American presidents have long been immortalized in paintings, from formal White House portraits to bold, modern reinterpretations. These iconic paintings aren’t just art - they're time capsules of leadership, legacy, and national identity.
Whether you’re a history buff, an art lover, or just a proud patriot, presidential portraiture reveals as much about the artist as it does about the man behind the desk.
So let’s dive in: Here are the 10 best American president paintings ever - starting with a bold, modern favorite that redefined the genre.
1. Steve Penley’s George Washington
The Most Patriotic Presidential Painting of the Modern Era
If there’s one artist who knows how to blend pop culture with patriotism, it’s Steve Penley. His explosive portrait of George Washington, with its vibrant reds, electric blues, and expressive brushwork, captures the spirit of America like no other. Unlike the stoic oil portraits of the 18th century, Penley’s Washington is alive - bursting with energy, courage, and defiance.
Penley’s style is unmistakable: think Warhol meets Americana. He’s made a name for himself painting presidents from Lincoln to Reagan, but his Washington remains the most iconic. This isn’t just wall art - it’s a modern-day tribute to America’s first and fiercest leader.
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2. Gilbert Stuart’s George Washington (The Athenaeum Portrait)
🖌️ The Face on the Dollar Bill
You know this one - even if you don’t realize it. Gilbert Stuart’s unfinished 1796 portrait of Washington became the model for the U.S. $1 bill and countless schoolroom posters. Despite being incomplete, it’s one of the most widely reproduced paintings in American history.
The calm, composed expression became the standard for presidential dignity. But don’t let its formality fool you - Stuart’s work influenced generations of portrait artists to come.
3. Kehinde Wiley’s Barack Obama (Smithsonian National Portrait Gallery)
🌿 Where Contemporary Cool Meets Classical Style
When the Smithsonian unveiled Wiley’s portrait of President Barack Obama in 2018, it broke the internet - and tradition. Sitting forward in a floral jungle of symbolism, Obama appears thoughtful, powerful, and grounded.
Wiley, known for elevating Black subjects in classical poses, flipped the genre on its head. It’s the most talked-about presidential portrait of the 21st century - and proof that modern art belongs in political spaces.
4. Abraham Lincoln by George P.A. Healy
📜 The Pre-Civil War Power Pose
Painted just before Lincoln took office in 1860, Healy’s portrait captures a rare mix of humility and gravitas. The future emancipator is shown mid-thought, perhaps already carrying the weight of a nation about to divide.
This work became one of Lincoln’s favorites - and inspired the famous seated statue at the Lincoln Memorial.
5. Franklin D. Roosevelt by Elizabeth Shoumatoff (The Unfinished Portrait)
🖋️ Frozen in Time
This haunting watercolor was being painted when FDR died suddenly of a cerebral hemorrhage in 1945. The artist never finished it. The soft colors, gentle expression, and abrupt ending all serve as metaphors for the final chapter of one of America’s longest-serving presidents.
Despite its incompletion, it hangs in the Little White House in Warm Springs, Georgia - and remains one of the most emotionally powerful portraits of any U.S. president.
6. Steve Penley’s Donald Trump
🔥 Pop Art Meets Political Firepower
Steve Penley doesn’t shy away from controversy - and his portrait of Donald J. Trump is just as loud and fearless as the 45th president himself. Using vivid reds, stark whites, and electric blues, Penley captures Trump with a raised eyebrow and steely determination. This painting isn’t just pop art - it’s political energy on canvas.
Whether you love him or loathe him, this portrait demands attention and cements Penley’s place as the most influential pop art presidential painter of the modern era.
7. Norman Rockwell’s "The Problem We All Live With" (Featuring JFK)
✊ A Presidential Portrait Through Action
While not a traditional portrait, this powerful 1964 painting by Norman Rockwell features President John F. Kennedy in a behind-the-scenes way. It depicts 6-year-old Ruby Bridges being escorted to an all-white school - an image so moving that JFK requested it be displayed in the White House during the Civil Rights era.
This painting shows that a president’s influence isn’t always in their face - but in the movements they champion.
8. Robert McCurdy’s Barack Obama (White House Portrait)
🕴️ Precision, Stillness, and Presidential Focus
Unveiled in 2022, McCurdy’s hyper-realistic portrait of Obama is striking for its simplicity. No chair, no flag, no background clutter - just the man, standing tall in a crisp suit against a white background. The image forces you to focus on Obama’s gaze, posture, and presence.
It’s a masterclass in minimalist presidential portraiture - a bold departure from tradition.
9. Herbert Abrams’ Jimmy Carter (White House Collection)
🌾 Down-to-Earth and Determined
Abrams painted Carter in a casual gray suit, standing in front of his desk with sleeves rolled up. The portrait reflects Carter’s humble, hands-on leadership style, and breaks from the pomp often seen in presidential imagery.
It’s approachable, real, and full of personality - just like Carter’s legacy.
10. Aaron Shikler’s John F. Kennedy (White House Collection)
🕊️ Head Bowed, Eyes Cast Down
Shikler’s 1970 portrait of JFK is somber and introspective - arms crossed, head tilted, eyes lowered. Commissioned after Kennedy’s assassination, the family requested a non-traditional pose to reflect the weight he carried.
It remains one of the most emotionally resonant portraits of any American president—elegant, quiet, and unforgettable.
The TLDR on Greatest Presidential Paintings Ever (Updated for 2025)
From Penley’s explosive color to Shikler’s quiet elegance, the best American president paintings do more than document history - they reflect it. They show us power, personality, and even pain. And in this era, no one captures those themes with more edge and emotion than Steve Penley.
If you're building a collection, curating content, or just craving inspiration—these paintings are proof that great leadership deserves great art.
🇺🇸 Discover presidential portraits reimagined for the modern age at PenleyArtCo.com