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Bob Mankoff: The Persistence and Wit That Shaped Cartoons

Bob Mankoff: A Journey of Persistence and Creativity in the Cartoon IndustryIn the world of humor and wit, there are few who have made as big an impact as Bob Mankoff. From his relentless pursuit of getting published in the renowned New Yorker to his experimentation with stand-up comedy, Mankoff’s persistence and creativity have propelled him to the forefront of the cartoon industry.

In this article, we will delve into the fascinating journey of Bob Mankoff, exploring his remarkable rise to fame, his signature style, and the inspiration behind his hilarious cartoons. Bob Mankoff’s persistence and creativity in the cartoon industry

Mankoff’s journey to getting published in the New Yorker

Aspiring cartoonists dream of having their work grace the pages of the illustrious New Yorker, but only a select few ever achieve this feat.

Mankoff’s path to success was no different. With a rejection rate that would have discouraged many, he persevered, never giving up on his dreams.

Finally, in 1977, Mankoff’s persistence paid off when one of his cartoons made it into the pages of the New Yorker. This breakthrough opened the doors for countless more cartoons to be published, solidifying his position as an esteemed cartoonist.

Mankoff’s experimentation with stand-up comedy

While Mankoff’s talent for drawing humorously captivating cartoons was apparent, he wanted to explore new avenues for making people laugh. This led him to try his hand at stand-up comedy, a daunting challenge for anyone seeking to elicit laughter in person rather than through a static illustration.

To everyone’s surprise, Mankoff discovered that he was not only a talented cartoonist but also a skilled comedian. His unique ability to blend humor and drawing soon became his trademark, making him a formidable force in both the cartoon and comedy worlds.

Mankoff’s signature style and inspiration

Mankoff’s research and inspiration for his signature dot style

One cannot mention Bob Mankoff without acknowledging his distinctive dot style, reminiscent of the French Impressionist painter Georges Seurat’s technique of stippling. Mankoff’s fascination with Seurat’s work and his use of dots to create depth and texture inspired him to experiment with the same technique in his cartoons.

Through extensive research and countless hours spent meticulously dotting, Mankoff developed his signature style, instantly recognizable and celebrated by cartoon enthusiasts worldwide. Mankoff’s famous and widely reproduced cartoon

Among the many cartoons created by Mankoff, there is one that stands out as his most famous and frequently reprinted.

In this particular cartoon, Mankoff depicts himself examining a book titled “How to Draw Cartoons.” The caption reads, “This is it, the complete works of every cartoonist who’s died broke, anonymous, and bitter.” This self-referential and autobiographical cartoon resonates with many aspiring artists and serves as a reminder of the challenges faced by those pursuing a career in the creative industry.


Bob Mankoff’s journey through the cartoon industry is a testament to the power of persistence and creativity. From facing numerous rejections to becoming a household name, Mankoff’s unwavering dedication to his craft has left an indelible mark on the world of humor and illustration.

His signature dot style continues to inspire and entertain, while his famous cartoon serves as a poignant reminder of the struggles faced by artists. Bob Mankoff stands as a shining example of what can be achieved when talent, persistence, and creativity combine.

Mankoff’s success and career in cartooning

Mankoff’s role as the humor and cartoon editor of Esquire

Bob Mankoff’s success as a cartoonist extended beyond the pages of the New Yorker. In 1997, he took on a new role as the humor and cartoon editor at Esquire magazine.

This position allowed him to further expand his influence and showcase his talent for discovering and promoting comedic genius. Mankoff’s keen eye for humor and his ability to recognize cartoons that would resonate with readers made him an invaluable asset to Esquire, and he played a pivotal role in shaping the humor section of the magazine.

Under Mankoff’s leadership, Esquire’s humor section became a breeding ground for fresh and innovative voices. He actively sought out new talent, nurturing and guiding them in their quest for comedic greatness.

Through his mentorship, Mankoff helped launch the careers of many aspiring cartoonists, paving the way for a new generation in the cartoon industry. Mankoff’s other organizations and digital presence

In addition to his work at Esquire, Mankoff founded Cartoon Bank, a platform dedicated to preserving and showcasing the best cartoons from around the world.

Cartoon Bank provides access to an extensive collection of cartoons, offering a unique opportunity for enthusiasts to explore the rich history of this art form. Through Cartoon Bank, Mankoff aims to celebrate cartoons as a form of artistic expression and provide a platform for both established and emerging cartoonists to reach a wider audience.

In recent years, Mankoff has also embraced the digital landscape, recognizing the power of technology in expanding the reach of cartoons and humor. He co-founded CartoonCollections.com, an online platform that allows users to browse and license cartoons for various purposes, from presentations to publications.

This digital venture bridges the gap between traditional print media and the digital world, making cartoons more accessible than ever before. Mankoff’s digital presence extends beyond his ventures.

He is an active proponent of utilizing technology, particularly artificial intelligence (AI), in the creation and dissemination of cartoons. He has collaborated with AI researchers and developers to explore the potential of AI-generated cartoons.

Mankoff firmly believes that technology can enhance the creative process, allowing for more diverse and innovative forms of humor to flourish.

Lessons to learn from Mankoff

Humor and satire in art and captions

One of the most notable aspects of Mankoff’s cartoons is their ability to seamlessly blend humor and satire. Through his drawings and witty captions, he tackles a wide range of topics, from the absurdities of everyday life to societal and political commentary.

Mankoff’s cartoons serve as a reminder of the power of humor as a tool for social critique and commentary. They demonstrate the impact that a well-crafted cartoon can have in prompting reflection and generating discussions on important issues.

Grit and perseverance in Mankoff’s rise to success

Bob Mankoff’s journey to becoming a renowned cartoonist was not without its share of challenges and failures. Rejection after rejection could have discouraged many, but Mankoff’s grit and perseverance kept him going.

His unwavering belief in his talent and his relentless pursuit of his goals led him to achieve incredible success in the cartoon industry. Mankoff’s story serves as a reminder that persistence and resilience are key ingredients for success in any creative endeavor.

Mankoff’s advocacy for digital and AI projects

Mankoff’s embrace of digital platforms and his collaboration with AI developers highlight his forward-thinking approach to the cartoon industry. He recognizes the potential that technology holds in expanding the horizons of cartoons, making them more accessible, and pushing the boundaries of artistic expression.

Mankoff’s advocacy for digital and AI projects encourages artists to explore new avenues and embrace innovation, ensuring that cartoons remain relevant and impactful in the ever-evolving world of media. In conclusion,

Bob Mankoff’s career in cartooning is a testament to his persistence, creativity, and dedication to the art form.

From his early struggles to his rise to prominence, he has left an indelible mark on the cartoon industry. Through his work as the humor and cartoon editor of Esquire, his founding of Cartoon Bank, and his ventures into the digital realm, Mankoff has continued to shape and redefine the landscape of cartoons.

His emphasis on humor and satire, his unwavering determination, and his embrace of technology serve as invaluable lessons for aspiring artists. Bob Mankoff’s legacy will continue to inspire and entertain generations to come.

Bob Mankoff’s journey in the cartoon industry highlights the power of persistence, creativity, and embracing new avenues. From his early struggles to the pages of the New Yorker and his role at Esquire, Mankoff’s influence expanded through platforms like Cartoon Bank and CartoonCollections.com.

His signature style and irreverent humor inspired generations, while his advocacy for technology and AI projects pushed the boundaries of artistic expression. Mankoff’s story teaches us the importance of resilience, humor, and embracing innovation in pursuing our creative passions.

His legacy will continue to inspire and entertain, reminding us that success in the art world is achieved through a combination of talent, perseverance, and adaptability.

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