Perhaps Hals’s most famous work, The Laughing Cavalier, painted in 1624, is pure swagger. Though the sitter isn’t actually laughing—and wasn’t truly a “cavalier," his confident pose, lavish costume, and teasing gaze made him unforgettable.

In the video below, my favorite British art critic Waldemar Januszczak says Frans Hals had a real gift for "painting people exactly as they were, messy hair, crooked smiles, little smirks and all."

Frans Hals’s The Laughing Cavalier is basically the Dutch Golden Age’s rock-star portrait. Painted in 1624, it shows a stylish young guy in a flashy outfit and cocky pose, hand on his hip, giving you a look that feels more teasing than serious.

Other works like The Merry Drinker and Peeckelhaeringh (Pickled Herring) celebrate boisterous theatrical types and barroom bravado, while La Bohémienne (Gypsie Girl) offers a mischievous, uncommissioned study of personality rather than respectability.

Hals also brought warmth and dignity to working figures. In Man with a Beer Jug, a rugged fisherman turns toward us as if mid-toast. His weathered face comes alive, with rosy cheeks and an endearing grin.

One of Hals’s most historically significant portraits is Pieter van den Broecke, a Dutch merchant and admiral of the Dutch East India Company who helped introduce coffee to Europe. Hals presents him as confident, worldly, and energetic, a celebration of the merchant class that fueled the Dutch Golden Age.

Later portraits, like Willem van Heythuysen, a wealthy fabrics merchant, show success without swagger: relaxed, assured, and entirely at ease.

Malle Babbe portrays a real woman from Haarlem, known locally as “Crazy Babbe." With her wild grin, beer mug, and owl companion, a symbol of drunkenness, Hals captures her not with cruelty, but with humor and humanity.

In his eighties, Hals painted Portrait of an Unknown Man, once thought to depict a disreputable figure. Later research revealed his attire was fashionable, reminding us how easily modern assumptions can misread the past.

Hals’s influence rippled forward through centuries. James McNeill Whistler reportedly insisted on touching Hals’s paintings, wanting to feel the surface itself. Vincent van Gogh praised Hals as “a colorist among colorists,” marveling at his vibrant use of black.

One of Hals’s greatest late works, The Regentesses of the Old Men’s Almshouse, shows the women who governed Haarlem’s charity. Stripped-down, bold, and unsentimental, it proves Hals was still pushing his art to the limit near the end of his life.

John Singer Sargent revered Hals’s technique, calling him one of the greatest oil painters who ever lived. Sargent even copied The Regentesses and kept it prominently displayed in his studio as a touchstone for his own work. Sargent once said, “It is hard to find anyone who knows more about oil painting than Frans Hals.”

Though Norman Rockwell never wrote about Hals, visual echoes suggest he studied Hals’s group portraits while preparing The Art Critic.

Frans Hals’s Meeting of the Officers of the St. Adrian Militia Company shows a lively group snapshot of Haarlem’s civic pride during the Dutch Golden Age. Hals shows these officers relaxed in a courtyard, chatting, seated, and standing with their weapons and bright sashes on display. Each face feels different and alive, turning what could have been a formal commission into a scene that still feels like a real gathering of leaders who appear to enjoy each other's company.

When American painter William Merritt Chase traveled through Europe in the early 1900s, he made a point of stopping in Haarlem to soak up the work of the Dutch masters. He was really drawn to The Officers of the St. Adrian Militia Company, especially the commanding officer, Colonel Johan Claeszoon Loo.

Nearly 240 years after Hals, Chase decided to have a little fun. Instead of making a straight copy of this painting, he dressed himself up in costume and painted his own Self-Portrait as Colonel Johan Claeszoon Loo. The result is part tribute, part performance, a playful nod to Hals’s swaggering style and his ability to paint his subjects as breathing and alive.

Frans Hals painted people as they were, laughing, drinking, flirting, governing, aging, and living their lives in real time. His genius wasn’t just technical; it was deeply human. With fearless brushwork and an unmatched feel for personality, Hals collapsed the distance between past and present. Four hundred years later, his subjects still feel close enough to meet, toast, and laugh with. That is his greatest legacy.