A portrait of Teddy Roosevelt was painted by perhaps my favorite portrait artist, Anglo-American John Singer Sargent.
My favorite Sargent painting is known as "Capri Girl" (1878). My daughter and I saw it on display at the Seattle Art Museum and we stood admiring it for several minutes.
The other President Roosevelt, FDR, was captured by two artists in 1945, the year of his death. Douglas Chandor's version, painted in March of 1945, is one of the most unusual portraits because the artist chose to paint his hand gestures.
The portrait by Elizabeth Shoumatoff was started a few days prior to FDR's death (12 April 1945) but never finished.
Several artists created images of President John F. Kennedy, including collages by Robert Rauschenberg.
Aaron Shikler's portrait of JFK was painted posthumously.

While visiting the Ronald Reagan Library in 2018, I saw this amazing montage of President Reagan painted by Norman Rockwell.
Simmie Knox's portrait of President Bill Clinton is the first portrait commissioned by an African-American artist. Another beautiful artwork is Kehinde Wiley's portrait of former President Barack Obama.
Slightly out of presidential order is the portrait of President George W. Bush by John Howard Sanden.
I saved Dubya for last because I am in awe of his prolific paintings, which include 66 portraits of veterans. See the book, entitled Portraits of Courage: A Commander in Chief's Tribute to America's Warriors.
Not only was he a great president, but he is a wonderful and prolific artist.
Besides President Bush the Younger, President Ulysses S. Grant was an accomplished landscape painter, Dwight Eisenhauer painted portraits later in life, and even Jimmy Carter dabbled in the visual arts.
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It seems like the more I teach, the more I have to blog about. Please comment and suggest topics you'd like me to post about.