The New "Delineating Pencil"

The New "Delineating Pencil": Silhouettes by William Jennys Fig. 1: William Jennys (1774–1859), family group of eight silhouettes, ca. 1805. White paper mounted on black cloth, the hollow-cut silhouettes each 4-3/4 x 3-3/4 inches and the “hole in the doughnut” inside silhouettes each about 3 x 2-1/2 inches. The three hollow-cut examples are embossed “W. Jennys.”  Private collection.  Using both methods of silhouette cutting, Jennys produced an unusual alternating pattern of white and black images within this family group.
by Michael R. Payne and Suzanne Rudnick Payne

Fig. 1: William Jennys (1774–1859), family group of eight silhouettes, ca. 1805. White paper mounted on black cloth, the hollow-cut silhouettes each 4-3/4 x 3-3/4 inches and the “hole in the doughnut” inside silhouettes each about 3 x 2-1/2 inches. The three hollow-cut examples are embossed “W. Jennys.” Private collection.

Using both methods of silhouette cutting, Jennys produced an unusual alternating pattern of white and black images within this family group.

At a rural auction in Maine during the summer of 1979, a couple purchased an old handmade box containing a family group of eight silhouettes (Fig. 1). Three of the silhouettes were signed by the artist using the embossed stamp “W. Jennys” (Fig. 2).1 These silhouettes, also called shades or profiles, are an exciting example of the versatility of early American folk portrait painters. They are the work of William Jennys (1774–1859), who with his father, Richard (ca. 1734–ca. 1809), travelled for sixteen years as itinerant portrait painters between 1792/3 and 1808.2 Oil on canvas portraits by Richard or William Jennys (Figs. 3–7) are in numerous museum and private collections. Less well known is the fact that in 1805, William, responding to a new technical revolution as well as his own artistic sensibilities, began preparing silhouettes with a most unusual decorative quality. We are not aware of a previously published family group of silhouettes by this artist.

Fig. 2: Embossed signature stamp of William Jennys. Embossing was sometimes used to sign silhouettes at this time.
Fig. 2: Embossed signature stamp of William Jennys. Embossing was sometimes used to sign silhouettes at this time.

The art of Richard and William Jennys is the story of the beginning of portrait painting in America. Richard was born in London, England,3 and was one of the earliest artists to be trained and to pursue a painting career in colonial America. His mother and father, also named Richard, immigrated by 1741/2 with their son to Boston, where his father prominently advertised over many years as a notary “From London…by Royal Authority duly admitted and sworn,” offering to write any type of legal document and as an insurer of ships and cargo. It appears that the family was quite wealthy, as a small portion of a relative’s English estate in 1765 imhttp://www.antiquesandfineart.com/articles/mediately provided the Jennys with 200 pounds, followed later by 400 pounds, both significant sums at this time.4

The first reference to Richard in America was when he was admitted to Boston Latin School in 1744. Since students usually entered the school at age 10, he was probably born in 1734. It is not known where Richard received his art education, but there were several artists in Boston with whom he could have apprenticed. By 1764, he was a practicing artist, as Paul Revere sold him a gold frame for a miniature. He painted portraits that he then engraved as mezzotints, including one of prominent clergyman Reverend Jonathan Mayhew in 1765/6. When the Reverend died, Paul Revere engraved a crude replica of Richard’s mezzotint and also offered it for sale.

Fig. 3: Richard Jennys (ca. 1734–ca. 1809), Man with Five Buttons, ca. 1795. Oil on canvas, 30 x 25 inches. Private collection.
Fig. 4: William Jennys (1774–1859), Woman in a Blue Dress, ca. 1800. Oil on canvas, 30 x 25 inches. Private collection.
Fig. 3: Richard Jennys (ca. 1734–ca. 1809), Man with Five Buttons, ca. 1795. Oil on canvas, 30 x 25 inches. Private collection.

Fig. 4: William Jennys (1774–1859), Woman in a Blue Dress, ca. 1800. Oil on canvas, 30 x 25 inches. Private collection.

