Penniman portraitist, ornamental artist, and draftsman, worked principally in the Boston, Massachusetts area and in Baltimore, Maryland, during the early nineteenth century. Bornin 1782, he was the son of Elias Penniman and Anna Jenks of Milford, Massachusetts. At about age eleven, he apprenticed as a decorative painter, since his earliestknown signed work is a painted clock dial dated 1793. At this time, he experimented with easel painting, executing a self-portrait in miniature, a scene depicting afamily group dated 1798, and a landscape of Meeting House Hill in Roxbury, Massachusetts, from 1799, among other images.Although Penniman painted portraits throughout most of his career, he principally secured income through his considerable skills in decorative painting. In 1803, heopened a shop on the same street in Roxbury as clockmaker Simon Willard (1753–1848) and across from John Doggett (1780–1857), a looking-glass and framemaker, gilder, and carver. Penniman provided supplementary ornamental services to these men, such as decorating the faces on Willard’s clocks, painting Doggett’sshop sign, and designing cabinetmaker labels.In 1805, he married Susanna (or Susan) Bartlett, with whom he had four children. During this year, he moved his operation to Boston’s South End, where heremained for the next twenty-one years. A member of St. John’s Masonic Lodge, Penniman is credited with decorating the interior of Boston’s Masonic Hall, thenlocated in the Old State House, a collaborative effort with famed architect Alexander Parris (1780–1852). In addition to creating trade cards, advertisements, membership certificates, Masonic ritualpaintings, theatrical backdrops, and book illustrations, Penniman generated designs for Staffordshire earthenware potters,worked for the Pendleton Lithographic Press in Boston, and in 1823 won the competition to design the seal for the city of Boston, an image still in use today. Hisartistic influence extended also to teaching, having had several students within his circle, among them Charles Codman (1800–1842), Nathan Negus (1801–1825),Moses A.Swett (c. 1805–1837), and Alvan Fisher (1792–1863).Plagued with financial difficulties, in 1829 Penniman was committed to South Boston’s House of Industry, a poorhouse. During the early 1830s, he moved to WestBrookfield, where he executed at least seven known compositions of friends and relatives. The watercolor on paper portrait of little Ann Elizabeth Crehore is among hismost pleasing likenesses from this period. Penniman died in 1841 in Baltimore, Maryland, where he had moved a few years earlier to be near his son.