Gilbert Stuart (1755-1828), the most successful and resourceful portraitist of America’s early national period, is best remembered today for his many incisive likenesses of George Washington. In the artist’s first retrospective in nearly four decades, The Metropolitan Museum of Art will show nearly 100 works that reveal his talent for capturing both the appearance and the character of his many prominent clients.

Representing all periods of Stuart’s long career and featuring works drawn from private collections and museums in America and Britain, “Gilbert Stuart” opens on October 21.

A highlight of the exhibition will be the display in a single room of 14 of Stuart’s Washington portraits, including the original “Vaughan” likeness, the unfinished “Athenaeum” version and the celebrated “Lansdowne” portrait of 1796, recently acquired by the National Portrait Gallery in Washington, D.C.

The chronological arrangement of the exhibition follows Stuart’s career from its start in his hometown of Newport, R.I., to its end some five decades later in Boston. Within the display, a gallery will be devoted to works painted in each of the seven cities – Newport, New York, London, Dublin, Philadelphia, Washington and Boston – in which the artist practiced his trade and attracted a clientele.

The son of a Scottish émigré who settled near Newport, Stuart demonstrated a precocious artistic talent coupled with an irreverent manner and somewhat rebellious spirit. He honed his skills on a trip to Edinburgh in 1772-73 and a visit to Boston in 1774 and upon his return to Newport, attracted the local elite, many of them business associates of his father.

The first signs of his technical skill are apparent in relatively primitive works fashioned according to the model of contemporary Scottish portraiture, such as the ambitious 1774 double portrait of Francis Malbone and his brother Saunders, painted when the artist was not yet 20. His portrait of his close friend Benjamin Waterhouse from the next year shows vast improvement and this accomplishment led him to seek more training abroad.

In 1777, Stuart traveled to London to seek his fortune. He soon secured a position as an assistant to another American who had relocated to London – the renowned artist Benjamin West (1738-1820), historical painter to King George III. Stuart benefited greatly from this relationship and, with the 1782 exhibition at the Royal Academy of Arts of his boldly original and highly acclaimed full-length portrait “The Skater (William Grant)” the young American became one of the most sought-after painters in Britain.

He was also on good terms with the academy’s president, Sir Joshua Reynolds, who recommended Stuart for many jobs. and the print seller John Boydell, who, in 1785, ordered from Stuart 15 portraits of contemporary artists, six of which will be shown in the exhibition.

After a decade in London, Stuart’s reputation grew along with his debts. To escape his creditors, he moved to the comparatively small city of Dubin. Among his most important works from the period is the 1789 portrait of the newly appointed Lord Chancellor of Ireland, John Fitzgibbon, whose aloof and regal pose Stuart would find useful later in his career.

In 1793, the artist sailed for New York, where he would make the proper connections to gain a sitting with President George Washington. He received numerous commissions, which he completed with great speed and skill, proving himself worthy of painting the leader of the country. Ultimately, through his friend, the diplomat John Jay, whose portrait he also painted, the necessary introductions were made and, assured of sittings with George Washington, Stuart moved to Philadelphia – at that time, the nation’s capitol.

Stuart was granted three sittings with Washington in 1795-96, bringing the skills honed in Britain to bear on his work. In these paintings, he satisfied the need in America for lasting images of its early national leaders created in an international language of portraiture. Stuart created three portrait types for the president: a bust length facing left (the so-called Vaughan image), another facing right (the Athenaeum version) and a full-length composition (the Lansdowne). The exhibition brings together several of each type, including four full-lengths. These grand paintings have never before been seen side by side.

The display will engage viewers by showing the variations in Stuart’s signature work, which Stuart continued to replicate for the next 30 years and will explain the genesis of the portrait that most know so well as the face on the US $1 bill.

A complementary exhibition “George Washington: Man, Myth, Monument – Images from the Metropolitan” will feature some four dozen works in all media depicting America’s first president and will be on view in the museum’s American wing until February 27.

After its showing at the Metropolitan, “Gilbert Stuart” will be on view at the National Gallery of Art in Washington, D.C. March 27-July 31.

The Metropolitan Museum of Art is at 1000 Fifth Avenue. For information, 212-535-7710.