By 1768, Richard was described as a dry goods merchant, rather than an artist, in both a bond associated with his father’s estate and in a Boston News-Letter advertisement. On July 25, 1770, he married Sarah Ireland, also of Boston. The marriage produced five children, four boys and a girl, with their second son, William, born in January 1774. Richard appears to have returned to his painting profession by the spring of 1776, when he advertised as a painter of portraits along with offering his dry goods for sale. In December 1776, he may have been the “Richard Jennis,” as the name was occasionally written, who joined Lieutenant Woolcut’s Boston militia formed to reinforce the Continental Army at New York.5

Richard departed Boston by the fall of 1783, when his landlady sought to evict him for failure to pay the rent. On October 4 of that year he arrived by ship in Charleston, South Carolina, and for the next nine years painted there and in cities such as Savannah and even the West Indies. He first advertised that he did “Portrait painting in all its various branches” and soon thereafter described himself as a portrait painter “Chiefly in Miniatures.” Sometime after 1787, Richard and his wife, Sarah, apparently divorced. This was not a prosperous time for Richard, as the Savannah newspaper listed him as defaulting on his taxes in 1788, 1790, and 1791.

Fig. 5: Richard Jennys (ca. 1734– ca. 1809) or William Jennys (1774–1859), Young Girl Holding a Book by Pope, ca. 1800. Oil on canvas, 20 x 16 inches. Private collection.  Jennys portraits of children were usually painted on a smaller canvas.
Fig. 5: Richard Jennys (ca. 1734– ca. 1809) or William Jennys (1774–1859), Young Girl Holding a Book by Pope, ca. 1800. Oil on canvas, 20 x 16 inches. Private collection.

Jennys portraits of children were usually painted on a smaller canvas.

Returning to New England, Richard advertised in the New Haven Connecticut Journal on November 20, 1792, that he painted “Portrait Pictures in large and in Miniatures…Also Chaise and other Painting done in the Neatest Manner” and that “He intends opening a School for the Purpose of instructing young Ladies and Gentleman in the Art of Drawing and Painting Flowers, Birds, Landscapes or Portraits.” At this time, Richard, then fifty-eight years old, and his son William, just nineteen, embarked on their sixteen year itinerancy. William’s first known advertisement as a portrait painter was in the April 1793 issues of the Norwich Packet and The Weekly Register of Connecticut (Fig. 8), where he also advertised himself as a drawing and painting instructor.

Richard apparently taught his son the techniques of portrait painting, as they produced remarkably similar portraits in which the direct gaze of the sitter fully engages the viewer. The portraits were a continuation of Richard’s earlier mezzotint design with the bust length body turned three-quarters toward the viewer and painted spandrels often surrounding the figure. Many collectors have difficulty distinguishing between the artists, but William’s faces are generally more dramatic and exaggerated with a stronger single light source. Both artists usually painted on a thirty by twenty-five inch canvas, except for their smaller portraits of children (fig. 5), and both used a distinctive canvas composed of twilled threads, which, along with thinly applied paint, produced a characteristic surface texture. Father and son’s ability to depict clothing with an almost tactile feel to the luxuriant fabrics was rarely equaled at this time.

During their itinerancy in search of portrait commissions, Richard and William occasionally traveled separately, but also journeyed together for extended periods. In several instances, they both signed the portraits of a husband and wife and also worked together on different members of the same family. The first seven years of their itinerancy were mainly centered near New Milford, Connecticut, but William was in New York City long enough to be listed as a portrait painter in the 1797/8 directories. At the turn of the century, they painted mostly in western and central Massachusetts, with forays to several towns in Vermont and into New Hampshire, particularly to Hanover. In 1803, Amanda Johnson of Enfield, New Hampshire, wrote in her reminiscences about the time William painted her family in May of that year: “Painter Mr. Jennis. He would paint daily from 11 A.M. to 1 P.M. and then chat—he was chatty—and play with his dog. He offered to paint mother with me in her arms for $10 extra but did not…Jennis painted Mr. Merrill and wife and Uncle John Harris and wife. He was six weeks painting father and mother and boarding in the family.”

