest", charcoal and watercolor on paper, signed and dated "1941" lower right, titled and inscribed "Mrs Lowry" en verso, 14 3/4 in x 18 in., attractively matted and framed

      Neal Auction Company
    • William R. Hollingsworth (American/Mississippi,
      Feb. 07, 2009

      William R. Hollingsworth (American/Mississippi,

      Est: $8,000 - $12,000

      William R. Hollingsworth (American/Mississippi, 1910-1944), "The Wedding", watercolor on paper, signed and dated "'43" lower right, inscribed "William Hollingsworth, Jr., Jackson, Mississippi" en verso, 22 1/2 in. x 30 in., in a period frame * NO RETURNS ARE ACCEPTED ON THE BASIS OF CONDITION * PLEASE READ ALL CONDITIONS OF LISTED WITH THIS ITEM * PAYMENT DUE WITHIN 10 DAYS! * NO PAY PAL * WE DO NOT SHIP ANY ITEMS or ESTIMATE, SEE BELOW SHIPPING POLICY * LOCATED IN NEW ORLEANS, LA *

      Neal Auction Company
    • William R. Hollingsworth (American/Mississippi,
      Jun. 01, 2008

      William R. Hollingsworth (American/Mississippi,

      Est: $700 - $1,000

      William R. Hollingsworth (American/Mississippi, 1910-1944) "Bust Portrait of a Black Youth", watercolor, 10" x 8", signed lower right "Wm R Hollingsworth", accompanied by a letter of authenticity from Mr. Roy Winston Wilkinson of Jackson, Mississippi. Glazed, matted and presented in a contemporary silver gilded frame. Note: William Hollingsworth graduated from the Art Institute of Chicago in 1934 and established the Department of Art at Millsaps College in Jackson, Mississippi, where he taught from 1941-1943.

      New Orleans Auction Galleries
    • William Hollingsworth (American/Mississippi,
      May. 03, 2008

      William Hollingsworth (American/Mississippi,

      Est: $5,000 - $7,000

      William Hollingsworth (American/Mississippi, 1910-1944) , "Fishing", watercolor, signed lower left, Brown's Jackson, Mississippi framing paper en verso, sight 10 3/4 in. x 8 1/4 in * NO RETURNS ARE ACCEPTED ON THE BASIS OF CONDITION * PLEASE READ ALL CON

      Neal Auction Company
    • William R. Hollingsworth, Jr. (American,
      Apr. 13, 2008

      William R. Hollingsworth, Jr. (American,

      Est: $2,000 - $4,000

      William R. Hollingsworth, Jr. (American, Mississippi, 1910-1939) "The Big 'Un", watercolor on paper, 11-1/2" x 14-1/4", pencil titled and signed verso, signed and dated lower right: "Wm. R. Hollingsworth Jr./1939". Glazed and presented in an antique carved oak frame.

      St Charles Gallery
    • William R. Hollingsworth (American-Mississippi, 1910-1944) "Bust Portrait of a Black Youth", watercolor, 10" x 8", signed lower right "Wm R Hollingsworth", accompanied by a letter of authenticity from Mr. Roy Winston Wilkinson of Jackson,
      May. 20, 2007

      William R. Hollingsworth (American-Mississippi, 1910-1944) "Bust Portrait of a Black Youth", watercolor, 10" x 8", signed lower right "Wm R Hollingsworth", accompanied by a letter of authenticity from Mr. Roy Winston Wilkinson of Jackson,

      Est: $1,800 - $2,500

      William R. Hollingsworth (American-Mississippi, 1910-1944) "Bust Portrait of a Black Youth", watercolor, 10" x 8", signed lower right "Wm R Hollingsworth", accompanied by a letter of authenticity from Mr. Roy Winston Wilkinson of Jackson, Mississippi. Glazed, matted and presented in a contemporary silver gilded frame. William Hollingsworth graduated from the Art Institute of Chicago in 1934 and established the Department of Art at Millsaps College in Jackson, Mississippi, where he taught from 1941-1943.

      New Orleans Auction Galleries
    • William Hollingsworth, Jr. (American/Mississippi, 1910-1944), "Rural Cabin Scene", watercolor
      Aug. 02, 2003

      William Hollingsworth, Jr. (American/Mississippi, 1910-1944), "Rural Cabin Scene", watercolor

      Est: $3,000 - $5,000

      signed and dated "1940" lower right, sight 20 in. x 13 1/2 in. SEE PHOTO PAGE 36.

      Neal Auction Company
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