In over forty years of drawing 'humorous portraits', the comments I hear most often are "I'd LOVE to make these, but I can't draw," and "How do you learn how to do caricatures?" Let me say, ANYONE can learn to draw, but just because the portraits are humorous doesn't mean you don't have to know 'the rules' of portraiture to create them! As with any skill, it takes practice and a knowledge of the subject to get more than a 'that's nice...but who IS it?' reaction. I recommend buying a good pencil, a LOT of paper, and these two books, to start; The New Drawing on the Right Side of the Brain , by Betty Edwards, is an invaluable tool that helps you learn how to 'interpret' what your eyes 'see'; and The Natural Way to Draw: A Working Plan for Art Study , by Kimon Nicolaides, has provided generations of artists a comprehensive step-by-step lesson plan on mastering heads and figures. If you faithfully follow the guidance these books provide, I GUARANTEE your skills will develop, and improve!
After you've developed 'an eye' for faces, I'd move on to How To Draw Caricatures , by Lenn Redman, a terrific volume on how to 'bend' the rules, and create humorous portraits that will exaggerate yet flatter your subjects (an important thing to remember!). Caricatures: Everything You Need to Know to Get Started (Collins Learn to Draw) , by Alex Hughes, is an easy-to-follow guide to Traditional Caricature; Let's Toon Caricatures , by Keelan Parham, Big Book of Cartooning , by Bruce Blitz, and Draw Caricature: Techniques*Facial Basics*Projects , by Steve Chadburn, Noel Ford, and Pete Dredge are also excellent; Alex, Keelan, Bruce, and Steve are longtime friends and friendly competitors of mine, and have great 'track records', training caricaturists!
Ready to move up, and face the competitive caricature market? There are two inexpensive, terrific resource books I'd recommend: How to Draw and Sell Cartoons: All the Professional Techniques of Strip Cartoon, Caricature and Artwork Demonstrated , and How to Be a Successful Cartoonist ; each 'breaks down' down the business of drawing into a 'doable' gameplan! Remember, it isn't enough just to be able to draw; you have to be able to market your skills, as well, if you plan to do more than just entertain friends and family!
After all is said and done, the most important rule in learning how to draw is to DRAW! If you are willing to really practice (and that doesn't mean 'doodle' a few minutes, while you're in class or on the phone!), and seriously utilize the tools the authors of these wonderful books offer, I PROMISE you'll be able to join my fraternity of artists, the Caricaturists!
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