Figs. 6a: William Jennys (1774–1859), Captain Nathan Hoyt and His Daughter Anna Hoyt, Newburyport, Massachusetts, ca. 1805. Oil on canvas, 30 x 25 inches each. Private collection.   Six portraits of the Hoyt family, consisting of the parents and four daughters, remained together as a group until recently (The Magazine Antiques [September 1967]: 255).
Figs. 6b: William Jennys (1774–1859), Captain Nathan Hoyt and His Daughter Anna Hoyt, Newburyport, Massachusetts, ca. 1805. Oil on canvas, 30 x 25 inches each. Private collection.   Six portraits of the Hoyt family, consisting of the parents and four daughters, remained together as a group until recently (The Magazine Antiques [September 1967]: 255).
Figs. 6a, b: William Jennys (1774–1859), Captain Nathan Hoyt and His Daughter Anna Hoyt, Newburyport, Massachusetts, ca. 1805. Oil on canvas, 30 x 25 inches each. Private collection.

Six portraits of the Hoyt family, consisting of the parents and four daughters, remained together as a group until recently (The Magazine Antiques [September 1967]: 255).

The five years between 1804 and 1809 were centered in Newburyport, Massachusetts. This was the last phase of their itinerancy, and a period of great change for the pair, both in their personal lives and finances. In October 1804, William made the opportune purchase of property on fashionable High Street in Newburyport for $760. Richard, although he was now about seventy-one years old, continued as a portrait painter, placing five advertisements in the Newburyport Herald in 1805.

Fig. 7: William Jennys (1774–1859), Woman with Double Head Band, ca. 1805. Oil on canvas, 30 x 25 inches. Private collection.  This portrait is unusual as the arm is in front of the spandrel. It was among the few items that noted Connecticut antiques dealer Mary Allis retained until her passing.
Fig. 7: William Jennys (1774–1859), Woman with Double Head Band, ca. 1805. Oil on canvas, 30 x 25 inches. Private collection.

This portrait is unusual as the arm is in front of the spandrel. It was among the few items that noted Connecticut antiques dealer Mary Allis retained until her passing.

It was during this period that William obtained the newly introduced physiognotrace so that he could produce silhouettes. An impressive advertisement appeared at least three times in the Concord Courier of New Hampshire starting in June 1805 (Fig. 9). In the advertisement, William announced his taking of silhouettes during his stay at Mr. George’s tavern. He had already used the instrument in Salem and Newburyport and described “his new invented patent Delineating Pencil: which for accuracy, excels any machine before invented for that purpose. He reduces from the shadow; therefore, the person is not incommoded with any thing passing over his face, nor detained over six minutes.”6

Silhouettes had become increasing popular in America during the last decades of the 1700s and large numbers were produced in the very early 1800s. Much discussed theories of physiognomy by the Swiss minister Johann Kaspar Lavater (1741-1801) in the late eighteenth century suggested that the profiled features of the head revealed a person’s true character.7 This led artists to use a variety of drawing machines to obtain the most accurate profile possible. Such devices also greatly reduced the time and cost to produce these silhouettes. In the mid-1780s, Gilles-Louis Chretien (1754–1811), a musician employed by the French royal court, announced the invention of the physionotrace (written in America as physiognotrace) that produced profiles of incredible accuracy in four minutes. Chretien’s device was about five feet high and two feet wide with tripod legs. The artist stood next to this easel-like device and looked through an eyepiece at the sitter. The eyepiece was attached to a pantograph and as the artist followed the sitter’s profile, the connected arm of the pantograph mechanically drew the image. This apparatus was really not a new invention and at least two Americans were granted patents for similar devices. Additional instruments with further modifications were soon invented and sold. There was even a book published in Boston during 1805 that included directions for making a physiognotrace.8

Fig. 8: Advertisement published in The Weekly Register, Norwich, Connecticut, April 1793.  This is the first advertisement by William Jennys that has been located.
Fig. 9: Advertisement published in the Courier of New Hampshire, Concord, New Hampshire, June 1805.  This is the only advertisement that has been located in which William Jennys noted he produced silhouettes.
Fig. 8: Advertisement published in The Weekly Register, Norwich, Connecticut, April 1793.

This is the first advertisement by William Jennys that has been located.

Fig. 9: Advertisement published in the Courier of New Hampshire, Concord, New Hampshire, June 1805.

This is the only advertisement that has been located in which William Jennys noted he produced silhouettes.

