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Sketching the Outline
Draw a circle. Sketch an evenly proportioned circle near the upper edge of the paper. Draw a horizontal line across the bottom quarter of the circle. This circle will act as a guide for the shape of Deadpool's head.
Extend the figure. Draw an elongated curve beneath the bottom of the circle, then draw a vertical line down the center of the entire structure. This curve will act as a guide for his jaw and chin. The curve should connect to the circle at both ends of the horizontal guideline, and the bottom should be somewhat narrowed. The vertical span of this curve should nearly match the height of the original circle. Draw the vertical guideline down the center of the face if you want a front-facing sketch. For an angled sketch, you'll need to position the vertical guideline further to the side facing away from the viewer.
Sketch out the neck and shoulders. Lightly draw two vertical lines extending down from either side of the chin curve. Draw a diagonal line coming off each of these vertical lines. The two vertical lines should start slightly above the vertical middle of the chin curve, and they should stop shortly before the bottom of the same curve. These two lines will form the character's neck. The two diagonal lines should point downward and away from the head. They should begin two-thirds down the neck lines and be approximately three-quarters the diameter of the head. Together, these two lines form the shoulders.
Place the eyes. Draw two pointed ovals, placing them in between the bottom edge of the head circle and the enclosed horizontal guideline. These will become the eyes, and they should have a horizontal, narrow football-shape. Make both eyes the same size if creating a front-facing sketch. Each eye should be roughly one-sixth as wide as the head circle. For an angled sketch, make the "closer" eye slightly larger than the "further" eye. Place each eye oval an equal distance away from the vertical guideline. Each eye should also should hit the enclosed horizontal guideline.
Defining the Features
Correct the shape of the face. Trace back over the outer perimeter of the entire face structure (head, jaw, and chin). Add more definition to the face where appropriate. Draw a small triangle at the top of the head, placing it next to one side of the vertical face guideline and pointing the tip of the triangle away from the same vertical line. This small peak represents the crease of Deadpool's mask. Flatten the curves of the initial head circle so that the sides of the face seem straight. Add small, shallow curves to each side, starting at the horizontal face guideline and extending down over the top quarter of the chin curve. These new curves will become his ears. Angle the chin curve, making it narrow at a sharper angle as it reaches the bottom. Flatten the bottom of the curve to give the character a sturdy, square-like jaw.
Refine the shape of the eyes. Trace back over each eye. Follow the same basic shape, but make one eye wider than the other. Expand the top curve of the right eye to make the overall eye appear wider. Keep the oval shape of the left eye along its outer edge, but sharpen the inner end of the same eye so that it forms a more narrow point toward the inside of the face. Doing this gives the shape of the eyes a more expressive appearance. If desired, you could also swap the two eyes, making the right narrow and the left wide.
Add brow lines around the eyes. Sketch a line above each of the eyes to mimic the brow bone. Add two smaller lines beneath each eye to complete the bone structure of the eye space. The outer portion of each upper brow line should start shortly before the outer point of the eye and just slightly above it. For the brow above the wide eye, follow the basic curve of the eye until you reach the inner eye point. At that point, draw an upward curve that extends toward the vertical face guideline while pointing away from the eye. For the brow above the narrow eye, follow the basic curve of the eye but gradually move the brow down as it reaches the inner tip of the eye. The brow curve should touch at the inner eye tip, then curve upward and away from the eye like the other brow does. For the two small lines beneath each eye, simply draw a small downward diagonal dash. It should start near the inner corner of each eye and point away, extending only one-third the length of the eye.
Sketch out the eye portion of the mask. Draw a large, vertical oval around each eye to create the eye portion of the character's mask. Each oval should extend from the vertical middle of the original circle down to the vertical center of the chin curve. Technically, these should not be perfect ovals. The outer side of each patch should curve like a proper oval, but the inside should be wider; the top and bottom lines of the inside should meet at the patch's vertical center in a wide, curved point.
Draw two horizontal lines around the neck. Sketch the first line from the lower endpoint of one neck line to the lower endpoint of the other neck line. Place the second line above the first. Both lines should curve slightly upward, and the two should run parallel to one another. The middle third of the top line should be hidden beneath the character's chin. Overall, the line should extend over the vertical middle of his neck.
Define the neck. Draw a pair of inward diagonal lines extending down from the right of the collar. Mirror this pair on the left side. The inner line of each pair should start at the edge of the chin, and the outer line of each pair should be halfway between the inner line and the edge of the neck outline. Both lines in each pair should run parallel to one another and match the angle of the chin on that side of the face.
Define the collarbone. Sketch a nearly horizontal line beneath each neck line. These lines should extend from the inside of each inner neckline to a point just outside the original neck perimeter guidelines. Each line should be nearly horizontal, but it should actually fall at a gradual downward angle from the outside to the inside. At the inside end of each line, draw a sharper, small line pointing down and inward. These sharper lines should roughly match the angle of the inner neck lines.
Adding Weapons
Draw long diagonals above the shoulders. Sketch a long diagonal line starting at the upper left shoulder guideline. Mirror this line on the upper right shoulder guideline, too. Each diagonal should extend upward and away from the head. Start the diagonal roughly one-fifth down from its respective shoulder. Extend it upward at an approximate 30-degree angle until a point just beneath the top of the head. These two lines will become the guidelines for Deadpool's katanas.
Define the hilts. Place a short horizontal line across one-seventh of the bottom katana guideline. Draw a rectangle around the top sixth-sevenths of the guideline. Repeat for both sides. The short horizontal line will be the guard of the hilt, and the rectangle will be the hilt itself. The rectangle should follow the angle of the original guideline, but it should be less wide than the horizontal guard line. Draw a second horizontal line inside the hilt rectangle near the top. This will be the pommel of the hilt.
Expand the lower portion of each katana. Draw a second horizontal line just beneath each original guard line. Place two vertical lines beneath this new horizontal line, extending them down from the guard to the shoulder. Close the sides of the upper and lower guard lines to complete the guard shape. The vertical lines should roughly match the size of the hilt lines, and they should follow the angle of the original guideline. Together, these lines form the sword sheaths.
Finalizing the Drawing
Trace the permanent lines. Trace over the permanent lines of the character. Press harder to make the lines darker and more defined. The permanent lines include any line that defines some feature of the character. You can use a pencil or an ink pen, but if you use ink, make sure that the ink dries completely before continuing.
Erase the temporary guidelines. Once you define the permanent lines, go back through and erase any temporary guideline you no longer need. This includes the guidelines of the katanas, the bottom of the face circle, and the vertical and horizontal guidelines inside the face. It also includes any unnecessary line segments that remained after redefining the shape of his face, neck, and shoulders.
Add color, if desired. You can leave this drawing as a simple sketch, but you could also add color if you wish to do so. If you do add color note that the main portion of the mask and neck will be red. The collar and eye portion of the mask should be black. The swords should also be black or dark gray.
Admire your drawing. Congratulations! You've just finished drawing Deadpool.
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