15 Insider Tips from Caricature Artists

When you hear the term caricature, you might picture street artists on bustling boardwalks or near museums, crafting quick, amusing sketches of passersby, often leaving their subjects either thrilled or slightly embarrassed. However, the world of exaggerated illustrations goes far beyond these casual encounters, blending artistry with humor in ways that transcend mere novelty. We consulted three seasoned professionals to uncover their favorite and least favorite subjects, the tricks that make their work more challenging, how they handle dissatisfied clients, and the subtle signs that someone truly doesn’t want to be sketched.

1. THEY WANT YOU TO REALIZE ITS HISTORY RUNS DEEP.

Many of history's most renowned artists honed their craft through caricature. Eileen Owens, curator of "Biting Wit and Brazen Folly: British Satirical Prints, 1780s–1830s" at the Philadelphia Museum of Art, notes that Leonardo da Vinci pioneered the use of caricature in his notebooks, filled with “grotesque” sketches of peculiar faces and heads. (Giorgio Vasari, his 16th-century biographer, wrote that Leonardo was so fascinated by unique heads—bearded or hairy—that he would trail such individuals for an entire day.) Renaissance artists often turned to caricature as a playful diversion from their demanding training: "It involved exaggerated features like oversized noses and wild hair, a way to mock facial traits. Mastery of drawing was essential to exaggerate effectively," Owens explains.

Caricature flourished in late-17th century Italy, where Pier Leone Ghezzi began creating humorous sketches mocking affluent Romans and tourists, as Owens describes. The trend then spread to Britain, where it became immensely popular, leading to the establishment of publishing houses dedicated solely to caricature prints. These publishers also rented out portfolios of caricatures daily and displayed prints in their windows, drawing crowds eager to see satirical depictions of figures like a foolish Napoleon or ridiculous high-society trends. Owens compares this to modern-day gossip magazines: "It was like the People magazine of its time."

2. MANY OF THEM ARE SELF-TAUGHT.

Many caricature artists are self-taught, largely due to the limited availability of specialized training. Illustrator Tom Richmond, known for his movie parodies in MAD Magazine, explains, "Very few art schools include cartooning or caricature as a significant part of their curriculum, making it difficult to find formal instruction. Caricature is a niche and varied art form; it can't be taught like comic drawing, which involves storytelling techniques, sequential art methods, and a more structured approach." Richmond emphasizes the importance of adapting one's artistic skills to caricature, encouraging artists to fully embrace their unique style, regardless of how they practice.

3. IT CAN BE GREAT TRAINING FOR OTHER ART FORMS.

Richmond often advises students at his nationwide workshops to experiment with live drawing, regardless of their artistic focus. He suggests activities like volunteering at local events or sketching at daycare centers. This practice, he explains, hones an artist's ability to capture gestures, body posture, and weight distribution—skills that differ significantly from the meticulous shading done over hours. Returning to longer projects afterward, artists develop a sharper eye for details they might have previously overlooked, making it an excellent exercise for refining their observational skills.

4. THEY’RE NOT (NECESSARILY) OUT TO MOCK YOU.

Caricatures are often described as "portraits with the volume turned up," but they don’t have to be cruel. Richmond emphasizes that caricature is about humor with a purpose: "It’s not just about exaggerating features for laughs; it’s about capturing a person’s essence and telling a story through their presence." He adds that his goal isn’t to distort noses or chins but to understand the individual’s personality and amplify it in a way that feels authentic and engaging.

"My aim is to bring smiles or laughter," says CeCe Holt, who works at events and amusement parks and serves as business manager for the non-profit International Society of Caricature Artists (ISCA). "I never want to upset anyone."

5. THEY DON’T SWEAT IT WHEN SOMEONE DOESN’T LIKE THEIR LIKENESS …

Even though caricaturists aim to capture your true essence, it doesn’t guarantee you’ll appreciate the result. People often have a skewed perception of their appearance, whether it’s their weight, facial features, or even something as specific as freckles. Holt notes that partygoers rarely complain about their caricatures since they aren’t paying directly. However, when an amusement park visitor objects, her response is simple: "I apologize and move on to the next person."

Richmond shares a similar attitude, acknowledging that in quick, low-cost sketches, not every portrait will be a hit. "Occasionally, someone refuses to pay or demands a refund later. Live caricature can be unpredictable, which is why I prefer collaborating with art directors," he says.

6. … BUT SOMETIMES CUSTOMERS RETALIATE.

Sometimes, customers fight back. Ipecacxink, a caricature artist at a Midwest theme park, shared in a Reddit AMA about a boy who was deeply upset by her drawing. "I took a lunch break right after finishing it. While I was away, he returned and drew a circle with spiky hair, glasses, and angry eyebrows, along with a note saying, 'How do you like being made fun of?!' He left it on my chair. It was so funny that I kept it," she recalls.

At Sardi's, the iconic Times Square restaurant famous for its wall of caricatures, some celebrities have been so displeased with their depictions that they demanded their portraits be removed, according to the owner in an interview with AMNew York. In the past, the in-house artist (compensated with meals rather than cash) would show unfinished sketches to the subjects for approval before adding exaggerated features. This practice has ceased, and today, the caricatures lean more toward realistic portraits, reducing friction between the restaurant and its high-profile guests.