William’s advertisement of the physiognotrace declared to his customers that they would receive the best possible image using the new and highly precise device. Yet, competition meant his prices were low and William offered two images for twenty-five cents. He also sold oval, round, and square frames, as well as a silhouette of Thomas Jefferson.9 While this was the only time William advertised silhouettes (fig. 9), his stay in Concord was also memorable in the matter of love, as he married his innkeeper’s daughter, Mary George, on December 23, 1806.

Fig. 10: William Jennys (1774–1859), hollow-cut silhouette, ca. 1805, also shown in figure 1. White paper mounted on black cloth, 4-3/4 x 3-3/4 inches. Private collection.
Fig. 10: William Jennys (1774–1859), hollow-cut silhouette, ca. 1805, also shown in figure 1. White paper mounted on black cloth, 4-3/4 x 3-3/4 inches. Private collection.

William gave the family group of silhouettes (fig. 1) a most unusual level of visual sophistication. Although there were many variations, silhouettes at this time were usually hollow cut. The artist cut the profile out of the center of a piece of white paper and the white paper was then placed over black paper or cloth.10 This emphasized the outlined features of the face and, according to the ideas of physiognomy, displayed the sitter’s character (Fig. 10). Rarely made during the earliest years of the 1800s were silhouettes in which the outside portion of the white paper was discarded, producing the profile from the inside white image. Sometimes called “hole in the doughnut” inside silhouettes, when mounted on a black background, this produced a distinctly different image of the sitter (Fig. 11).11 Using the same white paper, William produced a combination of hollow-cut and “hole in the doughnut” inside profiles for the different members of the family group. A close examination of the group reveals that the “hole in the doughnut” inside silhouettes were not the center of the hollow-cut examples, but were produced independently. William’s combination of these two styles created an unusual decorative pattern of alternating black and white images when the family group was displayed together.12

In the silhouettes (fig. 1), William’s men have long hair falling down their backs and tied bands around their necks. The older women wear large mob caps pulled up by a ribbon to produce a fluffy top, and the younger woman has hair piled higher at the top of the head and soft curls around her face, all reflecting details of American dress during the 1790s and before 1810.13

Figs. 11a: William Jennys (1774–1859), “hole in the doughnut” inside silhouettes, ca. 1805, also shown in figure 1. White paper mounted on black cloth, each about 3 x 2-1/2 inches. Private collection.
Figs. 11b: William Jennys (1774–1859), “hole in the doughnut” inside silhouettes, ca. 1805, also shown in figure 1. White paper mounted on black cloth, each about 3 x 2-1/2 inches. Private collection.
Figs. 11a, b: William Jennys (1774–1859), “hole in the doughnut” inside silhouettes, ca. 1805, also shown in figure 1. White paper mounted on black cloth, each about 3 x 2-1/2 inches. Private collection.

A search for other silhouettes with the “W. Jennys” embossed signature led us to two unknown men (New Hampshire Historical Society and The Metropolitan Museum of Art, New York), a man backed with an 1806 Walpole, New Hampshire, newspaper (private collection), and a woman offered on eBay in 2008. Silhouettes of John and Grace Bradley are at the New Hampshire Historical Society in Concord, New Hampshire. All of these examples are hollow-cut silhouettes, which had the extra paper needed for the embossed “W. Jennys” signature.

In 1807, three years after he acquired the High Street property, William sold it for $2,250, nearly tripling his investment. During the next two years, he engaged in a flurry of successful land transactions. A legal notice in the Salem Gazette on February 19, 1808, described his purchase of half an estate containing twelve land parcels, primarily in Ipswich. Considering his bill of sale for the portrait of Mr. James Clarkson in 1807 was a mere $25.00 plus $6.50 for the frame, it is not surprising that he increasingly turned his attention to real estate. William’s last known paintings are the wedding portraits of his wife’s brother from May 1808. Richard continued to paint portraits, and the last advertisement we have found was in the Portland Gazette of June 1809 declaring that he would paint “Portrait Pictures, large as life.” He was now about seventy-five years old, and reportedly died in Portland, Maine, shortly thereafter.14

By April 1809, William had sold all his real estate and resided for a short time in Nassau, the Bahamas. He and his wife next moved to New York City, where William was described as a comb maker and later as a florist. The couple had two sons, and Mary apparently died in New York City. In 1817, William moved to Littleton, New Hampshire, where his wife’s parents had settled, and again became involved in real estate transactions. During 1819/20, Mary’s sister, Laura, became his second wife. Eleven years were spent as a farmer and tavern keeper in Coventry, New Hampshire, and toward the end of his life, he was again back in New York City as a florist. He died on October 21, 1859, at age 85 and was buried at Greenwood Cemetery in Brooklyn. Over two hundred years later, the portraits and silhouettes of Richard and William Jennys continue to delight as well as surprise us.


This article is dedicated to Paul and Ada “Stevie” Young who purchased these silhouettes in 1979, and to William Bright Jones who so enjoyed researching Richard and William Jennys—old friends who will never be forgotten.


Michael R. Payne, Ph. D. and Suzanne Rudnick Payne, Ph. D. research early American folk artists and are members of the American Folk Art Society. This is the eighth article they have published on early American painters.


1. 1. George Morrill auction, Maine, August 21, 1979, lot 326.

2. Over the past seventy years, several researchers have added to our knowledge of Richard and William Jennys: Frederick F. Sherman, Agnes M. Dods, William Sawitzky, William Warren, and, in particular, William Bright Jones. This is summarized in William Bright Jones, The Portraits of Richard and William Jennys and the Story of Their Wayfaring Lives, in Painting and Portrait Making in the American Northeast, Peter Benes, editor, Vol. 19 (Boston: Dublin Seminar for New England Folklife, Boston University, 1994), 64–97. To this biography, we add new details about Richard’s birth and death, his father, Mary Jennys, several advertisements, the silhouettes, etc.

3. Based on the earliest recorded date (1741/2) of his father in Boston and www.groserfamilies.com.

4. Nicholas Coxe of Middlesex, England, an uncle of Richard’s father, provided bequests to various family members including “Richard Jennys of Boston in New England and Richard Jennys, his son.” See Henry F. Waters, Genealogical Gleanings in England, Vol. 69 (Boston: New England Historical and Genealogical Register, 1895), 513.

5. William H. Whitmore, A Report to the Record Commissioners, Vol. 25 (Boston: Rockwell and Churchill, 1894), 20–21.

6. The unusual description “patent Delineating Pencil” suggests that William may have purchased an instrument or franchise from William King. King was a silhouette artist who also made and sold instruments and used this phrase in his advertisements. See Peter Benes, Machine-Assisted Portrait and Profile Imaging in New England after 1803, in Painting and Portrait Making in the American Northeast, Peter Benes, editor, Vol. 19 (Boston: Dublin Seminar for New England Folklife, Boston University, 1994), 138–150.

7. For a history of physiognomy and the physiognotrace see Ellen G. Miles, Saint-Memin and the Neoclassical Profile Portrait in America, (Washington: National Portrait Gallery and the Smithsonian Institution Press, 1994). Physiognomy should not be confused with the later phrenology movement.

8. Benes, Painting and Portrait Making.

9. A major part of the profit may have been the sale of the frames. Frames were available from between fifty cents to as much as four dollars according to advertisements by other silhouette artists.

10. Cut and pasted silhouettes using black paper which were then mounted on lithographs or painted backgrounds became popular during the 1830s.

11. Alice Van Leer Carrick, Shades of our Ancestors American Profiles and Profilists, (Boston: Little, Brown, and Co, 1928), 8.

12. The family group of eight silhouettes (fig. 1) descended in the Bradley-Burrows families and, when discovered at the auction, were found with a fully painted profile labeled on the back “S. A. Bradley” (by a different artist). The silhouettes may be members of S. A. Bradley’s family, as they coincide with the age and gender of the other Bradley family members living in their Concord, New Hampshire home. See Nathaniel Bouton, The History of Concord (Concord, New Hampshire: Bennig W. Sanborn, 1856), 634–636.

13. Blume J. Rifken, Silhouettes in America, 1790–1840 A Collector’s Guide, (Burlington, Vermont: Paradigm Press, 1987), 12–13.

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