7. THEY CAN DO PORTRAITS IN AS LITTLE AS THREE MINUTES.

At amusement parks like Worlds of Fun in Kansas City, Missouri, Holt strives to complete black-and-white sketches in just three minutes. For wedding receptions, where she adds color, she caps her time at six minutes. Speed is essential to accommodate as many guests as possible. "You have to work quickly, or people will walk away," she explains.

Holt emphasizes that speed requires trusting her instincts without hesitation. Richmond adds that quick sketches help caricaturists develop a "sixth sense" for capturing expressions: "You learn to read people—whether they’re lively and extroverted or reserved and quiet." This skill often involves highlighting distinctive traits: "Friends watching will say, 'That’s his smile! You nailed it!'" Richmond notes.

8. BORING-LOOKING CUSTOMERS ARE THE HARDEST.

Caricaturists dread drawing customers with completely average features. "Many are surprised to learn that the most challenging subjects are those who look entirely ordinary," says GertrudisSlugworth, a theme park caricaturist, on Reddit. "When I encounter someone with no standout features, I focus on their clothing, hairstyle, or accessories to create a recognizable likeness."

Conversely, naturally unique individuals are often favorites. Richmond mentions Slash, the Guns N’ Roses guitarist, as a prime example: "He’s already visually striking—just glasses, hair, and a top hat. You don’t need to exaggerate much. You can depict him with his guitar low or capture his signature head tilt, which reflects his personality as a musician."

9. THEY MAY CHANGE THEIR TECHNIQUE TO SUIT THE WAY YOU LOOK.

Early in her career, Holt admits she felt uneasy sketching individuals who weren’t thin, fearing they might misinterpret her work as offensive, despite her good intentions. Over time, she developed a method using soft lines that gradually thicken toward the base of the face. This approach creates a result that’s "adorable yet still recognizable," Holt explains.

GertrudisSlugworth notes that when drawing individuals with noticeable physical differences, she often opts for a more realistic style rather than exaggeration, which is typically central to caricature. "I adjust based on their demeanor. If it’s something simple, like a missing eye, they might request to be drawn as 'normal.' Most people are aware of their unique traits and appreciate an honest depiction," she shares.

10. STREET ARTISTS HAVE AN ADVANTAGE.

Richmond points out that artists sketching live subjects, such as those stationed outside museums, have a distinct advantage over him. He often relies on photos, which lack the dynamic gestures and personality of a live model. "When I work from 2D images, I’m limited to what the photo captures, which feels shallow and incomplete," he explains.

Holt shares this sentiment: "Drawing from photos is entirely different than capturing the essence of a person in real time." When clients request caricatures based on photos, she insists on multiple images, particularly full-body shots, to better understand posture and personality.

11. THEY'RE INCREASINGLY IN DEMAND.

Richmond observes that while traditional newspaper cartoonist roles are declining, editorial cartooning—which frequently incorporates caricature—is thriving. He attributes this partly to the current political climate but also to a broader need: "Most media stories, whether TV shows or articles, revolve around people and require visual representations. Caricature offers a unique, humorous touch that cameras can’t replicate," he says.

12. THERE'S A CARICATURIST CONVENTION.

Each November, the ISCA organizes an annual convention that attracts caricaturists globally. The event features guest speakers, workshops, and live demonstrations, but the highlight is a multi-day competition where artists sketch each other for awards in categories like best use of color and most humorous portrayal. (The top prize is the Golden Nosey.) Richmond describes the diversity of styles as "incredible," ranging from acrylics and pastels to airbrushing and sculpture. Holt adds that one artist even uses ink-spitting as a technique.

13. THEY MIGHT HIDE THINGS IN THEIR PORTRAITS.

Richmond admires the late Al Hirschfeld, who famously concealed his daughter’s name, Nina, within his iconic The New York Times cartoons. (Hirschfeld would note the number of hidden Ninas in his signature, turning it into a reader’s puzzle.) Ipecacxink shares her own quirks: "I used to sneak tiny self-portraits into the pupils of my subjects or include a radioactive symbol as a nod to our neon yellow work shirts, which made me feel like we were glowing with radiation."

14. THEY CAN TELL WHEN YOU DON'T WANT A DRAWING.

Sometimes, a parent, friend, or partner buys a caricature for someone who isn’t enthusiastic about it. In such cases, the artist can usually sense the lack of interest: "They avoid eye contact, refuse to smile, or sit awkwardly," ipecacxink explains. "I always handled it professionally—engaging in conversation if they were willing, staying quiet if not, and smiling warmly at the end. My goal was to keep things friendly to ensure they didn’t walk away without paying."

15. THEY MIGHT BE SWAPPING THEIR PENCILS FOR A TABLET.

While some caricaturists still use traditional methods like paint, markers, or colored sticks, many have embraced digital tools to meet the demands of modern publications. Holt, for instance, often works on an iPad Pro with an Apple Pencil in Procreate, while Richmond now completes all his coloring digitally. "Tablets are incredibly convenient—unlimited paper, no need to sharpen pencils, and all your tools fit in a small bag," he says. "But the creativity still comes from the artist. Technology can’t replace that."